The man who founded Playboy in 1953 has passed away at age 91. Even aside from creating a media empire, Hef lived a pretty interesting life.

He Was Fascinated With Marilyn Monroe

Part of the reason why Playboy the magazine took off right away is because of its marketing hook: issue no. 1 featured racy images of Marilyn Monroe, the biggest sex symbol and movie star of the day. Monroe didn’t exactly pose for the brand-new publication. Hefner acquired the pictures from photographer Tom Kelly, who took the photos in 1949, long before Monroe was world-famous. Kelly paid Monroe $50; Hefner paid Kelly $500. That first issue of Playboy with Monroe on the cover sold a whopping 50,000 copies. Hefner’s public life began with Monroe, and he’ll be near her always. In 1992, he bought the funeral plot at Los Angeles’s Westwood Village Memorial Park immediately adjacent to Monroe’s. It cost him a mere $75,000.

He Was a Talk Show Host

From 1959 to 1960, Hefner hosted a Playboy-branded talk show called Playboy’s Penthouse. Syndicated to TV stations around the country, it was taped at a studio in Chicago was dressed to look like Hefner’s stylish, swingin’ bachelor pad. Playboy models and “Playmates” served as extras while Hefner casually interviewed celebrities and musicians. A decade later, the show was revived, only shot in Los Angeles and with the title Playboy After Dark.

He’s Synonymous With Rabbits

The logo of all Playboy products is a sophisticated bunny—the Playboy Bunny—and cocktail waitresses at Hefner’s chain of Playboy Clubs in the ‘60s and ‘70s wore skimpy bunny costumes. Hefner also donated money to conservation causes to protect an endangered species of marsh rabbit. In recognition of Hefner’s love of all things leporine, in 2010 the rabbit was named Sylvilagus palustris hefneri.

He Owned the Letter Y

Hefner, an icon of Los Angeles and the Hollywood lifestyle (in part because of Playboy, and in part because of the Playboy Mansion), gave back to La La Land in 1978. He organized a drive to restore the famous Hollywood sign. He hosted fundraisers at his mansion and won the auction to “buy” the letter “Y” in Hollywood. Or rather, he paid for its restoration costs of $27,000.