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Justin Timberlake & Hugh Hefner
Following the death of Hugh Hefner, who passed away of natural causes at 91 at the Playboy Mansion, Billboard looks back on some of his most iconic visits with a slew of music’s biggest names. Here, Hugh Hefner and Justin Timberlake pose surrounded by Hefner’s girlfriends at the 2003 Teen People and Universal Records Party honoring him at the Ivar Night Club on Jan. 13, 2003 in Hollywood, Calif.
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Madonna & Hugh Hefner
Madonna and Hugh Hefner photographed Madonna’s “Music” Launch Party Hosted by Warner Bros Records and US Weekly on Sept. 19, 2000.
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Gene Simmons & Hugh Hefner
Hugh Hefner with Gene Simmons of Kiss and Playboy Bunnies At The Playboy Expo ’99 & Playmate Reunion Held At The Pacific Design Center.
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Cher & Hugh Hefner
Cher and Hugh Hefner attend the TCM Classic Film Festival Vanity Fair after party held at Kress on April 22, 2010 in Hollywood, Calif.
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Lil’ Kim & Hugh Hefner
Hugh Hefner, Lil’ Kim and Hefner’s girlfriends greet each other at the Warner Music Group and Entertainment Weekly post-Grammy party.
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Smokey Robinson & Hugh Hefner
Smokey Robinson greets Hugh Hefner after he arrives at the Barnstable Brown Derby party in Louisville on May 2, 2008.
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Marilyn Manson & Hugh Hefner
Hugh Hefner poses with Marilyn Manson and playboy playmate at the Henry Fonda Theater on Nov. 2, 2002 in Los Angeles.
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Will Smith, Hugh Hefner, Karyn Parsons & Alfonso Ribeiro
Will Smith, Hugh Hefner, Karyn Parsons, and Alfonso Ribeiro photographed during “Fresh Prince After Dark” on Nov. 08, 1993.
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Snoop Dogg & Hugh Hefner
Hugh Hefner and Snoop Dogg attend Spike TV’s 2nd Annual “Guys Choice” Awards at Sony Studios on May 30, 2008 in Culver City, Calif.
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Kanye West, Hugh Hefner & Kendra Wilkinson
Kanye West, Hugh Hefner and Kendra Wilkinson pose during Game Three of the 2008 NBA Finals between the Boston Celtics and the Los Angeles Lakers on June 10, 2008 at Staples Center in Los Angeles.
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Busta Ryhmes & Hugh Hefner
Hugh Hefner and Busta Ryhmes during The Official Launch Party For Spike TV At The Playboy Mansion – Inside at The Playboy Mansion in Bel Air, Calif.
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Ice T, Kylie Baxn & Hugh Hefner
Ice T, Kylie Baxn and Hugh Hefner photographed in New York on Sept. 29, 2001.
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Ashanti, Hugh Hefner & Pamela Anderson
Ashanti, Hugh Hefner and Pamela Anderson photographed at Playboy’s 50th Anniversary Celebration in New York City in 2003.
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Diana Ross & Hugh Hefner
Diana Ross and Hugh Hefner are seen inside at the 10th Annual Safari Brunch on Oct. 16, 2004 at the Playboy Mansion in Beverly Hills, Calif.
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Common & Hugh Hefner
Common and Hugh Hefner photographed at the 9th Annual Playboys Super Saturday Night Party on Feb. 2, 2008.
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Rod Stewart & Hugh Hefner
Rod Stewart poses with Hugh Hefner at The Pharmacy on Oct. 9, 2002 in Hollywood, Calif.
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Hugh Hefner, James Moody & Al Jarreau
Hugh Hefner poses with jazz musicians James Moody (L) and Al Jarreau during the announcement of the ‘Silver’ 25th Anniversary Playboy Jazz Festival Concert at the Playboy Mansion on Feb. 26, 2003 in Hollywood, Calif.