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Garry Shandling, the Emmy-winning stand-up comedian who created and starred in one of TV’s most influential comedies with The Larry Sanders Show, died in Los Angeles on Thursday. He was 66.

Shandling suffered a heart attack, his publicist told EW. He was transported to a local hospital where he died, a Los Angeles Police Department spokesperson said.

Born in Chicago and raised in Tucson, Arizona, Shandling graduated from the University of Arizona before moving to Los Angeles and pursuing a TV writing career. He began by writing for Sanford & Son and Welcome Back Kotter, and then turned to stand-up, where he would win over audiences with his pained, neurotic, dry, and otherwise sharp riffs. He and Alan Zweibel created Showtime’s Emmy-nominated and fourth wall-breaking It’s Garry Shandling’s Show (1986-1990), in which Shandling played a sitcom character version of himself who was aware that he was just in fact a character, and one who talked to the audience.

A frequent guest and guest host of The Tonight Show with Johnny Carson, Shandling was considered to take over as host of the show when Carson retired, and he would be a candidate for other late-night gigs. Instead, he would shrewdly send up the genre with HBO’s The Larry Sanders Show (1992-1998), a fictional look at the behind-the-scenes shenanigans of a late-night talk show. Created by Shandling and Dennis Klein, the single-camera comedy — which starred Shandling as the vain, insecure, and self-obsessed late-night host Larry Sanders — was a hilarious insider peek at the pettiness and absurdity of Hollywood, but instead of going cartoonish, it was rooted in authenticity — and awkwardness.

“I thought I could make the talk show look very real so the audience would buy that part and then slowly suck them into the realities of life once Larry goes behind the curtain,” Shandling told EW in 2012. “We were digging into the human condition and reflecting that. Sure, it’s probably more entertaining when it’s a talk show host, but we actually could have done the show in any setting where human beings exist.”

The highly respected and decorated show, which claimed three Emmys, counted Judd Apatow among its writer-producers and featured an all-star cast (including Jeffrey Tambor, Rip Torn, Jeremy Piven, and Janeane Garofolo). Its legacy can be seen everywhere from 30 Rock to Parks and Recreation.

“I’ve always felt that the truth is in the silence,” Shandling said. “I wrote a tweet recently that said, ‘Buddha once said: ha ha ha.’ That is my point. Everything was played with a heavy hand [comedically] at the time on the networks and this show was going to be not that.”

His feature credits include What Planet Are You From? (which he wrote), Zoolander, and Iron Man 2. He most recently played Senator Stern in Captain America: The Winter Soldier. He also appeared with Jerry Seinfeld in a January installment of Comedians in Cars Getting Coffee. In the episode, Shandling reflected on a comedian’s life work. “That material… is purely a vehicle for you to express your spirit and your soul and your being,” he told Seinfeld. “It’s why you’re on the planet.”Data curated by PrettyFamous

The latest issue of EW, which went to press before Shandling’s death, is on newsstands Friday.