The comedy world has lost one of its legends. Charles Grodin, a dependably hilarious presence in films, television shows, and on Broadway for more than 50 years, has died. He was 86 years old. His son told The New York Times that the cause of death was bone marrow cancer.

Although Grodin was best known as a comic leading man, he had a long career as a writer as well. He won an Emmy writing a TV special for Paul Simon, and penned numerous plays and books throughout his life. In the 1990s, he also shifted away from acting for a time and became a TV commentator and pundit. From 1995 to 1998, he hosted The Charles Grodin Show on CNBC.

Still, most will remember Grodin for his memorable performances in film comedies. Although he had small roles in 20,000 Leagues Under the Sea and Rosemary’s Baby, and found some success on Broadway, his real breakthrough came in 1972’s The Heartbreak Kid, directed by Elaine May and written by Neil Simon. He starred as a nebbish who marries a nice Jewish girl then immediately falls for a blonde bombshell on his honeymoon.

Grodin followed The Heartbreak Kid with several more memorable films, including the 1976 King KongHeaven Can Wait, Albert Brooks’ Real Life, and The Incredible Shrinking Woman. May cast Grodin again her infamous flop (that’s actually very funnyIshtar, where he played a scheming CIA agent. Most of these roles made smart use of Grodin’s great gift for understatement; he played everything so small and so dry, that even a slight rise in his voice or a raise of his eyebrow could elicit a laugh.

A few years later came what may be Grodin’s funniest performance: As cunning mob accountant Jonathan “The Duke” Mardukas in 1988 Midnight Run. Grodin and co-star Robert De Niro made one of the very best onscreen buddy duos in history. In this classic scene, Grodin pretends to be an FBI agent to con some money out of a small-town bartender.

’90s kids may also remember Grodin from his role as the exasperated father in the Beethoven movies.

Grodin was never even nominated for an Academy Award, despite several worthy performances. That’s unfortunate, but a body of work as good as Grodin’s will be remembered no matter how many awards he did or didn’t win.

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