Just before Leo, Brad, Charlize, and Keanu became untouchable, they partied their hearts out in an L.A. free of TMZ and camera phones in every pocket.
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Vintage Hollywood In 48 Photos
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1 of 56Hollywood’s early 1990s power couple, Johnny Depp and Winona Ryder, attend photographer Herb Ritts’ birthday party. Sept. 18, 1990.Barry King/WireImage/Getty Images 2 of 56Keanu Reeves at the premiere for Bill & Ted’s Bogus Journey at the Hollywood Palladium on July 11, 1991.Ron Galella/Ron Galella Collection/Getty Images 3 of 56Mark Wahlberg and Leonardo DiCaprio, who became friends while filming The Basketball Diaries. Nov. 11, 1993.Ke.Mazur/WireImage/Getty Images 4 of 56Angeline Jolie and Peta Wilson hit the dance floor at the 1997 Cable Ace Awards.Twitter 5 of 56Before he was Tyrion Lannister, Peter Dinklage sang in a band called Whizzy, seen performing here circa the early 1990s.Twitter 6 of 56From left, Patrick Dempsey, Richard Grieco, Costas Mandylor, and Christian Slater pal around while celebrating the release of Grieco’s film, If Looks Could Kill, at the Roxbury Club on March 9, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 7 of 56Johnny Depp and Winona Ryder attend the Mermaids premiere one year into their relationship. Dec. 10, 1990.Barry King/WireImage/Getty Images 8 of 56Charlize Theron celebrating her 22nd birthday with Hollywood’s bright new shining star, Leonardo DiCaprio, who was smack-dab in the middle of Titanic superstardom. 1997.Randall Slavin 9 of 56Pauly Shore, Judy Tenuta, and Fabio squeeze some fun out of Shore’s HBO comedy special release party on Aug. 26, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 10 of 56Brooke Shields and Michael Jackson arrive at the 35th Annual Grammy Awards after-party at Jimmy’s Restaurant in Beverly Hills. Feb. 24, 1993.Steve Graniz/WireImage/Getty Images 11 of 56On the set of My Own Private Idaho, Keanu Reeves and co-star River Phoenix hang out while director Gus Van Sant snaps a photo. 1990.Twitter 12 of 56A young Leonardo DiCaprio and Johnny Depp attend the L.A. premiere for What’s Eating Gilbert Grape at the Paramount Theater on Dec. 12, 1993.Ron Galella, Ltd./Ron Galella Collection/Getty Images 13 of 56Patrick Dempsey at the premiere of If Looks Could Kill, starring Richard Grieco, at the Roxbury Club on March 9, 1991.Jim Smeal/Ron Galella Collection/Getty Images 14 of 56Winona Ryder and boyfriend Johnny Depp attend the premiere for The Silence of the Lambs in Century City on Feb. 1, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 15 of 56Keanu Reeves and My Own Private Idaho co-star and friend, River Phoenix. 1990.Twitter 16 of 56Richard Gere, Cindy Crawford, and famous paparazzi photographer Ron Gallela arrive at the 1991 Moving Picture Ball. The night’s event was a tribute to Martin Scorsese’s contributions to cinema. 1991.Frank Trapper/Corbis/Getty Images 17 of 56Will Smith and his The Fresh Prince of Bel Air castmates enjoy the party in celebration of the show’s 100th episode on Sept. 13, 1994.Chris Haston/NBCU Photo Bank/Getty Images 18 of 56Rob Lowe enjoys a cigarette outdoors in Los Angeles. Date unspecified.Barry King/WireImage/Getty Images 19 of 56Cameron Diaz and Milla Jovovich partying on the floor with some friends. 1995.Randall Slavin 20 of 56In the midst of DiCaprio Mania, magician David Blaine and actor Lukas Haas — who were both part of DiCaprio’s notorious “Pussy Posse,” lift their friend up by his legs. Nov. 2, 1995.Patrick McMullan/Patrick McMullan/Getty Images 21 of 56Johnny Depp and gonzo journalist Hunter S. Thompson became fast friends during preproduction for Fear and Loathing in Las Vegas. Here they are holding a reading of Thompson’s work at Depp’s Viper Room club. Sept. 7, 1996.Jeff Kravitz/FilmMagic, Inc./Getty Images 22 of 56"We were at the Viper Room but I met Benicio [Del Toro] a few years earlier when he had a small part in a movie I worked on, Swimming With Sharks," said photographer Randall Slavin. “Next to him is Joseph Kraemer, who has gone on to score films, including many of Chris McQuarrie’s.” 1996.Randall Slavin 23 of 56Richard Grieco and Christian Slater chill out and have a smoke during the If Looks Could Kill premiere at the Roxbury Club. March 9, 1991.Ron Galella/Ron Galella Collection/Getty Images 24 of 56Nicolas Cage and pal Charlie Sheen have a laugh at a party at Bar One Nightclub in West Hollywood. June 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 25 of 56Robert Downey Jr. during his tumultuous rollercoaster of a life in the early 1990s, pictured here at All Star Jam Night at the China Club in West Hollywood. June 26, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 26 of 56Keanu Reeves and David Bowie pose for a photo. 1992.Lester Cohen/Getty Images 27 of 56Leonardo DiCaprio and Brad Pitt pose for a photo at a party on Sept. 15, 1995.Patrick McMullan/Getty Images 28 of 56River Phoenix, K.D. Lang, and Liza Minnelli. Phoenix died two years later at Johnny Depp’s Viper Room club due to a drug overdose. Feb. 1, 1991.The LIFE Picture Collection/Getty Images 29 of 56Batman himself, Michael Keaton, with the Penguin, Danny DeVito, and Catwoman, Michelle Pfeiffer, attending the Batman Returns premiere in 1992.Twitter 30 of 56Kiefer Sutherland and Julia Roberts at Mann’s Chinese Theater for the Young Guns II premiere. July 30, 1990.Jim Smeal/Ron Galella Collection/Getty Images 31 of 56Nicolas Cage has a smoke and a drink with girlfriend Lisa Stothard at the premiere for the David Lynch-directed movie Wild at Heart. Aug. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 32 of 56Marilyn Manson with his new girlfriend Rose McGowan and Twiggy, Manson’s bassist and guitarist. 1997.Randall Slavin 33 of 56Actor Eddie Mills and Reese Witherspoon backstage at the Wiltern after a Counting Crows concert. Witherspoon was in the midst of blowing up, with the Mark Wahlberg-starring Fear having just been released. 1996.Randall Slavin 34 of 56Sting and his wife, Trudie Styler, heading into All Star Jam Night at the China Club. Feb. 12, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 35 of 56Sylvester Stallone, Demi Moore and husband Bruce Willis socializing at their shared business venture, Planet Hollywood. 1990.The LIFE Picture Collection/Getty Images 36 of 56Johnny Depp and his post-Winona girlfriend Kate Moss at the 42nd birthday party for Mickey Rourke — which Johnny Depp organized and paid for. Sept. 25, 1994.Richard Corkery/NY Daily News Archive/Getty Images 37 of 56Mickey Rourke and Johnny Depp at Rourke’s 42nd birthday party, thrown by Depp. Sept. 25, 1994.Lawrence Schwartzwald/Sygma/ Getty Images 38 of 56"[Filming Speed was hard for me to really be serious because he would look at me and I’d be like," said Sandra Bullock before making a swooning face. Keanu Reeves later said, “She obviously didn’t know that I had a crush on her, either.” The pair are pictured here at Planet Hollywood in 1994.The LIFE Picture Collection/Getty Images 39 of 56Cameron Diaz and Edward Norton met in 1998, shortly after he’d been nominated for an Academy Award. The romance didn’t last, and Norton went on to date Salma Hayek. Diaz and Norton are seen partying here in early 1999.KMazur/WireImage/Getty Images 40 of 56Gina Gershon and Rob Morrow attend the Trainspotting premiere after-party. July 15, 1996.Steve Eichner/WireImage/Getty Images 41 of 56Jude Law with actress Samantha Mathis. As photographer Randall Slavin later recalled, Mathis “rented this little house on Hillside, north of Franklin. We had this amazing summer there. When you’re in your 20s and you just all gather at this house — every day, every night.” 