Jason Lee’s best movies and TV show roles highlight the career of an actor who has been popular in a number of notable projects but whose talents are still sorely underrated. Lee started his career as a professional skateboarder, earning a name for himself as the sport was picking up mainstream popularity in the early 1990s. While that path led to him getting some movie roles, he proved to have a natural talent on screen with a likable charm, strong comedic sense, and an easygoing demeanor.
It didn’t take long for Lee to become known more for his acting than his skateboarding, thanks largely to the fact that he was welcomed into Kevin Smith’s universe of recurring actors. However, Lee also established a strong career for himself in his own right with projects that showcased his versatility while also elevating him to another level of stardom. While he might never have been one of the biggest lead actors in the business, a look at Lee’s best movies and shows highlights all the great work he’s done.
10 Jay and Silent Bob Strike Back (2001)
As Brodie Bruce / Banky Edwards
Jay and Silent Bob Strike Back RComedy Where to Watch
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Jay and Silent Bob Strike Back is a 2001 comedy film directed by Kevin Smith, starring Jason Mewes and Kevin Smith as the titular characters. The plot follows the duo as they embark on a cross-country journey to Hollywood to prevent a film based on their likenesses from being made. Along the way, they encounter various comedic misadventures and cameos from the View Askewniverse.
Director Kevin Smith Release Date August 24, 2001 Cast Jason Mewes , Kevin Smith , Harley Quinn Smith , Ever Carradine Runtime 104 minutes
Kevin Smith’s Viewaskewniverse movies were tentatively tied together mostly through the appearance of the characters of Jay and Silent Bob. However, while these characters were largely supporting players in other stories, they were thrust into the spotlight in Jay and Silent Bob Strike Back which served as a true melding of all of Smith’s movies to that point. As such, Jason Lee reprises various characters he has played in the past.
The movie follows Jay and Silent Bob as they discover that the comic book characters that are based on them, Bluntman and Chronic, are getting their own live-action movie without Jay and Silent Bob’s approval. The road trip adventure finds the iconic duo first learning about the movie from Lee’s Mallrats character Brodie Bruce and subsequently going to confront the comic book creator, Lee’s Chasing Amy character Banky Edwards. While Jay and Silent Bob Strike Back is best enjoyed by hardcore fans of Smith’s work, it is a funny adventure with some terrific cameos.
9 Vanilla Sky (2001)
As Brian Shelby
Vanilla Sky 1
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Vanilla Sky is a psychological thriller directed by Cameron Crowe, featuring Tom Cruise as a wealthy publishing magnate named David Aames. Released in 2001, the film explores themes of identity, reality, and the consequences of one’s actions, intertwined with surreal events. Co-starring Penélope Cruz and Cameron Diaz, the film is known for its intricate narrative and engaging performances. Vanilla Sky is a remake of the Spanish film “Open Your Eyes.”
Director Cameron Crowe Release Date December 14, 2001 Cast Tom Cruise , Penelope Cruz , Kurt Russell , Jason Lee , Noah Taylor , Cameron Diaz Runtime 136 Minutes
Jason Lee got to work with some big-name talents in a movie that was outside his typical fare. Vanilla Sky is Cameron Crowe’s remake of the 1997 Spanish film Open Your Eyes and reunites Crowe with his Jerry Maguire leading man Tom Cruise. The movie stars Cruise as a self-centered and vain publishing magnate who finds himself falling for a mysterious woman only for his perfect life to unravel as he begins to question his own reality.
The supporting cast includes the likes of Cameron Diaz, Penelope Cruz, Kurt Russell, Michael Shannon, and Lee in a standout role as Cruise’s best friend, Brian. He holds his own against Cruise in some memorable scenes in which their friendship is one of the things that begins falling apart. The movie is very different from Jerry Maguire and critics did not vibe with the surreal ride when it was first released. However, Vanilla Sky has since found more appreciation for its wild and complex journey with some outstanding performances.
8 Mallrats (1995)
As Brodie Bruce
Mallrats 1
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Mallrats is the second film in Kevin Smith’s View Askewniverse and a prequel to Clerks, focusing on two friends who bond at a mall after being dumped by their girlfriends. The film didn’t perform well at the box office but has since become a cult classic and one of the most notable films in Smith’s portfolio.
Director Kevin Smith Release Date October 20, 1995 Cast Jason Lee , Kevin Smith , Jeremy London , Claire Forlani , Jason Mewes , Joey Lauren Adams , Shannen Doherty , Ben Affleck Runtime 94 minutes
Jason Lee’s first collaboration with Kevin Smith also served as Lee’s first real movie role. The ’90s comedy Mallrats follows T.S. Quint (Jeremy London) and Brodie Bruce (Lee), two young men who have both recently been dumped by their girlfriends attempting to get past their troubles and get revenge during a day at the mall. There, they run into a variety of colorful characters, including mall security, obsessive shoppers, and, of course, Jay and Silent Bob.
