On Saturday, legendary observational standup and Tonight Show favorite David Brenner passed away peacefully in New York City after a battle with cancer. “David Brenner was a huge star when I met him and he took me under his wing,” fellow standup Richard Lewis said in a statement. “To me, historically, he was the godfather of hip, observational comedy. He mentored me from day one. … His passing leaves a hole in my life that can never be replaced.” Throughout the ‘70s and ‘80s, Brenner became a frequent guest on Johnny Carson’s The Tonight Show, with over 150 appearances as both guest and substitute host. He also starred in four HBO specials and briefly hosted his own but short-lived talk show Nightlife in 1986.
According to his obituary in The New York Times, Brenner’s sense of humor lasted until his final moments. “In David’s final request,” his family said in a statement, “he asked that $100 in small bills be placed in his left sock ‘just in case tipping is recommended where I’m going.’” Brenner was 78 years old.
Click through to watch some of Brenner’s most memorable Tonight Show moments.