The House Bunny
He played himself in this 2008 comedy starring Anna Faris as a former Playboy Bunny, making a cameo with girlfriends Holly Madison, Kendra Wilkinson-Baskett and Bridget Marquardt.
Entourage
He and his girlfriends appeared on a 2005 episode of Entourage, which sees Vince and his friends attend a party at the Playboy Mansion. After some drama with...Drama, Hef has longtime partygoer Pauly Shore tossed out.
Sex and the City
On a 2000 episode of Sex and the City, Samantha Jones also gets herself kicked out of a Playboy Mansion party when she falsely accuses one of Hef's girlfriends of stealing her purse.
The Simpsons
Hef voiced himself on a 1993 episode of the FOX animated series.
Curb Your Enthusiasm
Hef appeared on a 2005 episode of Larry David's HBO series.
Beverly Hills Cop II
Eddie Murphy's Axel Foley is super excited to meet Hef in the 1987 action movie.