Lee quickly cements himself as a charming and funny young star, showing particular talent for delivering Smith’s fast-paced and pop culture-heavy dialogue. He has one particularly great standout scene when comic book lover Brodie runs into Stan Lee himself, who imparts some wisdom about love. The movie itself is a funny look at Smith’s take on a mainstream ’90s comedy with a strong supporting cast, including Michael Rooker, Shannen Doherty, and Ben Affleck in his first Kevin Smith movie.
7 Enemy Of The State (1998)
As Daniel Zavitz
Enemy Of The State RActionDramaThriller
Enemy of the State is a political thriller directed by Tony Scott, featuring Will Smith as Robert Dean, a lawyer unwittingly thrust into a covert government conspiracy after obtaining evidence of a politically motivated murder. Gene Hackman co-stars as an ex-NSA operative who aids Dean in navigating the perilous landscape of surveillance and corruption. The film examines the far-reaching implications of government overreach and personal privacy invasion.
Director Tony Scott Release Date November 20, 1998 Cast Will Smith , Gene Hackman , Jon Voight , Regina King , Loren Dean Runtime 132 Minutes
Jason Lee is not an actor who has appeared in many action movies, but he fits well into Tony Scott’s modern espionage thriller Enemy of the State. The action movie stars Will Smith as a family man and lawyer who becomes targeted by a rogue covert ops group that is trying to locate a damning videotape they think Smith has. As his reputation is torn apart and his ideal life is dismantled, he finds help from a mysterious surveillance expert (Gene Hackman).
Lee has a small but pivotal role in the movie as Daniel Zavitz, the man who kicks off the fast-paced story when he accidentally records a political assassination and inadvertently implicates Smith’s mild-mannered hero. Lee’s short performance shows the intensity he can bring to a role like this, something that is not seen in many of his other projects.
6 Monster House (2006)
As Bones
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No adults believe it when three teenagers tell them that there is a house in their neighborhood that is a dangerous creature. With Halloween approaching, they have to find a way to destroy the house before it harms innocent children.
Director Gil Kenan Release Date July 21, 2006 Cast Spencer Locke , Sam Lerner , Catherine O’Hara , Fred Willard , Maggie Gyllenhaal Runtime 91 minutes
While not Jason Lee’s most memorable animated project, Monster House has become a cult favorite for audiences of all ages to enjoy during the Halloween season. The Amblin movie follows a group of youngsters in a quiet suburban neighborhood who become obsessed with the creepy old house on their block, eventually coming to learn that the house is an actual monster itself. Lee has a voice role as Bones, a dim-witted teen who is one of the house’s first victims.
The movie does a great job capturing that Amblin charm that mixes young childhood adventures with some genuinely creepy elements. In that sense, it feels like a more family-friendly animated version of Stranger Things. Lee is also part of a strong voice cast that includes Steve Buscemi, Maggie Gyllenhaal, and Catherine O’Hara. It is a perfect introductory movie for young fans looking for something with a creepy vibe without being too intense.
5 Dogma (1999)
As Azrael
Dogma RDramaFantasyAdventureComedy
Dogma is a 1999 comedy that revolves around two fallen angels, Bartleby and Loki, who try to get back to Heaven after getting thrown out by God. It is part director Kevin Smith’s the View Askewniverse, and it counts with an ensemble cast that includes Ben Affleck, Matt Damon, Alan Rickman, Salma Hayek, Chris Rock, Linda Fiorentino, Jason Lee, and Jason Mewes.
Director Kevin Smith Release Date November 12, 1999 Cast Ben Affleck , Chris Rock , Matt Damon , Alan Rickman , Linda Fiorentino Runtime 130 minutes See at Walmart
While Kevin Smith wisely casts Jason Lee in likable comedic roles in many of their movies together, he found an interesting new way to cast Lee in Dogma. The fantasy comedy is Smith’s most ambitious and bold movie, resulting in one of his best. Ben Affleck and Matt Damon star as two angels who have been cast out of heaven only to discover a loophole that would allow them to return. However, a band of unlikely heroes (including Jay and Silent Bob) are tasked with stopping the angels as their plan will bring about the end of all things.
Lee plays the first villainous role of his career as the demon Azrael, who has his own plans regarding the mission. Lee mixes his usual charm and sense of humor with some very effective sinister edge and menace, resulting in one of the best performances in the movie. Smith’s writing is also particularly sharp, creating a fascinating mythos and clever ideas related to Catholicism. It makes for a very rare epic R-rated fantasy comedy.
4 Chasing Amy (1997)
As Banky Edwards
Chasing Amy 1
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Chasing Amy is a romantic comedy-drama film by writer-director Kevin Smith. Following the viewpoint of comic artist Holden McNeil (Ben Affleck), the movie focuses on his hopeless romantic attachment to a fellow comic artist who happens to be a lesbian – and his best friend’s attempts at voicing his disapproval. The film explores the complex layers of love and what forms it takes.
