Matt Dillon has had a fascinating career on the silver screen. After becoming a favorite actor for the legendary filmmaker Francis Ford Coppola to cast in his youth-centric films in the 1980s, Dillion subsequently became one of the industry’s greatest heartthrobs.
While he often worked in mainstream material, Dillion was usually willing to take a chance on rising independent projects from auteur filmmakers like Cameron Crowe and Gus Van Sant. Between wacky comedy, disturbing true crime, and unnerving satire, Dillon can tackle nearly any genre.
10 ‘Crash’ (2005)
2005’s Crash is not a film that is remembered fondly by award-season fanatics. The film’s victory at the Academy Awards, which took home the Oscars for Best Picture and Best Original Screenplay, felt egregious in a year and included future classics like Brokeback Mountain, Capote, Munich, Good Night, and Good Luck.
Crash’s simplistic depiction of racism and systemic dysfunction may not have aged well, but that isn’t the fault of its stars. In fact, Dillon’s terrifying performance as a racist police officer that has a change of heart is one of the film’s few bright spots.
9 ‘The Outsiders’ (1983)
Although Coppola’s work in the 1980s was never going to match his legendary run of hits in the 1970s, it was fascinating to see the legendary director turn his focus into telling true stories about the realities of the American experience.
The Outsiders was a particularly grim depiction of the mythology behind masculine social groups in the 1950s, and served as a terrific breakout film for such stars as C. Thomas Howell, Ralph Macchio, Patrick Swayze, Rob Lowe, Emilio Estevez, and a young Tom Cruise. However, it was Dillon who stole the film with his hard-edged performance as the “Outsiders’” senior member, known as “Dally.”
8 ‘My Bodyguard’ (1980)
They don’t make movies like My Bodyguard anymore; this sweet, sensitive, coming-of-age dramedy has a lot of empathy for all its characters and shows a more complex understanding of bullying than most of its counterparts in the same era.
The film follows the young boy Clifford Peache (Chris Makepeace) as he attempts to survive his new school and the constant bullying of the ruthless bully Melvin Moody (Dillon); to protect himself, Clifford hires the school’s toughest older boy Ricky Linderman (Adam Baldwin) to be his personal bodyguard. It’s an amusing yet surprisingly honest satire of toxic masculinity.
7 ‘Wild Things’ (1998)
Wild Things is a brilliant satire of the “whodunit” neo-noir genre that had become increasingly popular within the 1990s; the film is so sleazy and features characters that are so eccentric that it’s hard to not laugh at how ridiculous each subsequent twist gets.
Dillon gives a sardonic, despicable performance as a respected high school guidance counselor who is accused of harassing two of his top students. It was an inherently unlikeable character that Dillon excelled with, as the film’s increasingly ridiculous misdirections allowed him to play into the character’s eccentricities.
6 ‘To Die For’ (1995)
Dillon’s collaborations with Gus Van Sant marked one of the most fruitful periods in both of their careers. To Die For was a brilliant deconstruction of media sensationalism and the cult of personality that utilized Dillon’s “bad boy energy” for satirical purposes.
Nicole Kidman gives one of the best performances of her career as the aspiring celebrity reporter Suzanne Stone-Maretto, with Dillon appearing as her hapless husband, Larry. Larry is at first impressed by his wife’s rise to prominence but finds he can no longer keep up with a woman whose emotions feel increasingly plastic.
5 ‘There’s Something About Mary’ (1998)
Peter and Bobby Farrelly were highly influential comedy filmmakers in the 1990s who developed the “gross-out” genre cleverly. There’s Something About Mary is one of their funniest films to date.
While Cameron Diaz’s breakout performance as the titular girl made the film so beloved, the impressive ensemble included terrific performances from co-stars such as Ben Stiller, Keith David, Lee Evans, Chris Elliot, and Jeffrey Tambor. Dillon stands out with his ridiculously evil depiction of the manipulative private detective Pat Healy, who is willing to do anything to get in Mary’s good graces.
4 ‘The House That Jack Built’ (2018)
Dillon had been absent from the public spotlight for a vast majority of the 21st century, but he had a major comeback role in what was easily the darkest film of his career. Lars von Trier’s controversial style of filmmaking is known for generating strong reactions, but the acclaimed Danish filmmaker has never made a film as artfully disgusting as The House That Jack Built.
Dillon played the titular role in this highly disturbing serial killer film; the nervous energy he brought to the role made the character of Jack feel even more disturbing.
3 ‘Singles’ (1992)
Cameron Crowe has a unique ability to encapsulate an entire generation’s culture, and Singles chronicles the rise of the grunge movement in a nearly perfect way. The film focuses on a group of “Gen X” young adults who attempt to make a living in New York City during the height of the grunge phenomenon.
Dillon has a particularly amusing role as Cliff Poncier, a goofy musician who thinks that betting on his own success is the only thing he’ll ever need to launch a career in the industry.
2 ‘Drugstore Cowboy’ (1989)
Dillon’s best project with Van Sant still feels like an outlier in independent cinema. Drugstore Cowboy is a frank, unflinchingly honest examination of drug abuse within young adults, and wasn’t afraid to show the serious repercussions that addiction can have.
Dillon stars as the wild thief Bob Hughes, who travels across the country with his wife Diane (Kelly Lynch) and his gang as they steal prescription medications from various pharmacies to support their addiction. Watching Bob sink deeper into his self-destructive habits makes for a disturbing yet eye-opening viewing experience.
1 ‘Rumble Fish (1983)
Although it was released the same year as another one of Coppola’s dark coming-of-age dramas, Rumble Fish is perhaps his most underrated film as a director. It’s certainly the film that put Dillon on the map; he stars as the teenage troublemaker Rusty James (Dillon), who struggles to conform to society as he seeks the guidance of his enigmatic older brother (Mickey Rourke).
Dillon captures Rusty’s internal struggle to live up to preconceived notions of masculinity; as he watches society change around him, he’s left feeling like he no longer has a place.
KEEP READING: ‘The House That Jack Built’ Is Extremely Violent, But Lars von Trier Has a Reason For It