1995.Randall Slavin 42 of 56Liv Tyler and Joaquin Phoenix congratulate their friend, Matt Damon, on his success with Good Will Hunting. Dec. 4, 1997.Kevin Mazur Archive/WireImage/Getty Images 43 of 56Kate Moss and Oasis frontman Noel Gallagher, who later admitted, “By 1997 it had just gone berserk. I was doing loads of drugs and me and [bandmate and brother] Liam were just out of control.” Sept. 29, 1998.Dave Benett/Getty Images 44 of 56Arnold Schwarzenegger and Goldie Hawn during a party for Hawn’s Death Becomes Her at Planet Hollywood. July 13, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 45 of 56Brad Pitt and with John Lydon (otherwise known as Johnny Rotten) of the Sex Pistols, heading into a party hosted by David Bowie. Oct. 29, 1995.Ke.Mazur/WireImage/Getty Images 46 of 56Brooke Shields attends a party for Quincy Jones at the Roxbury in West Hollywood. July 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 47 of 56Nicolas Cage and friend Charlie Sheen stick together during a party for Guess Clothing hosted by Claudia Schiffer. Oct. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 48 of 56Corey Feldman attends a Planet Hollywood party in 1993.Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images 49 of 56Photographer Randall Slavin explained that Jeremy Davies (on Paul Rudd’s shoulders) just wrapped a guest spot on Buffy, and was super excited. “Then he got cut and was crushed.” Here they are at a Hole show, letting loose. 1996.Randall Slavin 50 of 56Glenn Close and Woody Harrelson at a performance of the play Brooklyn Laundry at the Coronet Theatre in West Hollywood. April 25, 1991.Ron Galella/Ron Galella Collection/Getty Images 51 of 56Judd Nelson at the after-party for the Rolling Stones’ “Voodoo Lounge” Tour at the Hollywood Legion Hall. Oct. 19, 1994.Ron Galella/Ron Galella Collection/Getty Images 52 of 56Leonardo DiCaprio and Dennis Hopper hang out like old friends at a party at Club USA. April 2, 1994.Steve Eichner/Getty Images 53 of 56Marisa Tomei at a party for The Naked Angels Theatre Company. June 10, 1993.Ron Galella/Ron Galella Collection/Getty Images 54 of 56Kate Moss and Mark Wahlberg on Sept. 19, 1995.Barry King/WireImage/Getty Images 55 of 56"Cameron Diaz and I talk about this all the time," said Gwyneth Paltrow. “We’re like, ‘Thank God in the early ’90s there were [so few] paparazzi. Thank God.’ We cry in gratitude that no one was following us around and seeing what we were doing… I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house. That would never happen today.” Paltrow is pictured here with then-boyfriend Brad Pitt Oct. 29, 1995. Kevin Mazur Archive/WireImage/Getty Images 56 of 56Like this gallery?Share it:
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‘The Last Good Time’: 55 Vintage Photos From Early ’90s Hollywood View Gallery
Before there was a camera on every phone and a phone in every pocket, celebrities could still go out without being all but certain that their exploits would be recorded by somebody. This is why the 1990s were perhaps the last era in which Hollywood’s hot, young talent could go out, let loose, and feel more like the popular kid in school, rather than an alien being documented by the masses.
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Vintage Hollywood In 48 Photos
Hollywood’s Old Loves: Vintage Celebrity Couples That Time Almost Forgot
33 Photos From The Isle Of Wight Festival 1970 And The Other Wild Early Years
1 of 56Hollywood’s early 1990s power couple, Johnny Depp and Winona Ryder, attend photographer Herb Ritts’ birthday party. Sept. 18, 1990.Barry King/WireImage/Getty Images 2 of 56Keanu Reeves at the premiere for Bill & Ted’s Bogus Journey at the Hollywood Palladium on July 11, 1991.Ron Galella/Ron Galella Collection/Getty Images 3 of 56Mark Wahlberg and Leonardo DiCaprio, who became friends while filming The Basketball Diaries. Nov. 11, 1993.Ke.Mazur/WireImage/Getty Images 4 of 56Angeline Jolie and Peta Wilson hit the dance floor at the 1997 Cable Ace Awards.Twitter 5 of 56Before he was Tyrion Lannister, Peter Dinklage sang in a band called Whizzy, seen performing here circa the early 1990s.Twitter 6 of 56From left, Patrick Dempsey, Richard Grieco, Costas Mandylor, and Christian Slater pal around while celebrating the release of Grieco’s film, If Looks Could Kill, at the Roxbury Club on March 9, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 7 of 56Johnny Depp and Winona Ryder attend the Mermaids premiere one year into their relationship. Dec. 10, 1990.Barry King/WireImage/Getty Images 8 of 56Charlize Theron celebrating her 22nd birthday with Hollywood’s bright new shining star, Leonardo DiCaprio, who was smack-dab in the middle of Titanic superstardom. 1997.Randall Slavin 9 of 56Pauly Shore, Judy Tenuta, and Fabio squeeze some fun out of Shore’s HBO comedy special release party on Aug. 26, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 10 of 56Brooke Shields and Michael Jackson arrive at the 35th Annual Grammy Awards after-party at Jimmy’s Restaurant in Beverly Hills. Feb. 24, 1993.Steve Graniz/WireImage/Getty Images 11 of 56On the set of My Own Private Idaho, Keanu Reeves and co-star River Phoenix hang out while director Gus Van Sant snaps a photo. 1990.Twitter 12 of 56A young Leonardo DiCaprio and Johnny Depp attend the L.A. premiere for What’s Eating Gilbert Grape at the Paramount Theater on Dec. 12, 1993.Ron Galella, Ltd./Ron Galella Collection/Getty Images 13 of 56Patrick Dempsey at the premiere of If Looks Could Kill, starring Richard Grieco, at the Roxbury Club on March 9, 1991.Jim Smeal/Ron Galella Collection/Getty Images 14 of 56Winona Ryder and boyfriend Johnny Depp attend the premiere for The Silence of the Lambs in Century City on Feb. 1, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 15 of 56Keanu Reeves and My Own Private Idaho co-star and friend, River Phoenix. 1990.Twitter 16 of 56Richard Gere, Cindy Crawford, and famous paparazzi photographer Ron Gallela arrive at the 1991 Moving Picture Ball. The night’s event was a tribute to Martin Scorsese’s contributions to cinema. 1991.Frank Trapper/Corbis/Getty Images 17 of 56Will Smith and his The Fresh Prince of Bel Air castmates enjoy the party in celebration of the show’s 100th episode on Sept. 13, 1994.Chris Haston/NBCU Photo Bank/Getty Images 18 of 56Rob Lowe enjoys a cigarette outdoors in Los Angeles. Date unspecified.Barry King/WireImage/Getty Images 19 of 56Cameron Diaz and Milla Jovovich partying on the floor with some friends. 1995.Randall Slavin 20 of 56In the midst of DiCaprio Mania, magician David Blaine and actor Lukas Haas — who were both part of DiCaprio’s notorious “Pussy Posse,” lift their friend up by his legs. Nov. 2, 1995.Patrick McMullan/Patrick McMullan/Getty Images 21 of 56Johnny Depp and gonzo journalist Hunter S. Thompson became fast friends during preproduction for Fear and Loathing in Las Vegas. Here they are holding a reading of Thompson’s work at Depp’s Viper Room club. Sept. 7, 1996.Jeff Kravitz/FilmMagic, Inc./Getty Images 22 of 56"We were at the Viper Room but I met Benicio [Del Toro] a few years earlier when he had a small part in a movie I worked on, Swimming With Sharks," said photographer Randall Slavin. “Next to him is Joseph Kraemer, who has gone on to score films, including many of Chris McQuarrie’s.” 1996.Randall Slavin 23 of 56Richard Grieco and Christian Slater chill out and have a smoke during the If Looks Could Kill premiere at the Roxbury Club. March 9, 1991.Ron Galella/Ron Galella Collection/Getty Images 24 of 56Nicolas Cage and pal Charlie Sheen have a laugh at a party at Bar One Nightclub in West Hollywood. June 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 25 of 56Robert Downey Jr. during his tumultuous rollercoaster of a life in the early 1990s, pictured here at All Star Jam Night at the China Club in West Hollywood. June 26, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 26 of 56Keanu Reeves and David Bowie pose for a photo. 