As his career progressed, he took on more diverse roles, starring in critically acclaimed films such as Drugstore Cowboy (1989), Singles (1992), There's Something About Mary (1998), and Crash (2004), for which he received an Academy Award nomination for Best Supporting Actor.
Beyond acting, Dillon made his directorial debut with City of Ghosts (2002) and has continued to work in film and television, including starring in the series Wayward Pines (2015). His career spans decades, showcasing his versatility in both dramatic and comedic roles.