The actor, author, and talk show host Charles Grodin died at his home in Connecticut on Tuesday at the age of 86 years old. With a hempishly dry and indefatigably probing sense of humour, Grodin forged a career on the shabby margins of the mainstream, and remains best known for the classic comedy capers The Heartbreak Kid and Midnight Run.

Born to Orthodox Jewish parents in Pittsburgh, Grodin graduated as valedictorian from Peabody High School then dropped out of the University of Miami to pursue acting. He scored success on Broadway beginning with the 1962 opening of the romantic comedy Tchin-Tchin, where he took a supporting role opposite the stars Margaret Leighton and Anthony Quinn.

After a small but memorable part as the complaisant obstetrician Dr. Hill in the 1968 psychological horror Rosemary’s Baby, Grodin received his big break on the silver screen courtesy of the 1972 comedy The Heartbreak Kid. Directed by Elaine May from a screenplay by Neil Simon, the film saw Grodin cultivate a heedless and striving persona as the callow sporting goods salesman Lenny Cantrow, who quickly forgoes his Jewish wife for a sun-kissed blonde from the Midwest.

Giving his sunburnt bride the runaround in Miami or extolling the honesty of Minnesotan fare with a droll humour which sometimes borders on the absurd, Grodin was already adept at turning the comic spotlight on his colleagues. At the 45th Academy Awards, The Heartbreak Kid was celebrated with supporting nominations for his costars Eddie Albert and Jeannie Berlin.

Elaine May and her erstwhile comic partner Mike Nichols evidently saw something in Charles Grodin, who was reportedly offered the lead role in The Graduate before accepting a small part in Nichols’ next feature Catch-22. In 1978, Grodin starred in the comic fantasy Heaven Can Wait with its screenplay by Elaine May and Warren Beatty, and in 1987 he played opposite Beatty and Dustin Hoffman in May’s maligned adventure-comedy Ishtar.

In the meantime Grodin returned to the stage, in 1974 directing the Broadway play Thieves by Herb Gardner, then starring opposite a Tony Award-winning Ellen Burstyn in the romantic comedy Same Time, Next Year by Bernard Slade. Grodin hosted Saturday Night Live and received an Emmy Award as one of the writers for a Paul Simon television special, and he became a frequent guest on the late-night talk circuit where his combative exchanges with Johnny Carson and David Letterman alternately wrought confusion and delight. In 1979, Grodin played the family patriarch in the spoof documentary Real Life by Albert Brooks.

In 1985 Grodin assembled an all-star cast as the writer and producer of the Hollywood satire Movers & Shakers, which despite the assorted talents of Walter Matthau, Steve Martin, and Gilda Radner received limited distribution and ultimately flopped. His second wind as an actor came opposite Robert De Niro in the cult 1987 comedy Midnight Run. Grodin plays Jonathan ‘The Duke’ Mardukas, an inveterate fraudster who strikes up a slow-burning friendship with the bounty hunter Jack Walsh. Written by George Gallo and directed and produced by Martin Brest, with support from Yaphet Kotto, John Ashton, Dennis Farina, and Joe Pantoliano, Midnight Run endures as one of the essential buddy films.

A brief dalliance with the mainstream courtesy of the first two Beethoven movies ended with a long hiatus from film. Grodin hosted his own talk show on CNBC and worked briefly as a political correspondent for 60 Minutes II. At home with his family he devoted more of his time to his second career as the successful author of humorous observations and behind-the-scenes anecdotes, before slowly finding his way back to the screen.

Between film cameos and episodes of Law & Order and The Michael J. Fox Show, a late career highlight came over a couple of seasons as Dr. Bigelow in the FX comedy Louie between 2014 and 2015. Whether treating Louie’s ailments with philosophical scorn or conciliating with his patient’s daughter Jane, played by the wonderful Ursula Parker, Grodin brought a sense of assurance and opportunity to every scene.

Charles Grodin was a passionate supporter of The Innocence Project and received a William Kunstler Award for Racial Justice for his advocacy on behalf of non-violent inmates. According to his son Nicholas, bone marrow cancer was the cause of his death.