1992.Lester Cohen/Getty Images 27 of 56Leonardo DiCaprio and Brad Pitt pose for a photo at a party on Sept. 15, 1995.Patrick McMullan/Getty Images 28 of 56River Phoenix, K.D. Lang, and Liza Minnelli. Phoenix died two years later at Johnny Depp’s Viper Room club due to a drug overdose. Feb. 1, 1991.The LIFE Picture Collection/Getty Images 29 of 56Batman himself, Michael Keaton, with the Penguin, Danny DeVito, and Catwoman, Michelle Pfeiffer, attending the Batman Returns premiere in 1992.Twitter 30 of 56Kiefer Sutherland and Julia Roberts at Mann’s Chinese Theater for the Young Guns II premiere. July 30, 1990.Jim Smeal/Ron Galella Collection/Getty Images 31 of 56Nicolas Cage has a smoke and a drink with girlfriend Lisa Stothard at the premiere for the David Lynch-directed movie Wild at Heart. Aug. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 32 of 56Marilyn Manson with his new girlfriend Rose McGowan and Twiggy, Manson’s bassist and guitarist. 1997.Randall Slavin 33 of 56Actor Eddie Mills and Reese Witherspoon backstage at the Wiltern after a Counting Crows concert. Witherspoon was in the midst of blowing up, with the Mark Wahlberg-starring Fear having just been released. 1996.Randall Slavin 34 of 56Sting and his wife, Trudie Styler, heading into All Star Jam Night at the China Club. Feb. 12, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 35 of 56Sylvester Stallone, Demi Moore and husband Bruce Willis socializing at their shared business venture, Planet Hollywood. 1990.The LIFE Picture Collection/Getty Images 36 of 56Johnny Depp and his post-Winona girlfriend Kate Moss at the 42nd birthday party for Mickey Rourke — which Johnny Depp organized and paid for. Sept. 25, 1994.Richard Corkery/NY Daily News Archive/Getty Images 37 of 56Mickey Rourke and Johnny Depp at Rourke’s 42nd birthday party, thrown by Depp. Sept. 25, 1994.Lawrence Schwartzwald/Sygma/ Getty Images 38 of 56"[Filming Speed was hard for me to really be serious because he would look at me and I’d be like," said Sandra Bullock before making a swooning face. Keanu Reeves later said, “She obviously didn’t know that I had a crush on her, either.” The pair are pictured here at Planet Hollywood in 1994.The LIFE Picture Collection/Getty Images 39 of 56Cameron Diaz and Edward Norton met in 1998, shortly after he’d been nominated for an Academy Award. The romance didn’t last, and Norton went on to date Salma Hayek. Diaz and Norton are seen partying here in early 1999.KMazur/WireImage/Getty Images 40 of 56Gina Gershon and Rob Morrow attend the Trainspotting premiere after-party. July 15, 1996.Steve Eichner/WireImage/Getty Images 41 of 56Jude Law with actress Samantha Mathis. As photographer Randall Slavin later recalled, Mathis “rented this little house on Hillside, north of Franklin. We had this amazing summer there. When you’re in your 20s and you just all gather at this house — every day, every night.” 1995.Randall Slavin 42 of 56Liv Tyler and Joaquin Phoenix congratulate their friend, Matt Damon, on his success with Good Will Hunting. Dec. 4, 1997.Kevin Mazur Archive/WireImage/Getty Images 43 of 56Kate Moss and Oasis frontman Noel Gallagher, who later admitted, “By 1997 it had just gone berserk. I was doing loads of drugs and me and [bandmate and brother] Liam were just out of control.” Sept. 29, 1998.Dave Benett/Getty Images 44 of 56Arnold Schwarzenegger and Goldie Hawn during a party for Hawn’s Death Becomes Her at Planet Hollywood. July 13, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 45 of 56Brad Pitt and with John Lydon (otherwise known as Johnny Rotten) of the Sex Pistols, heading into a party hosted by David Bowie. Oct. 29, 1995.Ke.Mazur/WireImage/Getty Images 46 of 56Brooke Shields attends a party for Quincy Jones at the Roxbury in West Hollywood. July 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 47 of 56Nicolas Cage and friend Charlie Sheen stick together during a party for Guess Clothing hosted by Claudia Schiffer. Oct. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 48 of 56Corey Feldman attends a Planet Hollywood party in 1993.Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images 49 of 56Photographer Randall Slavin explained that Jeremy Davies (on Paul Rudd’s shoulders) just wrapped a guest spot on Buffy, and was super excited. “Then he got cut and was crushed.” Here they are at a Hole show, letting loose. 1996.Randall Slavin 50 of 56Glenn Close and Woody Harrelson at a performance of the play Brooklyn Laundry at the Coronet Theatre in West Hollywood. April 25, 1991.Ron Galella/Ron Galella Collection/Getty Images 51 of 56Judd Nelson at the after-party for the Rolling Stones’ “Voodoo Lounge” Tour at the Hollywood Legion Hall. Oct. 19, 1994.Ron Galella/Ron Galella Collection/Getty Images 52 of 56Leonardo DiCaprio and Dennis Hopper hang out like old friends at a party at Club USA. April 2, 1994.Steve Eichner/Getty Images 53 of 56Marisa Tomei at a party for The Naked Angels Theatre Company. June 10, 1993.Ron Galella/Ron Galella Collection/Getty Images 54 of 56Kate Moss and Mark Wahlberg on Sept. 19, 1995.Barry King/WireImage/Getty Images 55 of 56"Cameron Diaz and I talk about this all the time," said Gwyneth Paltrow. “We’re like, ‘Thank God in the early ’90s there were [so few] paparazzi. Thank God.’ We cry in gratitude that no one was following us around and seeing what we were doing… I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house. That would never happen today.” Paltrow is pictured here with then-boyfriend Brad Pitt Oct. 29, 1995. Kevin Mazur Archive/WireImage/Getty Images 56 of 56Like this gallery?Share it:
Share
Like this gallery?Share it:
Share
And if you liked this post, be sure to check out these popular posts:
Vintage Hollywood In 48 Photos
Hollywood’s Old Loves: Vintage Celebrity Couples That Time Almost Forgot
33 Photos From The Isle Of Wight Festival 1970 And The Other Wild Early Years