Director Kevin Smith Release Date April 4, 1997 Cast Ben Affleck , Joey Lauren Adams , Jason Lee , Dwight Ewell , Jason Mewes Runtime 93 Minutes
Jason Lee’s best collaboration with Kevin Smith earned both of them some of the best reviews of their respective careers. Chasing Amy is Smith’s unique take on a rom-com that stars Ben Affleck as Holden, a comic book artist who falls for a woman named Alyssa (Joey Lauren Adams) only to find out she is gay. However, though he attempts to carry on with their relationship as friends, he cannot separate the romantic feelings that he feels for her.
Lee won the Independent Spirit Award for his performance as Banky, Holden’s obnoxious and self-centered friend who is constantly butting in on his relationship with Alyssa, leading to the awkward third act. Chasing Amy‘s ending continues to be controversial years later, with many suggesting the movie and its message has aged poorly. However, the humor and the performances remain the movie’s selling point, showing that Smith was capable of some real depth to his writing.
3 My Name Is Earl (2005-2009)
As Earl Hickey
My Name Is Earl 3
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My Name is Earl is an NBC comedy series that ran between 2005 and 2009. The series centers on Earl Hickey, a resident of rural Camden, who uses his wealth to do good deeds around his town after recovering his stolen $100,000 lottery ticket. The series stars Jason Lee alongside Ethan Suplee, Jaime Pressly, Nadine Velazquez, and Eddie Steeples.
Release Date September 20, 2005 Cast Ethan Suplee , Jason Lee Seasons 4
While Jason Lee has had a lot of great projects throughout his career, My Name Is Earl is likely the one that he is best known for. The sitcom was a hilarious vehicle for Lee’s easygoing charm and likable everyman quality. He stars as Earl, a thirtysomething self-centered slacker who wins the lottery only to promptly lose his winning ticket. Seeing it as a sign of karmic justice for all the bad things he has done, Earl makes a list of all his bad deeds and sets out to make them right.
The clever premise allowed for Earl and the rest of the wonderful My Name Is Earl cast to have fun with their weekly adventures righting the wrongs of the past. While the show did eventually grow a little stale with the repetitive formula, it still delivered charm and Lee made for an excellent leading man. He earned two Golden Globe nominations and plenty of praise for the hit series.
2 Almost Famous (2000)
As Jeff Bebe
Almost Famous pg-13DramaDocumentary Where to Watch
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Almost Famous is a Drama and Comedy film written and directed by Cameron Crowe. The 2000 release stars Kate Hudson, Patrick Fugit, Frances McDormand, and Billy Crudup. Although the film didn’t do well at the box office, it became an instant cult classic as it chronicles the life of a child prodigy named William Miller as he aspires to be a Rock Music journalist for Rolling Stone.
Director Cameron Crowe Release Date September 15, 2000 Cast Billy Crudup , Frances McDormand , Kate Hudson , Jason Lee , Patrick Fugit , Zooey Deschanel Runtime 122minutes
Jason Lee’s charismatic presence makes him very believable as a rockstar, a role he fits nicely into Cameron Crowe’s ode to rock music. Almost Famous stars Patrick Fugit as a young teen aspiring to be a rock and roll journalist in the early 1970s who joins an up-and-coming rock band while they are on tour. While getting to know the band and their inner struggles, he also falls for the musicians’ muse, Penny Lane (Kate Hudson).
Lee has a great role as part of the larger ensemble as Jeff Bebe, the band’s lead singer, who is passionate about the music they are making while also being overly sensitive about how they come across in the media. Lee finds a fine line to walk between being an engrossing larger-than-life artist and a pretentious jerk who doesn’t really believe what he is spouting about artistic integrity. The entire movie is a compelling excuse to hang out in this world with fun characters and vibrant energy.
1 The Incredibles (2004)
As Syndrome
The Incredibles 15
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Pixar’s The Incredibles tells the story of a super-family forced to conceal their powers. Years after superheroes were outlawed, the superpowered Parr family live a normal life. However, after his secret vigilante work uncovers a conspiracy that points to the rise of a new supervillain, Mr. Incredible must rely on the help of his wife Elastigirl and their children, Violet and Dash, to save the world from the evil Syndrome.
Director Brad Bird Release Date November 5, 2004 Cast Sarah Vowell , Samuel L. Jackson , Craig T. Nelson , Spencer Fox , Holly Hunter , Jason Lee Runtime 115 minutes
Despite Jason Lee’s best role being an animated one, it is no less impressive the performance that he gives in The Incredibles. Brad Bird directed this Pixar take on the superhero genre that takes a look at a world populated by superpowered vigilantes until they are outlawed. The story then focuses on a superpowered family living a quiet life under new identities until the father, Mr. Incredible, gets the opportunity to become a hero once again.
Lee makes for the best Pixar villain and one of the best Disney villains of all timeas Syndrome, a mad scientist who feels revenge on superpowered people for making him feel inferior. Lee is dastardly and menacing, but he is also funny and original. His character is a testament to the clever approach the movie takes with a superhero story, finding new ways to comment on old tropes. It also features some of the best action sequences in a superhero movie, rivaling anything Marvel and DC have put on the big screen.