Kevin Dillon made his debut in the 1983 television film ‘No Big Deal’ where he played the role of ‘Arnold Norberry.’ He was next seen in the 1985 American drama film ‘Heaven Help Us’ directed by Michael Dinner. The film received a mixed response from critics and was a commercial failure. He went on to star in films like ‘The Delta Force’ (1986), ‘Platoon’ (1986), ‘Dear America: Letters Home from Vietnam’ (1987), and ‘Remote Control’ (1988). In 1988, he starred as ‘J.J. Merrill’ in the adventure film ‘The Rescue’ directed by Ferdinand Fairfax. The film was panned by critics and failed to perform at the box office. However, Dillon earned praise for his performance and earned a ‘Young Artist Award’ nomination. He bagged another ‘Young Artist Award’ nomination for his performance as ‘Sam’ in the 1989 drama film ‘Immediate Family’ directed by Jonathan Kaplan.
In 1993, he made his television debut in the Episode: "House of Horror" of the American horror anthology television series ‘Tales from the Crypt.’ In 1998, he joined the cast of the American police procedural drama television series ‘NYPD Blue’ created by Steven Bochco and David Milch. He played the role of ‘Officer Neil Baker’ and appeared in 3 episodes of the series. He next appeared in the American comedy-drama television series ‘That’s Life’ in 2000. The show aired 36 episodes and went off-air in 2002. After making brief appearances in television series like ‘24’ (2003), ‘Karen Sisco’ (2003), and ‘Maple Ave’ (2003), Dillon got his breakthrough role as Johnny "Drama" Chase in the American comedy-drama television series ‘Entourage’ in 2004. The series ran for 7 years and aired its final episode in 2011. Dillon also earned a ‘Golden Globe Award’ 3 ‘Primetime Emmy Award’ nominations for his performance in the series.
The year 2013 saw the release of the Canadian psychological thriller film ‘Compulsion’ where Dillon was seen playing the role of ‘Fred.’ The film received mixed reviews from critics. He reprised his role as Johnny "Drama" Chase in the 2015 American comedy film ‘Entourage’ directed by Doug Ellin. The film received mostly negative reviews and was a box office disappointment. He next appeared in films like ‘Underdogs’ (2015), ‘Dirt’ (2018), ‘Brothers in Arms’ (2018), and ‘The Buddy Games’ (2019). He was last seen in the Episode: "Model Kid" of the American horror anthology streaming television series ‘Creepshow’ (2021). Dillon is all set to appear in the upcoming biographical historical drama film ‘Reagan’ where he will portray ‘Jack L. Warner.’ He will also be seen in the upcoming American action-heist film ‘A Day to Die.’
