For Hugh Hefner, Los Angeles was home. The late Playboy founder, who died of natural causes on Wednesday in his famous Holmby Hills mansion, was drawn there in the early 1970s and never left. He threw legendary parties that lured in Hollywood’s A-list; he starred in a reality show that revitalized his public reputation as a long-standing Lothario; and he saved the the iconic Hollywood sign that rests high up in the hills. Twice.

Erected in 1923, the Hollywood sign (which originally spelled out “Hollywoodland”) was long a symbol of glamorous Tinseltown dreams. But by 1978, it had started to deteriorate after years of neglect. By that time, Hugh Hefner was already a famous L.A. resident and a household name. The Chamber of Commerce needed a quarter of a million dollars to revitalize the sign—and got just that after Hefner became involved in restoration efforts. As The Hollywood Reporter writes, he threw a lavish fund-raiser, auctioning off letters from the old sign for $27,000 each. Buyers included rock stars like Alice Cooper and actors like Gene Autry, who ended up giving enough to restore the Mount Lee plot with new letters. The Hollywood Hills were empty for about three months after that until the chamber was able to replace it with a new sign.

A few decades later, Hefner would come to the rescue once again. Back in 2010, a conservationist group—the Trust for Public Land—was rallying to protect the 138 acres around the sign from developers, who wanted to build luxury properties on Mount Lee. The trust was given an ultimatum of sorts: pay $12.5 million now, and the acres are yours. As the deadline approached, it was able to raise nearly all the cash, but ended up short about $1 million. And it only had about a week and a half left to raise the rest.

Cue Hefner, who was alerted in the nick of time and donated the final $900,000. “It would have been a real shame after having restored it if it wound up sold,” he told People a few days later. “It’s become something iconic and represents not only the town but represents Hollywood dreams, and I think that’s something worth preserving.”