Legendary publisher and purveyor of high-class smut Hugh Hefner died Wednesday at the age of 91.

The founder of Playboy magazine, Hefner became known for many things during his long lifetime: his longtime residency in the Playboy Mansion, his many marriages, and a strange affinity for smoking jackets, to name a few. But here at Curbed, we’ll always remember Hefner as a guardian of LA’s most recognizable landmark: the Hollywood Sign.

Long before the sign became the closely guarded, increasingly difficult to access, tourist attraction that it is today, it was a slowly deteriorating advertisement for a real estate development that no one had ever bothered to take down.

By 1978, the sign, which originally read “Hollywoodland,” had been in place on the side of Mount Lee for 55 years and was in a state of severe disrepair. The Hollywood Chamber of Commerce decided that the only way to preserve the sign was to completely replace its enormous letters at a cost of $250,000—not a small sum at the time.

To raise the money, Hefner held a fundraising event at the Playboy Mansion (the invitation simply read, “To Save The Hollywood Sign, RSVP Marsha 469-8311”) in which individual letters were auctioned off to the many notable guests in attendance. Rocker Alice Cooper purchased an “O,” while singing cowboy Gene Autry snagged the second “L.”

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But that wasn’t the only time Hefner came through for the sign. In 2008, a group of Chicago investors listed 138 acres of land beside the “H.” The prospect of a sale provoked fears that a new development could be constructed next to the sign, screwing up sight lines for residents and visitors alike.

In order to avoid that outcome, the Trust for Public Land came up with a plan to buy the property and gift it to the city. Short several million, the trust began soliciting donations to help with the $12 million purchase. Hefner pitched in the last $900,000 to make it happen.

Hikers visiting the sign can reflect on the publisher’s efforts to preserve the singular landmark while sitting on a boulder with his name on it. The Trust for Public Land honored his timely contribution by installing a plaque on a large sitting rock near the sign. It reads, “Hugh Hefner Overlook.”