The old adage that sex sells has been proven time and time again in entertainment, from movies to music. However, in spite of misogyny running rampant throughout a multitude of genres, cultures and societies, hip-hop has been tagged with the label multiple times throughout the years. The culture has lived up to it in terms of the music, visuals and figures that hip-hop celebrates as status symbols, with publishing icon, Playboy founder and lifestyle maven Hugh Hefner being among.

Playboy magazine was founded in 1953, after Hefner quit his job as a copywriter at Esquire to launch the publication, which was an instant success. The mag quickly becoming one of America's most beloved, and polarizing, brands in publishing. Far from a mere nude mag, Playboy and Hefner also made it their business to broach controversial topics revolving around sexuality, race, religion, gender and other facets of society. Hefner is also credited with helping to jumpstart the career of comedian/activist Dick Gregory, and publishing interviews with civil rights leaders Malcolm X and Martin Luther King prior to their deaths.

However, Hugh Hefner's reputation as a bachelor and ladies man is the one that precedes him the most and made him a hero to a multitude of rap artists who dreamed to mirror his lifestyle prior to reaching their own stardom. Known for paying homage, rappers began to show their respect to Hefner by bigging him up in their rap lyrics, a bond that has been reciprocated, with legends like Snoop Dogg and Uncle Luke being just a few of the rappers to have had the pleasure of visiting the Playboy Mansion on Hefner's behalf.

Unfortunately, Hugh Hefner, 91, passed away Wednesday night (Sept. 27) at his home, the Playboy Mansion, in the Holmby Hills area of Los Angeles. Hefner's death rocked the hip-hop world, with a overwhelming amounts of artists and fans alike paying their respects to the legacy he left behind.

To commemorate the life, times and influence of Hugh Hefner, XXL compiled 20 noteworthy rap lyrics paying homage to the greatest playboy of them all. R.I.P.

  • "Drunk Dialing"

    Wiz Khalifa and Curren$y

    "You never know what will happen, spontaneous action/In the city of the Mardi Gras parades and gun clappin, quarterbacking/Not the center but I'm snapping bongs/Shorty don't be smoking like that she grown/Leon Phelps, Hugh Hef grotto flow/Boogie nights at the roxbury, Which way should we go huh?" - Curren$y

  • "Pretty Boy Remix"

    Lil B

    "Young BasedGod hit that bitch with that long dick/Work it like a pro, break a bitch ’cause I'm nasty/Brrrang thang thang got bitches Hugh Hefner/Black Hugh Hefner, hoodie with that sweatshirt"

  • "Girlfriend"

    Nicki Minaj

    "Ayo! Where my BFF/Where my Playboy bunny, where dat nigga Hugh Hef/When we pull off at da light, why everything else get left/Why dey screwin' up dey face, why dey lookin' a hot mess"

  • "OMG"

    Vic Mensa Featuring Pusha T and Pharrell Williams

    "Vic in Chicago, it's Hugh Hef at the grotto/Brazilian model, she mean mugging like Frida Kahlo/Drinking a horchata with an Alicia Machado/Bitch, I'm the ticket, you just hit the lotto" - Vic Mensa

  • "Poltergeist"

    Roc Marciano

    "Your milf kneeled up in the Vanderbilt, I killed it on the quilt/My wrist look chillt, ugh/Sip the nectar, shit is extra/The M emblem, the reflector, the beast squeeze the milli or the Winchester/As a gesture, my view is that of Hugh Hefner/I've yet to find a smoother texture in a pimp's dresser"

  • "Amnesia"

    Kevin Gates Featuring Doe B

    "I done fucked so many hoes I can't keep count no more/Will somebody tell Hugh Hefner he ain't got shit on Doe?/My neck on freeze, my wrist on glow/I'm high as fuck, I'm sitting low/Want your ho, come get your ho/I got her walking pigeon-toed" - Doe B

  • "Rewind"

    Lil Wayne and Juelz Santana

    "I do better, who better? You, never/Abuse cheddar, Playboy, Hugh Hefner/The two next up my dick yes uh/I buy a car just because I like the smell of new leather" - Juelz Santana

  • "Open Fire"

