HOLMBY HILLS, CA - MAY 09: Hugh Hefner attends Playboy's 2013 Playmate Of The Year luncheon honoring Raquel Pomplun at The Playboy Mansion on May 9, 2013 in Holmby Hills, California. (Photo by Charley Gallay/Getty Images for Playboy)
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Hugh Hefner and his role in civil rights
Don Lemon Tonight
Presidential historian Douglas Brinkley shares his memories of Playboy founder Hugh Hefner who died at the age of 91.
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HOLMBY HILLS, CA - MAY 09: Hugh Hefner attends Playboy's 2013 Playmate Of The Year luncheon honoring Raquel Pomplun at The Playboy Mansion on May 9, 2013 in Holmby Hills, California. (Photo by Charley Gallay/Getty Images for Playboy)
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Hugh Hefner and his role in civil rights
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LOS ANGELES, CA - JANUARY 16: Hugh Hefner poses at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
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LOS ANGELES, CA - JANUARY 16: Hugh Hefner poses at Playboy's 60th Anniversary special event on January 16, 2014 in Los Angeles, California. (Photo by Charley Gallay/Getty Images for Playboy)
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MUNICH, GERMANY - JANUARY 25: Playboy bunnies arrive for the DLD Starnight at Haus der Kunst on January 25, 2010 in Munich, Germany. (Photo by Johannes Simon/Getty Images for Hubert Burda Media)
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