Heads up, friends: We will be laugh-crying today.

Because the world lost a hilarious personality this week. Canadian comic and actor Norm Macdonald died at the age of 61 in Los Angeles on September 14, following a private, nearly decade-long struggle with cancer.

Macdonald’s influence began behind the mic as a stand-up comedian, performing at the Ottawa Yuk Yuk’s amateur night, and eventually at Just for Laughs in Montreal. He put his straight-faced wit to work writing for the Roseanne sitcom in the early ’90s before being recruited by 30 Rockefeller Plaza.

Then, from ’93 to ’98, he performed on Saturday Night Live, quickly earning a spot in the Weekend Update anchor’s chair. Chevy Chase, the bit’s creator, later called him “the only other guy who did [the segment] funny.”

Through the rest of his career in film, TV, sports commentating, voice acting, comedy, and more, Macdonald used his unique insight and deadpan delivery to make people laugh, think and sometimes squirm.

“Comedy is surprises,” he famously said, “so if you’re intending to make somebody laugh and they don’t laugh, that’s funny.”

Here are some of Norm Macdonald’s funniest moments. RIP, legend.