1 of 56Hollywood’s early 1990s power couple, Johnny Depp and Winona Ryder, attend photographer Herb Ritts’ birthday party. Sept. 18, 1990.Barry King/WireImage/Getty Images 2 of 56Keanu Reeves at the premiere for Bill & Ted’s Bogus Journey at the Hollywood Palladium on July 11, 1991.Ron Galella/Ron Galella Collection/Getty Images 3 of 56Mark Wahlberg and Leonardo DiCaprio, who became friends while filming The Basketball Diaries. Nov. 11, 1993.Ke.Mazur/WireImage/Getty Images 4 of 56Angeline Jolie and Peta Wilson hit the dance floor at the 1997 Cable Ace Awards.Twitter 5 of 56Before he was Tyrion Lannister, Peter Dinklage sang in a band called Whizzy, seen performing here circa the early 1990s.Twitter 6 of 56From left, Patrick Dempsey, Richard Grieco, Costas Mandylor, and Christian Slater pal around while celebrating the release of Grieco’s film, If Looks Could Kill, at the Roxbury Club on March 9, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 7 of 56Johnny Depp and Winona Ryder attend the Mermaids premiere one year into their relationship. Dec. 10, 1990.Barry King/WireImage/Getty Images 8 of 56Charlize Theron celebrating her 22nd birthday with Hollywood’s bright new shining star, Leonardo DiCaprio, who was smack-dab in the middle of Titanic superstardom. 1997.Randall Slavin 9 of 56Pauly Shore, Judy Tenuta, and Fabio squeeze some fun out of Shore’s HBO comedy special release party on Aug. 26, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 10 of 56Brooke Shields and Michael Jackson arrive at the 35th Annual Grammy Awards after-party at Jimmy’s Restaurant in Beverly Hills. Feb. 24, 1993.Steve Graniz/WireImage/Getty Images 11 of 56On the set of My Own Private Idaho, Keanu Reeves and co-star River Phoenix hang out while director Gus Van Sant snaps a photo. 1990.Twitter 12 of 56A young Leonardo DiCaprio and Johnny Depp attend the L.A. premiere for What’s Eating Gilbert Grape at the Paramount Theater on Dec. 12, 1993.Ron Galella, Ltd./Ron Galella Collection/Getty Images 13 of 56Patrick Dempsey at the premiere of If Looks Could Kill, starring Richard Grieco, at the Roxbury Club on March 9, 1991.Jim Smeal/Ron Galella Collection/Getty Images 14 of 56Winona Ryder and boyfriend Johnny Depp attend the premiere for The Silence of the Lambs in Century City on Feb. 1, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 15 of 56Keanu Reeves and My Own Private Idaho co-star and friend, River Phoenix. 1990.Twitter 16 of 56Richard Gere, Cindy Crawford, and famous paparazzi photographer Ron Gallela arrive at the 1991 Moving Picture Ball. The night’s event was a tribute to Martin Scorsese’s contributions to cinema. 1991.Frank Trapper/Corbis/Getty Images 17 of 56Will Smith and his The Fresh Prince of Bel Air castmates enjoy the party in celebration of the show’s 100th episode on Sept. 13, 1994.Chris Haston/NBCU Photo Bank/Getty Images 18 of 56Rob Lowe enjoys a cigarette outdoors in Los Angeles. Date unspecified.Barry King/WireImage/Getty Images 19 of 56Cameron Diaz and Milla Jovovich partying on the floor with some friends. 1995.Randall Slavin 20 of 56In the midst of DiCaprio Mania, magician David Blaine and actor Lukas Haas — who were both part of DiCaprio’s notorious “Pussy Posse,” lift their friend up by his legs. Nov. 2, 1995.Patrick McMullan/Patrick McMullan/Getty Images 21 of 56Johnny Depp and gonzo journalist Hunter S. Thompson became fast friends during preproduction for Fear and Loathing in Las Vegas. Here they are holding a reading of Thompson’s work at Depp’s Viper Room club. Sept. 7, 1996.Jeff Kravitz/FilmMagic, Inc./Getty Images 22 of 56"We were at the Viper Room but I met Benicio [Del Toro] a few years earlier when he had a small part in a movie I worked on, Swimming With Sharks," said photographer Randall Slavin. “Next to him is Joseph Kraemer, who has gone on to score films, including many of Chris McQuarrie’s.” 1996.Randall Slavin 23 of 56Richard Grieco and Christian Slater chill out and have a smoke during the If Looks Could Kill premiere at the Roxbury Club. March 9, 1991.Ron Galella/Ron Galella Collection/Getty Images 24 of 56Nicolas Cage and pal Charlie Sheen have a laugh at a party at Bar One Nightclub in West Hollywood. June 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 25 of 56Robert Downey Jr. during his tumultuous rollercoaster of a life in the early 1990s, pictured here at All Star Jam Night at the China Club in West Hollywood. June 26, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 26 of 56Keanu Reeves and David Bowie pose for a photo. 1992.Lester Cohen/Getty Images 27 of 56Leonardo DiCaprio and Brad Pitt pose for a photo at a party on Sept. 15, 1995.Patrick McMullan/Getty Images 28 of 56River Phoenix, K.D. Lang, and Liza Minnelli. Phoenix died two years later at Johnny Depp’s Viper Room club due to a drug overdose. Feb. 1, 1991.The LIFE Picture Collection/Getty Images 29 of 56Batman himself, Michael Keaton, with the Penguin, Danny DeVito, and Catwoman, Michelle Pfeiffer, attending the Batman Returns premiere in 1992.Twitter 30 of 56Kiefer Sutherland and Julia Roberts at Mann’s Chinese Theater for the Young Guns II premiere. July 30, 1990.Jim Smeal/Ron Galella Collection/Getty Images 31 of 56Nicolas Cage has a smoke and a drink with girlfriend Lisa Stothard at the premiere for the David Lynch-directed movie Wild at Heart. Aug. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 32 of 56Marilyn Manson with his new girlfriend Rose McGowan and Twiggy, Manson’s bassist and guitarist. 1997.Randall Slavin 33 of 56Actor Eddie Mills and Reese Witherspoon backstage at the Wiltern after a Counting Crows concert. Witherspoon was in the midst of blowing up, with the Mark Wahlberg-starring Fear having just been released. 1996.Randall Slavin 34 of 56Sting and his wife, Trudie Styler, heading into All Star Jam Night at the China Club. Feb. 12, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 35 of 56Sylvester Stallone, Demi Moore and husband Bruce Willis socializing at their shared business venture, Planet Hollywood. 1990.The LIFE Picture Collection/Getty Images 36 of 56Johnny Depp and his post-Winona girlfriend Kate Moss at the 42nd birthday party for Mickey Rourke — which Johnny Depp organized and paid for. Sept. 25, 1994.Richard Corkery/NY Daily News Archive/Getty Images 37 of 56Mickey Rourke and Johnny Depp at Rourke’s 42nd birthday party, thrown by Depp. Sept. 25, 1994.Lawrence Schwartzwald/Sygma/ Getty Images 38 of 56"[Filming Speed was hard for me to really be serious because he would look at me and I’d be like," said Sandra Bullock before making a swooning face. Keanu Reeves later said, “She obviously didn’t know that I had a crush on her, either.” The pair are pictured here at Planet Hollywood in 1994.The LIFE Picture Collection/Getty Images 39 of 56Cameron Diaz and Edward Norton met in 1998, shortly after he’d been nominated for an Academy Award. The romance didn’t last, and Norton went on to date Salma Hayek. Diaz and Norton are seen partying here in early 1999.KMazur/WireImage/Getty Images 40 of 56Gina Gershon and Rob Morrow attend the Trainspotting premiere after-party. July 15, 1996.Steve Eichner/WireImage/Getty Images 41 of 56Jude Law with actress Samantha Mathis. As photographer Randall Slavin later recalled, Mathis “rented this little house on Hillside, north of Franklin. We had this amazing summer there. When you’re in your 20s and you just all gather at this house — every day, every night.” 1995.Randall Slavin 42 of 56Liv Tyler and Joaquin Phoenix congratulate their friend, Matt Damon, on his success with Good Will Hunting. Dec. 4, 1997.Kevin Mazur Archive/WireImage/Getty Images 43 of 56Kate Moss and Oasis frontman Noel Gallagher, who later admitted, “By 1997 it had just gone berserk. I was doing loads of drugs and me and [bandmate and brother] Liam were just out of control.” Sept. 29, 1998.Dave Benett/Getty Images 44 of 56Arnold Schwarzenegger and Goldie Hawn during a party for Hawn’s Death Becomes Her at Planet Hollywood. July 13, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 45 of 56Brad Pitt and with John Lydon (otherwise known as Johnny Rotten) of the Sex Pistols, heading into a party hosted by David Bowie. Oct. 29, 1995.Ke.Mazur/WireImage/Getty Images 46 of 56Brooke Shields attends a party for Quincy Jones at the Roxbury in West Hollywood. July 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 47 of 56Nicolas Cage and friend Charlie Sheen stick together during a party for Guess Clothing hosted by Claudia Schiffer. Oct. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 48 of 56Corey Feldman attends a Planet Hollywood party in 1993.Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images 49 of 56Photographer Randall Slavin explained that Jeremy Davies (on Paul Rudd’s shoulders) just wrapped a guest spot on Buffy, and was super excited. “Then he got cut and was crushed.” Here they are at a Hole show, letting loose. 1996.Randall Slavin 50 of 56Glenn Close and Woody Harrelson at a performance of the play Brooklyn Laundry at the Coronet Theatre in West Hollywood. April 25, 1991.Ron Galella/Ron Galella Collection/Getty Images 51 of 56Judd Nelson at the after-party for the Rolling Stones’ “Voodoo Lounge” Tour at the Hollywood Legion Hall. Oct. 19, 1994.Ron Galella/Ron Galella Collection/Getty Images 52 of 56Leonardo DiCaprio and Dennis Hopper hang out like old friends at a party at Club USA. April 2, 1994.Steve Eichner/Getty Images 53 of 56Marisa Tomei at a party for The Naked Angels Theatre Company. June 10, 1993.Ron Galella/Ron Galella Collection/Getty Images 54 of 56Kate Moss and Mark Wahlberg on Sept. 19, 1995.Barry King/WireImage/Getty Images 55 of 56"Cameron Diaz and I talk about this all the time," said Gwyneth Paltrow. “We’re like, ‘Thank God in the early ’90s there were [so few] paparazzi. Thank God.’ We cry in gratitude that no one was following us around and seeing what we were doing… I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house. That would never happen today.” Paltrow is pictured here with then-boyfriend Brad Pitt Oct. 29, 1995. Kevin Mazur Archive/WireImage/Getty Images 56 of 56Like this gallery?Share it:
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1 of 56Hollywood’s early 1990s power couple, Johnny Depp and Winona Ryder, attend photographer Herb Ritts’ birthday party. Sept. 18, 1990.Barry King/WireImage/Getty Images 2 of 56Keanu Reeves at the premiere for Bill & Ted’s Bogus Journey at the Hollywood Palladium on July 11, 1991.Ron Galella/Ron Galella Collection/Getty Images 3 of 56Mark Wahlberg and Leonardo DiCaprio, who became friends while filming The Basketball Diaries. Nov. 11, 1993.Ke.Mazur/WireImage/Getty Images 4 of 56Angeline Jolie and Peta Wilson hit the dance floor at the 1997 Cable Ace Awards.Twitter 5 of 56Before he was Tyrion Lannister, Peter Dinklage sang in a band called Whizzy, seen performing here circa the early 1990s.Twitter 6 of 56From left, Patrick Dempsey, Richard Grieco, Costas Mandylor, and Christian Slater pal around while celebrating the release of Grieco’s film, If Looks Could Kill, at the Roxbury Club on March 9, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 7 of 56Johnny Depp and Winona Ryder attend the Mermaids premiere one year into their relationship. Dec. 10, 1990.Barry King/WireImage/Getty Images 8 of 56Charlize Theron celebrating her 22nd birthday with Hollywood’s bright new shining star, Leonardo DiCaprio, who was smack-dab in the middle of Titanic superstardom. 1997.Randall Slavin 9 of 56Pauly Shore, Judy Tenuta, and Fabio squeeze some fun out of Shore’s HBO comedy special release party on Aug. 26, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 10 of 56Brooke Shields and Michael Jackson arrive at the 35th Annual Grammy Awards after-party at Jimmy’s Restaurant in Beverly Hills. Feb. 24, 1993.Steve Graniz/WireImage/Getty Images 11 of 56On the set of My Own Private Idaho, Keanu Reeves and co-star River Phoenix hang out while director Gus Van Sant snaps a photo. 1990.Twitter 12 of 56A young Leonardo DiCaprio and Johnny Depp attend the L.A. premiere for What’s Eating Gilbert Grape at the Paramount Theater on Dec. 12, 1993.Ron Galella, Ltd./Ron Galella Collection/Getty Images 13 of 56Patrick Dempsey at the premiere of If Looks Could Kill, starring Richard Grieco, at the Roxbury Club on March 9, 1991.Jim Smeal/Ron Galella Collection/Getty Images 14 of 56Winona Ryder and boyfriend Johnny Depp attend the premiere for The Silence of the Lambs in Century City on Feb. 1, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images 15 of 56Keanu Reeves and My Own Private Idaho co-star and friend, River Phoenix. 1990.Twitter 16 of 56Richard Gere, Cindy Crawford, and famous paparazzi photographer Ron Gallela arrive at the 1991 Moving Picture Ball. The night’s event was a tribute to Martin Scorsese’s contributions to cinema. 1991.Frank Trapper/Corbis/Getty Images 17 of 56Will Smith and his The Fresh Prince of Bel Air castmates enjoy the party in celebration of the show’s 100th episode on Sept. 13, 1994.Chris Haston/NBCU Photo Bank/Getty Images 18 of 56Rob Lowe enjoys a cigarette outdoors in Los Angeles. Date unspecified.Barry King/WireImage/Getty Images 19 of 56Cameron Diaz and Milla Jovovich partying on the floor with some friends. 1995.Randall Slavin 20 of 56In the midst of DiCaprio Mania, magician David Blaine and actor Lukas Haas — who were both part of DiCaprio’s notorious “Pussy Posse,” lift their friend up by his legs. Nov. 2, 1995.Patrick McMullan/Patrick McMullan/Getty Images 21 of 56Johnny Depp and gonzo journalist Hunter S. Thompson became fast friends during preproduction for Fear and Loathing in Las Vegas. Here they are holding a reading of Thompson’s work at Depp’s Viper Room club. Sept. 7, 1996.Jeff Kravitz/FilmMagic, Inc./Getty Images 22 of 56"We were at the Viper Room but I met Benicio [Del Toro] a few years earlier when he had a small part in a movie I worked on, Swimming With Sharks," said photographer Randall Slavin. “Next to him is Joseph Kraemer, who has gone on to score films, including many of Chris McQuarrie’s.” 1996.Randall Slavin 23 of 56Richard Grieco and Christian Slater chill out and have a smoke during the If Looks Could Kill premiere at the Roxbury Club. March 9, 1991.Ron Galella/Ron Galella Collection/Getty Images 24 of 56Nicolas Cage and pal Charlie Sheen have a laugh at a party at Bar One Nightclub in West Hollywood. June 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 25 of 56Robert Downey Jr. during his tumultuous rollercoaster of a life in the early 1990s, pictured here at All Star Jam Night at the China Club in West Hollywood. June 26, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 26 of 56Keanu Reeves and David Bowie pose for a photo. 1992.Lester Cohen/Getty Images 27 of 56Leonardo DiCaprio and Brad Pitt pose for a photo at a party on Sept. 15, 1995.Patrick McMullan/Getty Images 28 of 56River Phoenix, K.D. Lang, and Liza Minnelli. Phoenix died two years later at Johnny Depp’s Viper Room club due to a drug overdose. Feb. 1, 1991.The LIFE Picture Collection/Getty Images 29 of 56Batman himself, Michael Keaton, with the Penguin, Danny DeVito, and Catwoman, Michelle Pfeiffer, attending the Batman Returns premiere in 1992.Twitter 30 of 56Kiefer Sutherland and Julia Roberts at Mann’s Chinese Theater for the Young Guns II premiere. July 30, 1990.Jim Smeal/Ron Galella Collection/Getty Images 31 of 56Nicolas Cage has a smoke and a drink with girlfriend Lisa Stothard at the premiere for the David Lynch-directed movie Wild at Heart. Aug. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 32 of 56Marilyn Manson with his new girlfriend Rose McGowan and Twiggy, Manson’s bassist and guitarist. 1997.Randall Slavin 33 of 56Actor Eddie Mills and Reese Witherspoon backstage at the Wiltern after a Counting Crows concert. Witherspoon was in the midst of blowing up, with the Mark Wahlberg-starring Fear having just been released. 1996.Randall Slavin 34 of 56Sting and his wife, Trudie Styler, heading into All Star Jam Night at the China Club. Feb. 12, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 35 of 56Sylvester Stallone, Demi Moore and husband Bruce Willis socializing at their shared business venture, Planet Hollywood. 