In 1978,
Jane Bernstein and a friend were helping director
Jonathan Kaplan cast the teen drama
Over the Edge when they found Dillon cutting class at
Hommocks Middle School in
Larchmont. Dillon auditioned for a role and made his debut in the film. The film received a regional, limited theatrical release in May 1979, and grossed only slightly over $200,000. Dillon's performance was well-received, which led to his casting in two films released the following year: the teenage sex comedy
Little Darlings, in which
Kristy McNichol's character loses her virginity to a boy from the camp across the lake, played by Dillon, and the more serious teen
dramedy My Bodyguard, where he played a high-school bully opposite
Chris Makepeace. The films, released in March and July 1980, respectively, were box office successes and raised Dillon's profile among teen audiences. Another of Dillon's early roles was in the
Jean Shepherd PBS special
The Great American Fourth of July and Other Disasters. The only available copies of this film are stored at UCLA, where a legal dispute makes it unavailable to the public. One of his next roles was in ''
Liar's Moon'', where he played Jack Duncan, a poor Texas boy madly in love with a rich banker's daughter. He won the role of Dallas "Dally" Winston in
Francis Ford Coppola's 1983 cinematic adaptation of
S. E. Hinton's
novel,
The Outsiders, and shared the screen with an ensemble cast that included
Tom Cruise,
Emilio Estevez,
Leif Garrett,
C. Thomas Howell,
Diane Lane,
Rob Lowe,
Ralph Macchio, and
Patrick Swayze. He had previously appeared in another adaption of one of Hinton's novels with Emilio Estevez,
Tex (1982), and he and Diane Lane appeared in Coppola's second adaptation of a Hinton novel,
Rumble Fish (1983). All three films were shot in
Tulsa, Oklahoma, Hinton's hometown. He followed those up with
The Flamingo Kid in 1984. He made his
Broadway debut with the play
The Boys of Winter in 1985. Dillon did voiceover work in the 1987 documentary film
Dear America: Letters Home from Vietnam. In 1985, Dillon was namechecked in the lyrics of the
Roger Daltrey song 'After The Fire' (written by
Pete Townshend). In 1989, Dillon won critical acclaim for his performance as a drug addict in
Gus Van Sant's
Drugstore Cowboy. Dillon continued to work in the early 1990s with roles in films like
Singles (1992). He had a resurgence when he played
Nicole Kidman's husband in
To Die For (1995), as well as starring roles in
Wild Things (1998) and ''
There's Something About Mary'' (1998), for which he received an
MTV Movie Award for Best Villain. In 2002, he wrote and directed the film
City of Ghosts, starring himself,
James Caan and
Gérard Depardieu. In 2005, he starred in
Factotum, a film adaptation of an autobiographical work by
Charles Bukowski. The same year he received critical praise and earned
Best Supporting Actor Golden Globe and
Academy Award nominations for his role in
Crash, a film co-written and directed by
Paul Haggis. In 2005, Dillon co-starred in
Disney's Herbie: Fully Loaded and on March 11, 2006, hosted
Saturday Night Live, in which he impersonated
Greg Anderson and
Rod Serling in
sketches. Dillon starred in the comedy
You, Me and Dupree, opposite
Kate Hudson and
Owen Wilson. The film opened on July 14, 2006. On September 29, 2006, Dillon was honored with the
Premio Donostia prize in the
San Sebastián International Film Festival. Dillon contributed his voice as the narrator,
Sal Paradise, in an audiobook version of
Jack Kerouac's novel
On the Road. In 2006, he narrated
Once in a Lifetime: The Extraordinary Story of the New York Cosmos. Dillon appeared in several music videos during his career. He made a cameo appearance as a detective in
Madonna's
Bad Girl music video which also stars
Christopher Walken. Dillon appeared in 1987 in the music video for "
Fairytale of New York" by the Irish
folk-punk band
The Pogues, playing a cop who escorts lead singer
Shane MacGowan into the "drunk tank". In 2007, the band
Dinosaur Jr. hired Dillon to direct the video for their single "Been There All The Time" from the album
Beyond. That year, he guest-starred on
The Simpsons episode "
Midnight Towboy". Early in 2015, he played the role of a
Secret Service agent in the
FOX 10-episode series
Wayward Pines. In 2018, Dillon played the lead role in the
Lars von Trier thriller
The House That Jack Built. He portrayed
Marlon Brando in the biopic about
Maria Schneider Being Maria, which premiered at the
2024 Cannes Film Festival. ==Personal life==