    Erick Sermon Featuring Keith Murray and Redman

    "The funk dwella in your cella, no one's wetta/Pull more Playboy bitches than Hugh Hefner/I played you wit my nasal style I'm able/To rock two turntables for old sake like Sweet Sable" - Redman

  • "THOT"

    Uncle Murda Featuring Young M.A and Dios Moreno

    "You know I'm tellin' the truth, I'm sippin' that Henny/She ain't call me Murda, let her call me Lenny/Wifey material, she not it/Can't believe I had my kids around that thot bitch/Gotta do better, should've knew better/Now I got a bunch've broads like Hugh Hefner" - Uncle Murda

  • "Hustler's Ambition"

    50 Cent

    "Them hollow tips bent me up, but I'm back in shape/Pour Cristal in the blender, make a protein shake/I'm like the East Coast No. 1 playboy, B/Hugh Hefner'll tell you he ain't got shit on me/The feds watch me, icey, they can't stop me/Racist, pointing at me, 'Look at Niggaraci'"

  • "Let My Niggas Live"

    Wu Tang Clan Featuring Nas

    "I been on boats, nut down throats, pee on bitches who famous/Pretty dick, puttin' stitches in they anus/I'm the animal that Hugh Hefner created/The only nigga Sade dated, the most hated, Nas, nigga" - Nas

  • "The Watcher 2"

    JAY-Z Featuring Dr. Dre, Rakim and Truth Hurts

    "You can't disrespect us, ’cause you got a little check cut/You was suckin' ’em so long, fuckin' your little neck up/Now you too big for your britches, you got a few little bitches/You think you Hugh Hefner, you just ridiculous" - JAY-Z

  • "Make It Go Right"

    Childish Gambino Featuring Kilo Kish

    "No need, don't explain to me, love/’Cause I know how you deal, but I could see us/In a different way, don't play me ’cause we're not the same/Sign on, sees your screen name and misbehave/So you're a playboy, you think you're Hef, kid?/Hoppin' round town with the bunnies when" - Kilo Kish

  • "Gifted"

    French Montana Featuring The Weeknd

    "This that Tiger Woods on his last swing/This that Jimi Hendrix on his last string/This that Larry Davis on his last bang/You can call me Hugh Hefner on his last fling" - French Montana

  • "My X"

    Rae Sremmurd

    "My ex-bitch, must have been defective/But my new bitch, look like Cinderella/She a dime bitch, ain't too much you can tell her/Upgrade everything, new whip, new bitch, new bezel/Got the Lam, chopped, it ain't nothin', I'm the real Hugh Hefner/And you didn't work out, that's cool ’cause my new bitch better" - Slim Jxmmi

  • "Hannah Montana (Twerk Remix)"


    "No Lil Jon you ain't on my level/Snow bunny like I'm Hugh Hefner/Running my sack up like Fletcher/You niggas to slow, need to catch up/My wrist so sick, got a virus/Birds be singing like Maya/Stop drop and roll like a fire/Drop it low like Miley Cyrus" - Offset

  • "God Bless Amerika"

    Lil Wayne

    "Ain’t that a bitch? I’m just a nut tryna bust a nut, in a nut shell/Used to say fuck the police, now I say fuck jail/Same shit, different air freshener/I don’t play, boy, I ain’t Hugh Hefner/Tryna be a step ahead, but a few feet behind/Two fingers to my head, pop! Peace of mind"

  • "Gone to the Moon"


    "Yeah, I smoke a box of blunts for breakfast/Ay, and I woke up like Hugh Hefner, ay/I had to switch her out my old phone/Ay, and I just got back from Tokyo, ay"

  • "Right Now & Later On"

    Fabolous Featuring Timbaland

    "It's the hoodrat Hugh Hefner, that bend dimes, too/The five plus one, sittin' on 10 times two/Shorty when I'm through..../I'm a know if you nice on the mic and if your friend rhyme, too/It's so funny how I suit the women/They know I'm still spendin' show money from "'Superwoman'" - Fabolous

  • "Coochie"


    "I stay away from the A-I-D/Pack condoms like guns ’cause thats the way I be/One love to the late great Eazy-E/Larry Flynt, Hugh Hefner and Ron Jeremy/Huah! I get pussy you know how I do/Call the crib last four numbers, 10-80-two" - Akinyele

More From XXL