Dillon was born Matthew Raymond Dillon, and raised in Mamaroneck, NY. His artistic-leaning family including a father who painted portraits and a pair of uncles who illustrated the famous comic strips "Flash Gordon" and "Blondie." But by the time he was a teen, Dillon seemed unlikely to follow in his family's footsteps and was cultivating an image as a class-cutting back-talker when talent scouts stumbled across him while combing the Horrocks School in search of an unknown talent for the film "Over the Edge" (1979). During his official audition, the 14-year-old made a strong (if abrasive) impression and producers knew they had found the right kid to play a troubled teen in Jonathan Kaplan's powerful film. Following his impressive debut in the indie, he was swiftly cast in two mainstream features, playing a school bully who experiences an eventual comeuppance in "My Bodyguard" (1980) and the object of Kristy McNichol's teen sexual desire in "Little Darlings" (1980). With his budding film career an attractive alternative to suburban high school life, Dillon left school to focus on acting and shot to stardom as the charismatic but confused lead of a trio of teen films adapted from the works of S.E. Hinton, beginning with Tim Hunter's "Tex" (1982). While Francis Ford Coppola's "Rumblefish" was an artful, adult-oriented portrait of a kid from the wrong side of the tracks, his more commercial follow-up "The Outsiders" featuring an astonishing cast of up-and-coming heartthrobs including Tom Cruise, Rob Lowe and Patrick Swayze, transformed Dillon into a teen magazine pinup. While his acting was sometimes clunky, he easily and believably fell into the time-tested persona of a charismatic juvenile delinquent, and in addition, the camera simply loved his moody face. Lightening his image, he starred in Garry Marshall's period comedy "The Flamingo Kid" (1984) where his starring role as a working class Brooklyn kid with upper class envy showed the actor had more range yet to showcase. He re-teamed on screen with "Outsiders" siren Diane Lane in the 1950-set romance "The Big Town" (1987), playing a small town crapshooter whose ambitious move to Chicago finds him caught up in a tangled web of danger and illicit liaisons. After ably holding his own among the all-star cast including Tommy Lee Jones and Bruce Dern, Dillon co-starred opposite pretty boy Andrew McCarthy in the caper "Kansas" (1988), which was forgettable - though Dillon's performance was singled out by reviewers as the film's strength.Under the clear, gritty vision of indie filmmaker Gus Van Sant, Dillon was reborn with "Drugstore Cowboy" (1989), which shed Dillon's Hollywood version of seedy characters in favor of a toothy and realistic starring role as a drug addicted thief nearing the end of his run. For his assured, mature performance (opposite Kelly Lynch as his wife), Dillon won a Best Lead Actor honor from the Independent Spirit Awards and finally left his reputation as a 1980s heartthrob in the dust. "A Kiss Before Dying" (1991), a mainstream thriller, failed at the box office but earned Dillon another round of accolades for a subtle performance, and he followed up with a supporting role in Cameron Crowe's generation X chronicle "Singles" (1992), where he gave an amusing turn as a dim-witted, flannel clad Seattle rocker. He proved convincing as a working-class Italian-American with dreams of owning a bowling alley in the light romantic comedy "Mr. Wonderful" (1993), and reunited with director Tim Hunter to play a disturbed man who is befriended by a homeless Danny Glover in "The Saint of Fort Washington" (1993), which received mixed reviews.Van Sant tapped Dillon for a supporting role as the happily suburban (and doomed) husband of a fiercely ambitious weather girl (Nicole Kidman) in the sharply humorous "To Die For" (1995), and the same year displayed a winning chemistry with Anne Parillaud in "Frankie Starlight." In another indie success, he appeared in the praised ensemble comedy "Beautiful Girls" (1996) and played a 1960s record producer in Allison Anders' pop music portrait "Grace of My Heart" (1996). With his hilarious role as a self-impressed actor who unwittingly outs his closeted gay high school teacher (Kevin Kline) at the Academy Awards in "In & Out" (1997), Dillon entered the new realm of successful mainstream comedies. His follow-up performance in the Farrelly Brothers' mega blockbuster "There's Something About Mary" (1998), however, really caused audiences to rediscover Dillon, who was praised for his comic performance as the cartoonish, mustachi d private dick who stalks, then falls in love with the woman he was hired to track down (Cameron Diaz). Further fueling the publicity machine of the gross-out hit, Dillon and Diaz became involved in a long-term romance - one of the few ever made public by the private star who had, in the past, only been linked with frequent co-star Diane Lane.Back in the spotlight, Dillon was cast as a popular guidance counselor wrongly accused of rape in the sexy, campy thriller "Wild Things" (1998) opposite Neve Campbell, Denise Richards and Kevin Bacon. In a rare move to television Dillon directed an episode of HBO's gritty prison drama "Oz" (1997-2003) and was not seen onscreen again until 2001, when he gave a "Mary"-reminiscent performance as a macho sleazeball in the comedy "One Night at McCool's." However even a star-studded cast including Michael Douglas, John Goodman and Liv Tyler failed to turn the film's promising conceit into a solid comedy. In 2002, Dillon unveiled his first feature filmmaking effort, "City of Ghosts," which followed the story of con man who travels to Cambodia to get his share from an insurance scam but finds himself caught in a much more dangerous situation. From his ambitious writing and directing debut, Dillon went on to star in the Sundance-screened caper comedy "Employee of the Month" (2004). Dillon's career experienced another upturn with an Oscar-nominated supporting performance in the racially charged, multi-plot drama "Crash" (2005). Playing an angry LAPD patrol officer whose frustrations at home lead him to act out on the job, Dillon delivered an unflinching, complex performance that stood out even among the film's top-flight acting ensemble. In a display of unbridled versatility, Dillon played a NASCAR champ who gets beat racing a lovable, animated Volkswagen Bug in the Disney blockbuster "Herbie: Fully Loaded" (2005). "You Me and Dupree" (2005), a predictable romantic comedy where Dillon essayed the straight man whose bachelor buddy moves in with him and his new bride (Kate Hudson), proved just as big a hit with movieg rs. He returned to indie drama with "Factotum" (2005), starring in the film adaptation of one of Charles Bukowski's autobiographical chronicles of drinking, gambling, women and p try. Dillon's dark, deadpan portrayal of the cult figure was well received, and he proved he had still more surprising characterizations in store with his 2008 portrayal of a federal prosecutor deciding the case of a newspaper reporter (Kate Beckinsale) who outs the identity of a CIA operative in the current-events inspired "Nothing But the Truth."