During the 1980s and ’90s, Matt Dillon emerged as one of the most prominent stars, amassing a series of blockbuster hits. Initially gaining fame as a teen heartthrob in movies like The Flamingo Kid, Dillon’s breakthrough came with his role in The Outsiders.
He later reinvented himself as a comedic actor in There’s Something About Mary, where he starred opposite Cameron Diaz, whom he dated. At 60, Dillon has found renewed success, particularly after his guest appearance on the sitcom Modern Family, which introduced him to a new generation of fans.
Born on February 18, 1964, in New York, Dillon was raised by his stay-at-home mother, Mary Ellen, and his father, Paul Dillon, a former college golf coach among other roles. Growing up in Mamaroneck with his five siblings, including actor Kevin Dillon, Matt’s early years were steeped in a family environment close to New York City.
Matt Dillon, iconic from the ’80s and ’90s, reflects on his career from teen heartthrob to seasoned actor
Matt’s acting career began unexpectedly when he was discovered while skipping school and cast in Over the Edge at just 14. Reflecting on this in a 2023 Parade interview, Dillon acknowledged the role’s impact on his career. He noted, “Had that casting agent offered me a role in a more generic film, my career might have turned out differently.”
Following this, Dillon featured in popular teen movies such as Little Darlings and My Bodyguard, both of which were well-received at the box office. However, it was his portrayal of Dallas in the 1983 film The Outsiders, directed by Francis Ford Coppola, that solidified his stardom and remains one of his most iconic roles to this day.
Dillon shared with Parade last year that the film continues to attract new fans, saying, “Even now, kids at my old junior high school still ask about the characters. It has truly become a classic.” He subsequently appeared in another Coppola film, Rumble Fish, which was also based on an S.E. Hinton novel, with whom Dillon maintains a longstanding friendship.
Critical acclaim followed with roles such as a drug addict in the 1989 film Drugstore Cowboy and as Nicole Kidman’s unfortunate husband Larry in To Die For. Dillon also starred in the 1998 hit Wild Things.
His role as private investigator Pat Healy in There’s Something About Mary earned him the MTV Movie Award for Best Villain, and he dated his co-star Cameron Diaz during this period.
Diaz and Dillon began their relationship in January 1996 but kept it low-key. Diaz praised Dillon in interviews, describing him as “one of a kind” and a “great” person. Their relationship ended in 1998 after two years, with Dillon explaining that it simply “ran its course” due to their differing locations and life paths.
Reflecting on their time together in a 2006 Parade interview, Dillon described it as a formative experience, saying, “Cameron was a muse for me, and it was my first deep emotional relationship.” Dillon remains close with co-star Ben Stiller from There’s Something About Mary, sharing fond memories of their time working together.
In 2002, Dillon made his directing debut with City of Ghosts, which he also wrote. The 2000s saw him in various roles, including You, Me and Dupree and Crash, the latter earning him Independent Spirit, Golden Globe, and Academy Award nominations for Best Supporting Actor.
He appeared in the 2018 thriller The House That Jack Built and the 2023 film Asteroid City. Recently, he portrayed Marlon Brando in the biopic Being Maria, which premiered at the Cannes Film Festival.
Despite his film career, Dillon has embraced television, appearing in Modern Family, Wayward Pines, and the comedy series High Desert. He noted that as actors age, they are often given more complicated roles, which he enjoys.
Dillon cited milestones in his career, including Drugstore Cowboy, City of Ghosts, and Crash, as major achievements. From 2014 to 2023, Dillon was in a long-term relationship with Italian actress Roberta Mastromichele. With an estimated net worth of $60 million, Dillon has never married or had children and currently resides in Manhattan.
