Today Hugh Hefner celebrates his 88th birthday from a unique vantage point: in the midst of the continuing celebration of Playboy’s 60 years in print. That the magazine—once little more than a notion in the mind of a frustrated 25-year-old copywriter—was ever anything less than the titan of sex, style and sophistication it is now seems like a funny dream. But it takes more than the blink of an eye to build something historic, and we’ve taken the liberty of charting out the meteoric trajectory of the Playboy brand and the man behind it all in its 60 years of reshaping the American cultural landscape—for the better, for the smarter and certainly for the sexier. Click around the timeline below to explore the rich history of Playboy and Hugh Hefner in film and photography.

We at offer you our sincerest wishes of happiness on your 88th birthday, Hef. Here’s to many more years of history in the making. Cheers!

December 1953

Hugh Hefner launches Playboy with $10,000 cash, the product of personal loans and 40 early investments. With its sophisticated-yet-playful sexuality, there’s nothing else like Playboy on newsstands. The first issue, featuring a then-unknown Marilyn Monroe, goes to press without a date and sells around 54,000 copies, unprecedented for an unpublicized new periodical. Within two years, Playboy has become one of the best-selling men’s magazines on the market. Bolstered by his success, Hefner successfully defends his right to the mailing privileges used by standard periodicals, defeating the U.S. Postal Service in court. Hefner’s trailblazing ways imbue the now-iconic Rabbit Head logo with a significance that transcends his blockbuster magazine. A legendary brand is born.

1959: Television, Real Estate & the Jazz Fest

Hugh Hefner extends his reach into homes across America with the launch of his first late night talk show, Playboy’s Penthouse. This foray into television will later spawn a film production company and a follow-up series, Playboy After Dark. In the same year, Hef organizes the inaugural Playboy Jazz Festival, featuring such legends as Louis Armstrong and Ella Fitzgerald. With the purchase of his first infamous Playboy Mansion in Chicago, Hefner rides his burgeoning empire into the ’60s.

1960: The Playboy Club

The first Playboy Club opens in Chicago. Featuring world-class and local entertainers alike, the club proves so popular that dozens more crop up across America, inviting the average American man into the Playboy lifestyle. But the glamour isn’t exclusive to the guests; the staff’s distinctive attire and allure gives way to another world-famous cultural icon: the Playboy Bunny.

1962: Hugh Hefner Raises His Voice

Under Hugh Hefner’s editorial direction, the magazine christens the long-form Playboy Interview with a conversation with jazz legend Miles Davis. The franchise, an editorial institution in the making, will go on to feature some of the world’s sharpest minds and brightest stars, from Jimmy Carter to Muhammad Ali. In December, Hefner publishes the first of 25 installments of The Playboy Philosophy, establishing himself and Playboy as the activist arbiters of the sexual revolution to come.

1971: Playboy Goes Public

Hugh Hefner’s Playboy Enterprises, Inc. goes public, legitimizing the company as a name to invest in. Hefner purchases the Playboy Mansion West in L.A., and “The Mansion” quickly grabs the public’s attention as an epicenter for raucous celebrity- and Playmate-filled parties. Featuring countless bedrooms and secret passages, a screening room and the infamous grotto, the large Holmby Hills estate becomes the crown jewel of the brand.

1972: A Bunny Abroad

Playboy Magazine hits peak circulation as the November 1972 issue sells an all-time high of 7.16 million copies, kicking off four consecutive months of sales over seven million. Taking the success in stride, the magazine launches its first international editions in Germany and Italy, eventually spawning 29 foreign editions sold in more than 50 countries.

1979: West Coast Blues

Playboy reaches another milestone as it celebrates 25 years in print. With Playboy Clubs open around the world and a near global editorial presence, Hugh Hefner looks back to 1959 for inspiration, relaunching the Playboy Jazz Festival, this time on the West Coast at the legendary Hollywood Bowl. Ticket sales set a new record for the venue and Hefner announces that the Jazz Festival will become an annual event.

1989: The Great Canadian Beauty

In the summer of 1989, Canadian beauty Pamela Anderson is discovered after she’s shown on the big screen during a B.C. Lions football game in Vancouver. The event propels Anderson onto the October cover of Playboy. Five months later, she’s Miss February 1991. Pamela eventually appears on the cover a total of 13 times—more than any other model or Playmate. With every new credit in film or television, Anderson becomes one of the most successful members of the Playboy family.

1994: Playboy Dials In is born. Playboy is the first national magazine to launch its own website, featuring exclusive pictorials and editorial content for an online audience. Having been officially renamed Playboy TV, the television channel expands into 24-hour programming and is among the first networks launched on DirectTV.

2003: The Golden Jubilee

Playboy turns 50, marking another unprecedented milestone. To honor Playboy’s legacy and future, the company throws 50 parties in 50 cities around America and releases a 50th Anniversary collector’s issue alongside other limited-edition merchandise. Months of celebration are capped off with lavish invite-only parties at the Playboy Mansion and the New York Armory.

2013: Sixty and Sexier than Ever

Six decades in and still going strong, Playboy celebrates its latest milestone with parties in New York and London. The 60th Anniversary issue goes to print with a splash, featuring the world’s most famous supermodel on the cover: Kate Moss. The English superstar’s Mert and Marcus–shot pictorial creates a field day for press around the world as the beautiful photos are immediately shared on blogs, news websites and social media.

April 9, 2014

He’s a creature of habit! Hugh Hefner celebrates his birthday in style with an annual viewing of Casablanca. Gentlemen in white tuxes greet women bedecked in their finest gowns before a glamorous evening of cocktails and film noir, all in the name of the great man behind the iconic Rabbit Head logo, Hugh Marston Hefner. Here’s looking at you, kid.