1990.The LIFE Picture Collection/Getty Images 36 of 56Johnny Depp and his post-Winona girlfriend Kate Moss at the 42nd birthday party for Mickey Rourke — which Johnny Depp organized and paid for. Sept. 25, 1994.Richard Corkery/NY Daily News Archive/Getty Images 37 of 56Mickey Rourke and Johnny Depp at Rourke’s 42nd birthday party, thrown by Depp. Sept. 25, 1994.Lawrence Schwartzwald/Sygma/ Getty Images 38 of 56"[Filming Speed was hard for me to really be serious because he would look at me and I’d be like," said Sandra Bullock before making a swooning face. Keanu Reeves later said, “She obviously didn’t know that I had a crush on her, either.” The pair are pictured here at Planet Hollywood in 1994.The LIFE Picture Collection/Getty Images 39 of 56Cameron Diaz and Edward Norton met in 1998, shortly after he’d been nominated for an Academy Award. The romance didn’t last, and Norton went on to date Salma Hayek. Diaz and Norton are seen partying here in early 1999.KMazur/WireImage/Getty Images 40 of 56Gina Gershon and Rob Morrow attend the Trainspotting premiere after-party. July 15, 1996.Steve Eichner/WireImage/Getty Images 41 of 56Jude Law with actress Samantha Mathis. As photographer Randall Slavin later recalled, Mathis “rented this little house on Hillside, north of Franklin. We had this amazing summer there. When you’re in your 20s and you just all gather at this house — every day, every night.” 1995.Randall Slavin 42 of 56Liv Tyler and Joaquin Phoenix congratulate their friend, Matt Damon, on his success with Good Will Hunting. Dec. 4, 1997.Kevin Mazur Archive/WireImage/Getty Images 43 of 56Kate Moss and Oasis frontman Noel Gallagher, who later admitted, “By 1997 it had just gone berserk. I was doing loads of drugs and me and [bandmate and brother] Liam were just out of control.” Sept. 29, 1998.Dave Benett/Getty Images 44 of 56Arnold Schwarzenegger and Goldie Hawn during a party for Hawn’s Death Becomes Her at Planet Hollywood. July 13, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images 45 of 56Brad Pitt and with John Lydon (otherwise known as Johnny Rotten) of the Sex Pistols, heading into a party hosted by David Bowie. Oct. 29, 1995.Ke.Mazur/WireImage/Getty Images 46 of 56Brooke Shields attends a party for Quincy Jones at the Roxbury in West Hollywood. July 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 47 of 56Nicolas Cage and friend Charlie Sheen stick together during a party for Guess Clothing hosted by Claudia Schiffer. Oct. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images 48 of 56Corey Feldman attends a Planet Hollywood party in 1993.Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images 49 of 56Photographer Randall Slavin explained that Jeremy Davies (on Paul Rudd’s shoulders) just wrapped a guest spot on Buffy, and was super excited. “Then he got cut and was crushed.” Here they are at a Hole show, letting loose. 1996.Randall Slavin 50 of 56Glenn Close and Woody Harrelson at a performance of the play Brooklyn Laundry at the Coronet Theatre in West Hollywood. April 25, 1991.Ron Galella/Ron Galella Collection/Getty Images 51 of 56Judd Nelson at the after-party for the Rolling Stones’ “Voodoo Lounge” Tour at the Hollywood Legion Hall. Oct. 19, 1994.Ron Galella/Ron Galella Collection/Getty Images 52 of 56Leonardo DiCaprio and Dennis Hopper hang out like old friends at a party at Club USA. April 2, 1994.Steve Eichner/Getty Images 53 of 56Marisa Tomei at a party for The Naked Angels Theatre Company. June 10, 1993.Ron Galella/Ron Galella Collection/Getty Images 54 of 56Kate Moss and Mark Wahlberg on Sept. 19, 1995.Barry King/WireImage/Getty Images 55 of 56"Cameron Diaz and I talk about this all the time," said Gwyneth Paltrow. “We’re like, ‘Thank God in the early ’90s there were [so few] paparazzi. Thank God.’ We cry in gratitude that no one was following us around and seeing what we were doing… I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house. That would never happen today.” Paltrow is pictured here with then-boyfriend Brad Pitt Oct. 29, 1995. Kevin Mazur Archive/WireImage/Getty Images 56 of 56Like this gallery?Share it:
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1 of 56Hollywood’s early 1990s power couple, Johnny Depp and Winona Ryder, attend photographer Herb Ritts’ birthday party. Sept. 18, 1990.Barry King/WireImage/Getty Images
2 of 56Keanu Reeves at the premiere for Bill & Ted’s Bogus Journey at the Hollywood Palladium on July 11, 1991.Ron Galella/Ron Galella Collection/Getty Images
3 of 56Mark Wahlberg and Leonardo DiCaprio, who became friends while filming The Basketball Diaries. Nov. 11, 1993.Ke.Mazur/WireImage/Getty Images
4 of 56Angeline Jolie and Peta Wilson hit the dance floor at the 1997 Cable Ace Awards.Twitter
5 of 56Before he was Tyrion Lannister, Peter Dinklage sang in a band called Whizzy, seen performing here circa the early 1990s.Twitter
6 of 56From left, Patrick Dempsey, Richard Grieco, Costas Mandylor, and Christian Slater pal around while celebrating the release of Grieco’s film, If Looks Could Kill, at the Roxbury Club on March 9, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images
7 of 56Johnny Depp and Winona Ryder attend the Mermaids premiere one year into their relationship. Dec. 10, 1990.Barry King/WireImage/Getty Images
8 of 56Charlize Theron celebrating her 22nd birthday with Hollywood’s bright new shining star, Leonardo DiCaprio, who was smack-dab in the middle of Titanic superstardom. 1997.Randall Slavin
9 of 56Pauly Shore, Judy Tenuta, and Fabio squeeze some fun out of Shore’s HBO comedy special release party on Aug. 26, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images
10 of 56Brooke Shields and Michael Jackson arrive at the 35th Annual Grammy Awards after-party at Jimmy’s Restaurant in Beverly Hills. Feb. 24, 1993.Steve Graniz/WireImage/Getty Images
11 of 56On the set of My Own Private Idaho, Keanu Reeves and co-star River Phoenix hang out while director Gus Van Sant snaps a photo. 1990.Twitter
12 of 56A young Leonardo DiCaprio and Johnny Depp attend the L.A. premiere for What’s Eating Gilbert Grape at the Paramount Theater on Dec. 12, 1993.Ron Galella, Ltd./Ron Galella Collection/Getty Images
13 of 56Patrick Dempsey at the premiere of If Looks Could Kill, starring Richard Grieco, at the Roxbury Club on March 9, 1991.Jim Smeal/Ron Galella Collection/Getty Images
14 of 56Winona Ryder and boyfriend Johnny Depp attend the premiere for The Silence of the Lambs in Century City on Feb. 1, 1991.Ron Galella, Ltd./Ron Galella Collection/Getty Images
15 of 56Keanu Reeves and My Own Private Idaho co-star and friend, River Phoenix. 1990.Twitter
16 of 56Richard Gere, Cindy Crawford, and famous paparazzi photographer Ron Gallela arrive at the 1991 Moving Picture Ball. The night’s event was a tribute to Martin Scorsese’s contributions to cinema. 1991.Frank Trapper/Corbis/Getty Images
17 of 56Will Smith and his The Fresh Prince of Bel Air castmates enjoy the party in celebration of the show’s 100th episode on Sept. 13, 1994.Chris Haston/NBCU Photo Bank/Getty Images
18 of 56Rob Lowe enjoys a cigarette outdoors in Los Angeles. Date unspecified.Barry King/WireImage/Getty Images
19 of 56Cameron Diaz and Milla Jovovich partying on the floor with some friends. 1995.Randall Slavin
20 of 56In the midst of DiCaprio Mania, magician David Blaine and actor Lukas Haas — who were both part of DiCaprio’s notorious “Pussy Posse,” lift their friend up by his legs. Nov. 2, 1995.Patrick McMullan/Patrick McMullan/Getty Images
