Shelley Berman, the wildly popular “sit-down” comic of the late 1950s and ’60s who, after his career came unhinged following an outburst caught on camera, concentrated on acting and played Larry David’s father on Curb Your Enthusiasm, has died. He was 92.

A standout in a golden era of comedy that included other observational masters like Mort Sahl, Lenny Bruce and Bob Newhart, Berman died early Friday morning at his home in Bell Canyon, Calf., according to a post on his official Facebook page. He had a long battle with Alzheimer’s disease.

Inside Shelley Berman, his live record released in 1959, became the first comedy album to go gold (reaching sales of 500,000 units) and was the first non-musical recording to win a Grammy Award.