How Hugh Hefner leveraged his playboy lifestyle in advertising: booze, smoking and rock'n'roll
Hugh Hefner, late on Wednesday night, passed away in his home at the age of 91, leaving his family and the media, rifling through his heritage as cultural giant for around half a century.

Hugh Hefner supports top brands
While paying his respects, Playboy chief creative officer Cooper Hefner credited his father with supporting free speech and the civil rights movements as his built his media empire, but it is little known that in later life, Hefner indulged in a few prominent ads.
His recognisable loungewear and desirable playboy lifestyle helped connect with audiences with the desired level of humor. Across his body of work, he seemingly supported drinks brands and a rock and roll game; somewhat true to brand, here they are.
Bavaria (2011) Agency: Selmore
Operating as more as a behind-the-scenes, the somewhat telling ad shows that sometimes Hefner prefers the company of men his own age, and to that end, has a purpose-built old man pub that serves up Bavaria beer.
Guitar Hero 5 (2009) Agency: Crispin Porter + Bogusky Santa Monica and HSI
Few people sum up the rock and roll aspiration as much as Hugh Hefner, as such he appeared in a surprising riff on Tom Cruise's Risky Business air guitar gag for Guitar Hero.
Stolichnaya Vodka (2010) Agency: Ogilvy & Mather
Hefner, clearly a fan of a stiff drink like vodka, lent his talents to Stoli where he played two different versions of himself, the playboy and the businessman.
Tanqueray Gin (2002) Agency: Thompson New York
Another drink ad, Hefner knew what he liked. Russian vodka was among these. This campaign ran as print only and helped introduce the brand to the American market.

Hefner's Pipe
Worthy of a mention is Hefner's pipe... potential playboys could get a grip of their own for the reasonable price of $15. It's worth noting that the dapper gentleman below is not the Hef. In fact it is remarkably hard to find him in any adverts before the turn of the millennium – even for Playboy.

Additionally, across film and TV, Hefner is credited as playing himself in Curb Your Enthusiasm, Entourage, Sex and the City, Family Guy, The Simpsons, Roseanne and more.