Shawn’s film career began in the late 1950s,
where he primarily appeared in supporting roles. His first significant breakthrough came with the 1963 classic comedy It’s a Mad, Mad, Mad, Mad World. Shawn played Sylvester, a wild and reckless character who added to the film’s madcap humor. His exaggerated mannerisms and high-energy performance made him a standout in an ensemble cast filled with comedy legends.

It’s a Mad, Mad, Mad, Mad World (1963)

Shawn’s turn as Sylvester Marcus was a comedic triumph. Despite being surrounded by an ensemble of comedy legends like Milton Berle and Sid Caesar, Shawn carved out his own space in the film, delivering memorable moments of chaotic hilarity. His exaggerated movements and nonsensical outbursts added layers of madness to the already frenetic storyline. Shawn played Sylvester Marcus, the hilariously unhinged son of Mrs. Marcus (Ethel Merman). His energetic portrayal of a reckless, motorcycle-riding man-child became one of the film’s highlights. Whether speeding through desert highways or wreaking havoc with his over-the-top antics, Sylvester epitomized Shawn’s signature ability to combine physical comedy with wild absurdity.

The Producers (1967)

Shawn delivered one of his most iconic performances as Lorenzo St. DuBois (L.S.D.), a flower child who is hilariously miscast as Adolf Hitler in the fictional play Springtime for Hitler. His portrayal was a satirical masterpiece, blending cluelessness and charm with biting humor, earning him a permanent place in cult comedy history. Director Mel Brooks often praised Shawn’s improvisational skills and ability to think outside the box, qualities that made his portrayal of L.S.D. so memorable. In interviews, Brooks described Shawn as a comedic genius who brought a singular energy to his roles. He appreciated Shawn’s fearless approach to comedy and his willingness to take risks in his performances. Shawn was supposedly the first person to execute the icon “The High Five”, in the movie. It was during the play in the movie, “Springtime For Hitler”, the character of Hitler played by Shawn sent for Goebbels who was played by David Patch, and instead of putting his hand in front of for the “give me five”, Shawn held it up and Patch slapped it. Though it would not become popular till many years later.

what did you do in the war, daddy? (1966)

In this Blake Edwards-directed film, Shawn played a bumbling American officer caught up in the antics of World War II. Dick Shawn played the character Captain Lionel Cash in the film.

Blake Edwards’s direction brings a mix of slapstick humor and sharp wit, while Dick Shawn’s portrayal of Captain Cash adds to the film’s comedic charm, as his character struggles to maintain order in increasingly chaotic and absurd circumstances.

love at first bite (1979)

Dick Shawn’s performance in Love at First Bite  is a memorable comedic gem in the film. Shawn portrays the flamboyant and eccentric Jeffery Rosenberg, a descendant of Dr. Van Helsing. His character is on a mission to thwart Count Vladimir Dracula (played by George Hamilton), who has arrived in New York City and fallen for a beautiful fashion model, Cindy Sondheim (played by Susan Saint James).

the year without a santa claus (1974)

Shawn lent his voice to the character of Snow Miser in this beloved Rankin/Bass holiday television special, cementing his place in popular culture as the quirky, flamboyant king of frost.

Below is a partial list of Film Appearances:

Way Way Out Movie Premiere
Way Way Out Movie Premiere
LSD The Producers
LSD The Producers
Dick-Shawn-Natalie-Wood-in-Penelope
Dick Shawn and Natalie Wood in Penelope
Mad Mad Word Cast
I’m Coming Mama
Mad Mad World Dancing
Mad Mad World Poster
Made to Order
The Producers #3
The Producers #3
The Producers #4
The Producers
Dick Shawn: Penelope with Natalie Wood
What Did You Do in the War Daddy with James Coburn
Mad, Mad, Mad World
Wake Me When It’s Over with Ernie Kovacs
Way Way Out with Jerry Lewis
What Did You Do In The War, Daddy