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).