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Sizemore appeared alongside the Insane Clown Posse in the comedy film Big Money Rustlas (2010) and the drama 513 with Michael Madsen.
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Sizemore starred alongside martial arts actor Mark Dacascos in the action movie Shadows in Paradise (2010), followed by an appearance as a trucker in an episode of It's Always Sunny in Philadelphia. Sizemore starred in the indie horror film Murder 101 (2014) and co-starred with Kyra Sedgwick and Vincent D'Onofrio in the comedy-drama film Chlorine (2013).
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He went on to appear in five episodes of the television series Crash (2008–2009) with Dennis Hopper and the comedy film Super Capers (2009). He was highly prolific that year, starring in The Last Lullaby (2008), The Flyboys (2008) with Stephen Baldwin, action film Stiletto (2008) with Tom Berenger and Michael Biehn, drama film Toxic (2008) with Costas Mandylor, and the Canadian drama A Broken Life (2008) with Ving Rhames. Sizemore performed in two films that screened at the 2008 Sundance Film Festival, Red (2008) and American Son (2008).
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In the same year, the actor starred in the Indie drama film Oranges (2007) with Tom Arnold and Jill Hennessy, which was directed by Syrian director and producer Joseph Merhi. The series also covered an ongoing legal appeal of his conviction for an assault of former Hollywood madam Heidi Fleiss.
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The next year, television network VH1 aired a six-episode reality TV series called Shooting Sizemore (2007), depicting the actor's life as he struggled to regain his career in the midst of battling long-standing addictions to methamphetamine and heroin. He went on to a leading role in the action/thriller film Splinter (2006) with Edward James Olmos. That same year, he starred in The Genius Club (2006), playing a terrorist who taunts seven geniuses into solving the world's problems in one night. He appeared prominently in the Mel Gibson-produced Paparazzi (2004) and played an undercover cop in Swindle (2006), opposite Sherilyn Fenn. He also starred in the well-reviewed but short-lived television drama series Robbery Homicide Division (2001) it was cancelled midway through its first season. Sizemore starred in Ticker (2001), an action film directed by Albert Pyun, with Steven Seagal and Dennis Hopper. He had a voice role as Sonny Forelli in the video game Grand Theft Auto: Vice City. In the early 2000s, Sizemore appeared in actions films such as Pearl Harbor (2001), starring Ben Affleck, and Ridley Scott's Black Hawk Down (2001). Saving Private Ryan (1998) has proven to be his most commercially successful project to date, bringing in $217,000,000 at the box office. Sizemore continued to play leading and character parts in many films, notably Devil in a Blue Dress (1995), Bringing Out the Dead (1999) and Witness Protection (1999). Sizemore had a recurring role on the television series China Beach (1988–1991) as an enlisted man named Vinnie who was in love with Dana Delany's character.
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Sizemore's first major leading role was as Vincent D'Agosta in The Relic (1997). Ī succession of well-received supporting parts followed, notably including his portrayal of Michael Cheritto in the heist film Heat (1995). For his performance in Heart and Souls (1993), he was nominated for the Saturn Award for Best Supporting Actor. Sizemore starred in the independent drama film Love Is Like That (1993) with actress and model Pamela Gidley and had a supporting role in Kevin Costner's Wyatt Earp (1994) as Bat Masterson. Other early roles included Lock Up (1989), Harley Davidson and the Marlboro Man (1991), Point Break (1991), True Romance (1993), Natural Born Killers (1994) and Strange Days (1995). One of Sizemore's earliest film appearances was in Oliver Stone's Born on the Fourth of July (1989). JSTOR ( January 2016) ( Learn how and when to remove this template message).Contentious material about living persons that is unsourced or poorly sourced must be removed immediately, especially if potentially libelous or harmful. This section of a biography of a living person needs additional citations for verification.