21 of 56Johnny Depp and gonzo journalist Hunter S. Thompson became fast friends during preproduction for Fear and Loathing in Las Vegas. Here they are holding a reading of Thompson’s work at Depp’s Viper Room club. Sept. 7, 1996.Jeff Kravitz/FilmMagic, Inc./Getty Images
22 of 56"We were at the Viper Room but I met Benicio [Del Toro] a few years earlier when he had a small part in a movie I worked on, Swimming With Sharks," said photographer Randall Slavin. “Next to him is Joseph Kraemer, who has gone on to score films, including many of Chris McQuarrie’s.” 1996.Randall Slavin
23 of 56Richard Grieco and Christian Slater chill out and have a smoke during the If Looks Could Kill premiere at the Roxbury Club. March 9, 1991.Ron Galella/Ron Galella Collection/Getty Images
24 of 56Nicolas Cage and pal Charlie Sheen have a laugh at a party at Bar One Nightclub in West Hollywood. June 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images
25 of 56Robert Downey Jr. during his tumultuous rollercoaster of a life in the early 1990s, pictured here at All Star Jam Night at the China Club in West Hollywood. June 26, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images
26 of 56Keanu Reeves and David Bowie pose for a photo. 1992.Lester Cohen/Getty Images
27 of 56Leonardo DiCaprio and Brad Pitt pose for a photo at a party on Sept. 15, 1995.Patrick McMullan/Getty Images
28 of 56River Phoenix, K.D. Lang, and Liza Minnelli. Phoenix died two years later at Johnny Depp’s Viper Room club due to a drug overdose. Feb. 1, 1991.The LIFE Picture Collection/Getty Images
29 of 56Batman himself, Michael Keaton, with the Penguin, Danny DeVito, and Catwoman, Michelle Pfeiffer, attending the Batman Returns premiere in 1992.Twitter
30 of 56Kiefer Sutherland and Julia Roberts at Mann’s Chinese Theater for the Young Guns II premiere. July 30, 1990.Jim Smeal/Ron Galella Collection/Getty Images
31 of 56Nicolas Cage has a smoke and a drink with girlfriend Lisa Stothard at the premiere for the David Lynch-directed movie Wild at Heart. Aug. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images
32 of 56Marilyn Manson with his new girlfriend Rose McGowan and Twiggy, Manson’s bassist and guitarist. 1997.Randall Slavin
33 of 56Actor Eddie Mills and Reese Witherspoon backstage at the Wiltern after a Counting Crows concert. Witherspoon was in the midst of blowing up, with the Mark Wahlberg-starring Fear having just been released. 1996.Randall Slavin
34 of 56Sting and his wife, Trudie Styler, heading into All Star Jam Night at the China Club. Feb. 12, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images
35 of 56Sylvester Stallone, Demi Moore and husband Bruce Willis socializing at their shared business venture, Planet Hollywood. 1990.The LIFE Picture Collection/Getty Images
36 of 56Johnny Depp and his post-Winona girlfriend Kate Moss at the 42nd birthday party for Mickey Rourke — which Johnny Depp organized and paid for. Sept. 25, 1994.Richard Corkery/NY Daily News Archive/Getty Images
37 of 56Mickey Rourke and Johnny Depp at Rourke’s 42nd birthday party, thrown by Depp. Sept. 25, 1994.Lawrence Schwartzwald/Sygma/ Getty Images
38 of 56"[Filming Speed was hard for me to really be serious because he would look at me and I’d be like," said Sandra Bullock before making a swooning face. Keanu Reeves later said, “She obviously didn’t know that I had a crush on her, either.” The pair are pictured here at Planet Hollywood in 1994.The LIFE Picture Collection/Getty Images
39 of 56Cameron Diaz and Edward Norton met in 1998, shortly after he’d been nominated for an Academy Award. The romance didn’t last, and Norton went on to date Salma Hayek. Diaz and Norton are seen partying here in early 1999.KMazur/WireImage/Getty Images
40 of 56Gina Gershon and Rob Morrow attend the Trainspotting premiere after-party. July 15, 1996.Steve Eichner/WireImage/Getty Images
41 of 56Jude Law with actress Samantha Mathis. As photographer Randall Slavin later recalled, Mathis “rented this little house on Hillside, north of Franklin. We had this amazing summer there. When you’re in your 20s and you just all gather at this house — every day, every night.” 1995.Randall Slavin
42 of 56Liv Tyler and Joaquin Phoenix congratulate their friend, Matt Damon, on his success with Good Will Hunting. Dec. 4, 1997.Kevin Mazur Archive/WireImage/Getty Images
43 of 56Kate Moss and Oasis frontman Noel Gallagher, who later admitted, “By 1997 it had just gone berserk. I was doing loads of drugs and me and [bandmate and brother] Liam were just out of control.” Sept. 29, 1998.Dave Benett/Getty Images
44 of 56Arnold Schwarzenegger and Goldie Hawn during a party for Hawn’s Death Becomes Her at Planet Hollywood. July 13, 1992.Ron Galella, Ltd./Ron Galella Collection/Getty Images
45 of 56Brad Pitt and with John Lydon (otherwise known as Johnny Rotten) of the Sex Pistols, heading into a party hosted by David Bowie. Oct. 29, 1995.Ke.Mazur/WireImage/Getty Images
46 of 56Brooke Shields attends a party for Quincy Jones at the Roxbury in West Hollywood. July 16, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images
47 of 56Nicolas Cage and friend Charlie Sheen stick together during a party for Guess Clothing hosted by Claudia Schiffer. Oct. 13, 1990.Ron Galella, Ltd./Ron Galella Collection/Getty Images
48 of 56Corey Feldman attends a Planet Hollywood party in 1993.Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images
49 of 56Photographer Randall Slavin explained that Jeremy Davies (on Paul Rudd’s shoulders) just wrapped a guest spot on Buffy, and was super excited. “Then he got cut and was crushed.” Here they are at a Hole show, letting loose. 1996.Randall Slavin
50 of 56Glenn Close and Woody Harrelson at a performance of the play Brooklyn Laundry at the Coronet Theatre in West Hollywood. April 25, 1991.Ron Galella/Ron Galella Collection/Getty Images
51 of 56Judd Nelson at the after-party for the Rolling Stones’ “Voodoo Lounge” Tour at the Hollywood Legion Hall. Oct. 19, 1994.Ron Galella/Ron Galella Collection/Getty Images
52 of 56Leonardo DiCaprio and Dennis Hopper hang out like old friends at a party at Club USA. April 2, 1994.Steve Eichner/Getty Images
53 of 56Marisa Tomei at a party for The Naked Angels Theatre Company. June 10, 1993.Ron Galella/Ron Galella Collection/Getty Images
54 of 56Kate Moss and Mark Wahlberg on Sept. 19, 1995.Barry King/WireImage/Getty Images
55 of 56"Cameron Diaz and I talk about this all the time," said Gwyneth Paltrow. “We’re like, ‘Thank God in the early ’90s there were [so few] paparazzi. Thank God.’ We cry in gratitude that no one was following us around and seeing what we were doing… I remember when Brad Pitt and I broke up, it was on the cover of the New York Post and there was no one outside my house. That would never happen today.” Paltrow is pictured here with then-boyfriend Brad Pitt Oct. 29, 1995. Kevin Mazur Archive/WireImage/Getty Images
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‘The Last Good Time’: 55 Vintage Photos From Early ’90s Hollywood View Gallery
‘The Last Good Time’: 55 Vintage Photos From Early ’90s Hollywood View Gallery
‘The Last Good Time’: 55 Vintage Photos From Early ’90s Hollywood View Gallery
‘The Last Good Time’: 55 Vintage Photos From Early ’90s Hollywood View Gallery
‘The Last Good Time’: 55 Vintage Photos From Early ’90s Hollywood
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Without such relative privacy, how else could Leonardo DiCaprio casually attend Charlize Theron’s 22nd birthday party at Sunset Boulevard’s infamous Chateau Marmont at the height of the global Titanic craze? How else could Johnny Depp buy a club, the Viper Room, and host all manner of debaucherous shenanigans inside?
