Hef introduces the 1959 American comedy classic.

Hef introduces the ultimate Christmas classic.

In honor of the late Frank Sinatra, Playboy.com counts down the coolest people of the last 70 years.

Relive Hef's sexy summer bash with Playmates in lingerie and lace at the world's ultimate pajama party.

The original gonzo journalist salutes Hef and worries that old communist conspiracy theories are being repackaged as the War on Terrorism—from the January 2004 issue.

Hef answered dozens of questions from fans following the premiere of NBC's The Playboy Club. See his answers here!

Watch a sexy video recap of Playmates and other poolside partiers!

Watch Hef's Runaway Bride television special tonight at 10/9 p.m. CT. on Lifetime and get the real story behind Hef and Crystal's emotional June break-up.

The skies were never friendlier than when Hugh Hefner took flight in his legendary jet.

See sexy pics from Miss November 2010 Shera Bechard's Playmate pictorial.

1926 Hugh Marston Hefner is born in Chicago on April 9 to Methodist parents Glenn and Grace Hefner. Ironically, Hef’s a direct descendent of Massachusetts Puritan patriarchs William Bradford and John Winthrop. 1940-1944 Hugh attends Steinmetz High on the West Side of Chicago, where he founds a school paper, draws cartoons and serves as president [...]

1980 Hef champions the reconstruction of the Hollywood sign and is honored with a star on the Hollywood Walk of Fame. 1981 Hef and 1982 Playmate of the Year Shannon Tweed become an item. 1981 Freelancer Cameron Crowe goes undercover for his September Playboy piece “Fast Times at Ridgemont High,” which was to become a [...]

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1960 Hef opens the first Playboy Club at 116 E. Walton in Chicago on February 29. 1961 At Hef’s invitation, comic Dick Gregory performs at the Chicago Playboy Club in January, becoming the first black performer to break the color barrier in a mainstream nightclub. 1962 Little Annie Fanny, a collaboration between Hef and cartoonists [...]

1971 Playboy Enterprises buys the Playboy Mansion West in the Holmby Hills district of Los Angeles, which becomes Hef’s new home. Take a 3-D tour of the Playboy Mansion» 1971 Playboy goes public. The first Playboy Enterprises-incorporated stock certificate is illustrated with a reclining nude Playmate. 1971 Hef meets Bunny-in-training and future Miss December Karen [...]

Who is the woman behind the man? Get to know Crystal Harris.

Going to Hef and Crystal's nuptials? The invitations -- about 300 of them -- are in the mail.

A candid conversation with Playboy's editor-publisher from the January 1974 20th anniversary issue.

Hefner's Sixties empire comes alive this fall on NBC with The Playboy Club.

Where were you when Hef was changing the world? Read the ultimate timeline of his life.

Take a peek at photos and videos from Hef's trip to London for the new Playboy Club opening.

Get to know the man behind the Playboy empire in exclusive videos, interviews and photos!

1951 In January Hef lands a job as a promotion copywriter at Esquire, earning $60 a week. When the magazine relocates to New York, Hef’s request for a $5 raise is declined, and he stays behind to found his own magazine. 1952 Hef tries to save money while working as the newsstand promotion director of [...]

A British magazine once estimated that Hugh M. Hefner had made love to 3000 women in his lifetime. An exaggeration, Hef says (but fails to supply corrected statistics). The important thing, he pointed out to Bill Zehme, his Playboy Interviewer in the January 2000 issue, is quality, not quantity. In fact, the first thing Mr. [...]

Be the first to know the latest news and gossip about Hef and Playboy as our founder chronicles his every move on his up-to-the-minute Twitter feed. Bookmark this page to follow his real-time updates about the magazine, Mansion, and all the lovely ladies that grace our pages and pass through Hef’s palatial estate. You can [...]

Bill Zehme sheds some light on Crystal and Hef's relationship—before their wedding was abruptly called off. Read the full interview.

2000 On April 11, the City of Chicago renames a portion of downtown’s Walton Street—the location of the original Playboy Club—Honorary Hugh M. Hefner Way. 2000 On April 13, Hef—flanked by Mandy and Sandy Bentley—rings the closing bell at the New York Stock Exchange. 2000 A tuxedo-clad Bill Maher pays homage to Playboy After Dark [...]

2010 On December 24, Hef proposed to girlfriend Crystal Harris, Miss December 2009. Their engagement was announced by Hef on Twitter on Christmas Eve, and the couple was to be wed on June 18, 2011. 2011 On January 12, the feature documentary Hugh Hefner: Playboy, Activist and Rebel was nominated for an NAACP Image Award [...]

1990 Kimberly and Hef’s first son, Marston Glenn, is born on Hef’s birthday, April 9. 1991 Kimberly and Hef’s second son, Cooper Bradford (named for Agent Cooper on TV’s Twin Peaks), is born on September 4. 1992 David Lynch and Mark Frost, the creators of TV’s Twin Peaks, premiere their documentary Hugh Hefner: Once Upon [...]

1971 Playboy Enterprises buys the Playboy Mansion West in the Holmby Hills district of Los Angeles, which becomes Hef’s new home. Take a 3-D tour of the Playboy Mansion» 1971 Playboy goes public. The first Playboy Enterprises-incorporated stock certificate is illustrated with a reclining nude Playmate. 1971 Hef meets Bunny-in-training and future Miss December Karen [...]