Tough week: the Los Angeles Police Department has confirmed that comedian Garry Shandling died Thursday in a Los Angeles hospital after suffering a massive heart attack. He was just 66.

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Shandling began his career in 1975 as a writer for the sitcoms Sanford & Son and Welcome Back, Kotter—two classics of the era—but he truly shone as a comedian, and from ‘86 to ‘90 had created a successful namesake series for Showtime called It’s Garry Shandling’s Show. It had a wacky theme song.

In 1992, Shandling debuted the awesome Larry Sanders Show, which mined Shandling’s experiences guest-hosting The Tonight Show in a fictional narrative that cast “Larry Sanders” as the beleaguered host of a late-night talk show. Its dry humor and the sardonic exploration of mundane situations set the tone for the comedy of the era, and reflected back the tenor of the Clinton years; it was also where many comedians got their big breaks. Janeane Garofalo and Sarah Silverman both played sarcastic staffers, a talent booker and staff writer, respectively; the latter had a character arc that mined her real-life experiences with sexism as a writer on Saturday Night Live, and gender in the workplace was explored quite frequently:

Once Larry Sanders ended in ‘98, he went on to star in several films and television shows, and he served as host of awards shows (the Grammys, the Emmys) as well as performing stand-up. But the Larry legacy remained deeply influential, and in 2012 the cast reunited for a special issue of Entertainment Weekly. From that interview:

Would you ever consider getting the Larry Sanders cast back together for another go-round on TV or in a movie?

My only thought is, maybe when Larry dies we’ll do something on Access Hollywood. We’ll get a bunch of stars to just go on and on about Larry and what it was like to be on his talk show. [Laughs] I think we could probably fool a number of people.

He was funny until the very end.