And though this era was the last gasp of this kind of privacy, enough cameras were present to give us a glimpse of what Hollywood was like for the up-and-coming stars that ruled the first half of the ’90s.
Discover more about this wild time below and travel back in time via the gallery above to revisit a world long gone by — yet one that will, nonetheless, live forever.
The Viper Room And The Wild Nights Of Early ’90s Hollywood
Before Johnny Depp bought the place in 1993 and called it the Viper Room, 8852 Sunset Boulevard’s Melody Room once served as a meeting place for the likes of infamous mobster Bugsy Siegel. But as soon as Depp took it over, it became the hot spot for young Hollywood. According to Hollywood Interrupted, no other spot on the strip was a hotter meeting place for young actors in the early 1990s.
In fact, New York Times bestselling author Mark Ebner said the audience was commonly far more famous than the rockers performing on the club’s stage. Actress Samantha Mathis of Little Women and American Psycho fame — also the girlfriend of actor River Phoenix — as well as actor Richmond Arquette (brother of David, Rosanna, and Patricia), who often tended bar there, remembered it fondly.
“You knew that on Thursday night you’d put on the dress and the heels and the red lipstick,” said Mathis. “And there were the Pussycat Dolls, and you’d see them dance around…[they] are sort of a burlesque, 1940s-style, all-girl show — they do these dances wearing bowler hats and underwear.”
“It was great,” said Arquette. “Christina Applegate was one of them for a while, and they actually danced recently at Leonardo DiCaprio’s birthday party… The first time I ever set foot in the Viper Room, Johnny Cash was playing.”
Denny Keeler/Contributor/Getty ImagesKeanu Reeves stands outside The Viper Room after performing with his band, Dogstar.
Viper Room talent booker Stacey Grenrock recalled transforming the club into a different theme every Monday. One week there would be mimes and people dressed as snowmen running around, while the following week would have a man dressed up as a gorilla barreling through the room.
“I can’t think of a cooler place to play in L.A. than the Viper Room,” said Nancy Sinatra. “If my dad were still performing, he’d want to play an after-hours show there.”
And though Old Blue Eyes may have fancied a show at the Viper Room, it was indeed the generation that ruled early ’90s Hollywood who made it their own. And it was here and other L.A. hotspots that these newly famous young actors cut loose — without fear of seeing their antics online the next day.
No Cameras, No Problem
Photographer Randall Slavin remembers the early ’90s era as the dying breath of freedom for those with any semblance of fame.
“Hollywood in the nineties was the last good time,” he said. “You went out, and things would happen, and no one would know about it, which fostered an incredible sense of fun and party atmosphere. It was a different era, because people could let go and no one would take their pictures.”
Randall SlavinJennifer Aniston had just become a break-out star on Friends when she started dating Counting Crows frontman Adam Duritz.
Slavin recalls, for example, when Counting Crows frontman Adam Duritz started dating Jennifer Aniston in 1995.
“Friends had just exploded and was massive, and Adam was in the biggest band in the country and his record was blowing up, so they were the biggest power couple,” said Slavin. “We would all sit on the back patio until the wee hours of the morning, taking about how everyone’s going to change the world and make great art.”
“It was a very fertile, creative, wild time,” said Duritz. “We all worked feverishly trying to make something of our lives and then went out every night and lost our minds. Crazy, wonderful time to be a young idiot in Hollywood.”
But, sometimes, the idiocy went from fun to dangerous.
Drugs, Alcohol, And Innocence Lost
With so many stars and parties, drugs were always going to be around.
“It’s amazing how many people I see on TV now who used to be standing around my kitchen doing lines at 3 in the morning,” author Bret Easton Ellis told The Hollywood Reporter of his wild ’90s days. “Peter Dinklage, Mario Batali, Candace Bushnell… so many greats passed through that cokey den of inequity.”
Johnny Depp, Hunter S. Thompson, and John Cusack arrive at the Viper Room in 1996.
Unfortunately, all good things inevitably come to an end, and even young Hollywood has to eventually reckon with that loss of innocence when the party must end. For Viper Room regulars and thus so many of early ’90s Hollywood’s in-crowd, that moment was encapsulated by the untimely drug overdose of 23-year-old star-in-the-making River Phoenix in the early morning hours of Oct. 31, 1993.
Johnny Depp, Hunter S. Thompson, and John Cusack arrive at the Viper Room in 1996.
On the night of Oct. 30, Phoenix came to the Viper Room to play a show with his band (which included Depp and Flea from the Red Hot Chili Peppers), but he was clearly not in a good way. He’d been on one of his regular drug binges — which he had down to a routine of coke or intravenous cocaine followed by heroin — and, in the words of friend Bob Forrest, looked like “a boxer who had taken one too many head-shots during a fifteen-round bout.”
Phoenix only consumed more cocaine once inside the Viper Room and ultimately found his way out to the sidewalk, where he started convulsing as Mathis screamed in horror. His younger brother, Joaquin, called 911, but it was too late. He was taken to the hospital and promptly declared dead.
“The first night I was ever there, I was with River,” Mathis later recalled. “For reasons I don’t need to explain, it was ultimately not a joyous experience, and I think it was almost a year before I went back.”
Michael Ochs Archives/Getty ImagesThe exterior of The Viper Room on the day after the death of River Phoenix. Fans have left flowers, candles, and notes at the spot where he collapsed.
After Phoenix’s death, the wild days of the Viper Room and its regulars were never quite the same.
“I stepped in right after the River Phoenix incident,” said Viper Room employee Kimberly Toth. “It was a very awkward situation, and that’s when it became very touristy — there were a lot of out-of-town people with cameras.”
Nevertheless, though these heady days were dangerous and even fatal for some, plenty of other young stars made it through the early ’90s just fine. In fact, they had the time of their lives. And thanks to photos like those in the gallery above, we can peek in on their party-of-a-lifetime.
After traveling back in time to explore the early 1990s nightlife of young Hollywood stars in 55 mesmerizing photos, take a look at 66 revealing photos of celebrities before they were famous. Then, check out vintage Hollywood in 48 photos.
