Tom Sizemore died Friday after suffering a brain aneurysm earlier this month. One of the defining character actors of the 1990s, his run through the decade saw him work with several of Hollywood’s top filmmakers, including Oliver Stone, Kathryn Bigelow, Michael Mann, Martin Scorsese, Tony Scott and Steven Spielberg. Sizemore’s penchant for playing tough guys made him a mainstay in crime and war films, always bringing color to an ensemble.

After his enviable run through the ’90s, Sizemore remained a reliable actor into the new millennium. He appeared in numerous projects per year, often boosting low-profile films with his star presence. Sizemore also brought to life one of the more enduring characters to emerge from video games, voicing mob boss Sonny Forelli in “Grand Theft Auto: Vice City.” He also made impactful appearances on television shows like “It’s Always Sunny in Philadelphia,” “Hawaii Five-0” and the 2017 Showtime revival of “Twin Peaks.”

Revisit some of Sizemore’s most iconic roles below.