Kings of Comedy: Funny Performances That Won at Oscar

While more serious fare tends to dominate at the Oscars, sometimes a comedic performance gets to go home with the gold. We take a look at 11 noteworthy comedic supporting turns that either scored a nod or won the award. By Phil Pirello

It’s hard to pull off a character so “love to hate” as Hill's Donnie Azoff, a corrupt, ‘lude-tripping, cousin-marrying stockbroker in Wolf of Wall Street. But Hill effortlessly pulls it off, finding the right balance between funny and serious – bringing his improv A-game as DiCaprio’s right-hand scumbag.

Kline deservedly earned his BSA Oscar thanks his scene-stealing role in Wanda. In this farcical caper, Kline portrays a borderline-manic thief in way over his head. In lesser hands, the role could have been reduced to over-the-top scene-chewing. But Kline gives each scene exactly the right amount of whatever it needed.

Arkin has the market cornered when it comes to playing sage-like characters with dry wits and big hearts. And arguably it all started with his BSA Oscar-winning role as Sunshine’s “tell-it-like-it-is” grandpa. This is career-best work, and less-is-more acting at its most resonate.

As the straight-man butler to Dudley Moore’s titular buffoon, Gielgud gives the film its much-needed heart in between delivering most of Arthur’s best one-liners.

The 1944 musical Going My Way scored Fitzgerald both a Best Actor and Best Supporting Actor at that year’s Academy Awards. He lost out on the former, but more than earned himself the latter for his portrayal of an old-guard priest who gets into comedic conflict with his younger replacement.

Everyone remembers Gooding’s amped-up “Show Me the Money” set piece, but the BSA Oscar-winner is even better during the film’s quieter, more heartfelt moments as a down-and-out football star with an ego bigger than the stadiums he plays in. While the movie is named after Tom Cruise’s character, its “qwon” belongs to Rod Tidwell.

Really? You haven’t seen this comedy classic?! Why do you hate fun? What did laughter ever do to you?  Burns is crazy good in this two-hander from writer Neil Simon, about a vaudeville duo reuniting for a TV special despite the fact that they hate each other. Burns won Best Supporting Actor.

Palance subverted audience expectations in this hit 1991 comedy for which he won Best Supporting Actor. As the gruff Curly, Palance gives a very funny and sentimental portrayal as a veteran cowboy stuck babysitting “city folk.” (We'll ignore the sequel, The Legend of Curly’s Gold.)

Put this classic on a double bill with Sunshine Boys and thank us later. Coburn stars as one-third of a matchmaking farce set in a D.C. apartment building, playing Cupid opposite Jean Arthur and Joel McCrea. While the comedy is tame by today’s standards, Merrier still manages to get its share of big smiles and belly laughs.

Lemmon has many great comedic turns on his resume jockeying for the “Funniest Role Ever” spot on his CV. One could make a good argument for his work in Mister Roberts to take the top spot. It makes great use of the chemistry between the boat’s Captain, Henry Fonda, and Lemmon's excitable ensign. As comedy classics go, you’d be hard-pressed to find better.

Matthau’s work in this 1966 comedy is pure gold, as in Best Supporting Actor gold. Matthau plays a crooked lawyer in search using his brother-in-law’s fake injury to win a big cash settlement. Almost 50 years since he won the award, Matthau’s deadpan humor and impeccable comic timing rivals that of today’s best comedic performers.