At New York, he attained his first stage experience as a stand-up comedian.
To pursue a career in acting, he left for Los Angeles in the early years of 1980s. During this time, he bagged for himself guest appearances in a couple of television shows, such as ‘Knight Rider’ and ‘The Facts of Life’.
In 1985, he seized his first breakthrough role in the film, ‘back to the Future’. The flick had him playing the role of a bully, Biff Tannen. The role was ironical given the fact that he was the most frequent target of the bullies while at school. He brought in those childhood experiences to highlight reality and develop the character.
In 1986, he starred in two movies, ‘April Fool’s Day’ and ‘Let’s Get Harry’. In 1987, he played the character of Lieutenant Stevenson in the film, ‘Smart Alex’ and in 1988, he was seen portraying the role of a Detroit police officer in the film, ‘Action Jackson’.
In 1989, he starred in the sequel of ‘Back to the Future’ titled, ‘Back to the Future Part II’. In it, he not only played the role of Biff Tannen but of Biff's grandson, Griff Tannen as well.
Year 1990 witnessed the release of the third offering from the ‘Back to the Future’ franchise, titled, ‘back to the Future Part III’. The movie had him reprise the role of Biff Tannen. Furthermore, he also played the character of Biff's great-grandfather, Buford ‘Mad Dog’ Tannen. The role earned him a Saturn Award in the category of Best Supporting Actor.
After the trilogy, the ‘Back to the Future’ franchise came up with an animated series in which he not only reprised his role as Biff but also voiced for various relatives of Tannen as well.
In 1991, he played the character of Al Dalby in the movie, ‘High Strung’. The following year, he gave voice over for several characters such as Tony Zucco in ‘Batman: The Animated Series’, Matt Bluestone in ‘Gargoyles’ and in ‘Borist and Natasha: The Movie’ as additional voices.
He co-starred with Mark Hamill in ‘Wing commander III: Heart of the Tiger’. It was the third offering of the Wing Commander series and had him playing the role of Major Todd ‘Maniac’ Marshall.
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His excellent portrayal earned him a place in the upcoming sequels, ‘Wing Commander IV: The Price of Freedom’, ‘Wing Commander: Prophecy’ where he reprised his role of Major Todd ‘Maniac’ Marshall. He even contributed his voice to the animated series ‘Wing Commander Academy’
In 1994, he starred along with Christopher Lloyd in the comedy, ‘Camp Nowhere’. The same year, he played Billy for ‘Mr White’.
From 1995 until 2000, he starred in three movies, including, ‘Born to be Wild’, ‘The Darn Cat’ and ‘Girl’ playing the characters of Det Lou Greenburg, Officer Melvin and The Ticket Seller respectively.
During this time, his television career also steeped high with him starring in various shows such as, ‘Sabrina, The Teenage Witch’, ‘Andersonville’, ‘Lois & Clark: The New Adventures of Superman’, ‘Duckman’;, ‘Aaahh! Real Monsters’, ‘Fired Up’, ‘Pinky and the Brain’, ‘Men in White’, ‘Zoomates’, ‘Maggie’, ‘Angry Beavers’ and ‘Hughleys’
In 1999, he appeared in the televisions series, ‘Freaks and Greeks’ as McKinley High School's Coach Ben Fredericks. At the same time, he even appeared in an episode of the television show, ‘Pepper Ann’
In 2000, he contributed his voice for the videogame ‘Star Trek Voyager: Elite Force’. His character of Biessman resembled that of ‘Biff Tannen’ of the ‘Back to the Future’ fame, with similar style and personality. However, the former was far more judicious and supportive than the latter. The same year, he gave a voice over for animated production ‘Max Steel’.
In 2003, he starred in the mockumentary, ‘Trial and Error: The Making of Sequestered’. Additionally, he lent his voice for Disney’s ‘Atlantis: Milo Return’. The following year, he provided voice for ‘The SpongeBob SquarePants Movie’
In 2004, he starred along with Marin Mazzie and Jason Danieley in the Pasadena Playhouse production of the musical ‘110 in the Shade’. In it, he played the role of Noah Curry.
In 2005, he released his own comedy album tiled, ‘Tom Wilson Is Funny!’ The following year, he starred in the movie, ‘Larry the Cable Guy: The Health Inspector’ and ‘Zoom’.
In 2007, he returned to television to play the character of Lou, father of Dr House’s patient in the drama, ‘Whatever It Takes’. The following year, he continued his tryst with television starring in the ABC drama ‘Boston Legal’ in the episode ‘Attack of the Xenophobes’, as a former police officer who is charged with murder.
2009 witnessed the release of two of his movies, ‘House Broke’ in which he played the role of Fire Chief Henry Decker and ‘The Informant!’ in which he portrayed the character of Mark Cheviron. The same year, he made a television appearance as himself in ‘Vidiotic’, a comedy pilot on the British channel BBC Three.
In 2011, he hosted a podcast, Big Pop Fun. The show had him share informal chat with friends such as Samm Levine, Blake Clark, Steve Oedekerk, ‘Weird Al’ Yankovic, and more. The same year, he gave voice for the animated movie, ‘Rio’
In 2012 he played the role of Robert Collins in ‘Atlas Shrugged: Part II’. The following year, he starred in the movie, ‘The Heat’ as Captain Frank Woods. He even gave voice to the direct to video film, ‘Tom and Jerry's Giant Adventure’.
As for his television stints, he appeared in an episode of ‘Melissa & Joey’ and in the television series, ‘Zach Stone is Gonna Be Famous’ as Mr Stone. Furthermore, he lent his voice for Dragons: Rider of the Berk’ and ‘Mad’.