Hugh Hefner Movies

Directed by Kevin Burns, this documentary from Playboy Home Video examines the oftentimes tense relationship between sex, women, and popular...

The Simpsons 20th Anniversary Special – In 3-D! On Ice! is a documentary special that examined the "cultural phenomenon" of the American...

Pamela Anderson was roasted by Courtney Love, Adam Carolla, Bea Arthur, Nick DiPaolo, Greg Giraldo, Elon Gold, Eddie Griffin, Lady Bunny, Lisa...

A look at the forces that shaped Pre-Code Hollywood and brought about the strict enforcement of the Hays Code in 1934.

The history of Playboy magazine as told by Hugh Hefner.

It is a sex education film of sorts dedicated to all forms of human sexuality.

What do Marilyn Monroe, Suzanne Somers, Pamela Anderson, Anna Nicole Smith, and Carmen Electra all have in common? Their show business careers were...

Elizabeth Hurley hosts a one hour documentary on the history of the James Bond film series to tie in with the seventeenth Bond film, GoldenEye.

This third installment in Playboy’s seductive series will captive your imagination with a collection of all-new tales guaranteed to please. Sex...

The world's greatest pin-up model and cult icon, Bettie Page, recounts the true story of how her free expression overcame government witch-hunts to...

A look back at the people, events, music, and trends of the 1970s.

A "tribute" to comedian Tommy Chong, given to him by many of his fellow comedians.

Eight erotic vignettes with Christmas themes involving Playboy Playmates.

A documentary on the famous Los Angeles street.

Despite decades of opposition from the right, and recent personal setbacks, Gloria Steinem remains one of the most outspoken and visible symbols of...

The life and times of famous Jack Nicholson include his 30-years relationship with Anjelica Houston and find out his sister is his real mother.

Playboy magazine darling (and one-time playmate of Hugh Hefner) Barbi Benton is Naughty Cheerleader Lynne Keefe, a small-town, small-brained babe who...

The Comedy Central Roasts are a series of celebrity roast specials which air on the Comedy Central cable network. This one is for Hugh Hefner.

The coffee's not the only thing that's hot and steamy in Playboy's Women of Starbucks. Ten beautiful baristas come out from behind the counter to...

Playboy brings you arousing fantasies that will push the boundaries of your imagination. Witness every searing moment as daring sexual fantasies are...