Over the course of the past 30-some-odd years, Jason Lee has gone from an up-and-coming skateboarder with boundless charisma to one of Kevin Smith’s most prolific collaborators to an actor who can hold his own in just about any role that is thrown his way. Stoner comedies, political thrillers, coming-of-age dramas about rock-and-roll bands on the rise, nothing is unthinkable for the versatile actor.
But, with so many performances throughout his career, settling on the best Jason Lee movies and TV shows isn’t the easiest of tasks, especially when you have to settle on 10 of the best examples of his work. We’re up to the challenge, though, and have put together this little list of great options and where you can find them streaming and by other means.
Almost Famous (2000)
Lying about his age and qualifications, 15-year-old aspiring rock reporter William Miller (Patrick Fugit) is hired by Rolling Stone magazine to go on tour with up-and-coming outfit Stillwater, which is going through an identity crisis as the group experiences their first real taste of success in the early 1970s.
Loosely based on writer/director Cameron Crowe’s own experience, and one of the best movies based on true stories, Almost Famous is a love-letter to the bands, music critics, and groupies of the era, creating an enchanting experience that is both endearing and honest in its approach to the subject matter. Although Stillwater guitarist Russell Hammond (Billy Crudup) takes up much of the screen-time, frontman Jeff Bebe (Jason Lee) is an incredible character who gives the actor a chance to show his range as a musician afraid of getting too big too fast.
My Name Is Earl (2005 - 2009)
After learning about the concept of karma following a seemingly random accident that cost him a winning lottery ticket, Earl Hickey (Jason Lee) goes on an odyssey that sees him make a list of his bad deeds and set out to right the wrongs of his life and make up for all the pain, suffering, and misfortune he brought into the lives of his family, friends, and anyone else who’s crossed his path.
The My Name Is Earl cast featured a who’s who of talent from the early 2000s that received a ton of praise throughout its initial run, with most of that turned towards Jason Lee. Today, some may still picture the small-time crook with a heart of gold whenever the actor’s name comes up. In his portrayal of the character, Lee was able to find humor, honesty, and humility despite playing a down-on-his-luck criminal.
Chasing Amy (1997)
Upon meeting fellow comic book artist Alyssa Jones (Joey Lauren Adams), Holden McNeil (Ben Affleck) falls head over heels for her. But, there is just one thing standing in between Holden and his crush: Alyssa is a lesbian. Despite that, Holden does everything he can to make it work, even if it means breaking the bond shared with his best friend and creative partner, Banky Edwards (Jason Lee).
One of the most complicated of Kevin Smith’s movies, Chasing Amy (specifically the character of Banky Edwards) has a strange and outdated outlook on the LGBTQ+ community that is rather offensive at times. If you can look past that, you see a distressed and confused man who is doing anything he can to preserve the relationship he has with his best friend, even if that means upsetting everyone else in this romantic comedy.
The Incredibles (2004)
Longing for the days before all superheroes were banned by the government, Mr. Incredible (Craig T. Nelson) gets his second shot at superstardom when he is forced to take on an evil robot. But upon arriving on the far-away island to vanquish the evil creation, Mr. Incredible, and the rest of his family, come in contact with a new, more powerful foe.
One of the best Pixar films, The Incredibles is full of fun and heart, which is one of the reasons it won two Academy Awards following its release. The other? Well, it could have something to do with the outstanding The Incredibles cast, which also included Holly Hunter, Samuel L. Jackson, and Jason Lee, who portrayed the superheroes’ overzealous superfan who becomes Syndrome, a powerful and obsessive villain hellbent on destruction.
After being dumped by their girlfriends, T.S. Quint (Jeremy London) and Brodie Bruce (Jason Lee) do what any guys would do: they go to the mall. While at the local center of commerce, the two friends encounter not only their ex-girlfriends, but also just about anyone and everyone else they wouldn’t want to run into in their current state.
If you want to know why Mallrats is one of Jason Lee’s best movies, just start playing it and then skip to some random spot in the 90-minute film (123-minutes if you’re watching the extended version). You are guaranteed to see everything from a conversation where Brody explains why Superman and Lois Lane aren’t a good match to a run-in with Stan Lee himself (the late comic creator’s Captain Marvel cameo makes this scene even better).
Jay And Silent Bob Strike Back (2001)
When Jay (Jason Mewes) and Silent Bob (Kevin Smith) discover that not only are their comic book likenesses, Bluntman and Chronic, are being turned into a feature film, but the pair won’t receive any royalties due to a shady business deal, they go on a cross-country trip to prevent the project from ever seeing the light of day.
Jay and Silent Bob Strike Back is absolutely bonkers, even by Kevin Smith’s standards. This 2001 stoner comedy not only features the cast from Smith’s previous films reprising their roles, it also sees some actors, like Jason Lee, show up in two completely different roles. First, there’s Brodie Bruce, who tells the heroes about the whole film adaptation, and then Banky Edwards shows up in one of the best scenes of the movie, the one where Bob finally speaks and lays it all out.
Enemy of the State (1998)
When Thomas Reynolds (Jon Voight) realizes there is a video showing the assassination of a congressman, the corrupt NSA official does everything, and kills everyone in his way, to get ahold of the evidence. He soon turns his attention to Robert Dean (Will Smith), a Washington, D.C. lawyer who ends up with the footage after a run-in with an old college buddy.
The main storyline in Tony Scott’s 1998 political thriller Enemy of the State wouldn’t get off the ground if were not for Jason Lee’s Daniel Zavitz, the researcher who first catches a glimpse of the murder when watching migratory birds on a fixed camera. He’s only in the movie for a hot minute, but Lee shows incredible range with his portrayal of a terrified man caught in the middle of a massive scandal.
Vanilla Sky (2001)
David Aames (Tom Cruise) is a young publishing magnate who has everything he thinks he needs in life: good looks, personal and professional success, and beautiful women who want to be with him. When a terrible accident takes nearly everything away from him, David begins to question reality while also trying to make sense of it.
Cameron Crowe’s mind-bending 2001 drama, Vanilla Sky, is incredibly ambitious with its sprawling narrative and eye-catching visuals, but at the center of the story is the drama between its main characters, who are played by Cruise, Penelope Cruz, Cameron Diaz, and Jason Lee, who plays Cruise’s on-screen best friend, Brian Shelby. The great thing about Brian is the fact you never really know where he stands and if he’s a good or bad friend, which is due to both Crowe’s writing and Lee’s dynamic performance.
Monster House (2006)
After failing to convince his parents (and other neighbors) to help, D.J. Walters (Mitchel Musso) calls on his neighborhood friends to get to the bottom of the mystery surrounding the creepy house on his street that is supposedly possessed, in the well-received Monster House.
Along the way, the trio come in contact with various people who have a history with the house and its spirit habitant, including Bones (Jason Lee), D.J.’s babysitter’s cruel boyfriend. Although not in the movie all that long, Lee’s portrayal of a snot-nosed teenager having fun at others’ expense is incredible and helps add another level to the fairly creepy movie.
Raising Hope (2010 - 2013)
When the mother of his child (a notorious serial killer) is sentenced to death, James “Jimmy” Chance (Lucas Neff) becomes the baby’s primary caretaker. Not knowing what to do with a baby to keep it alive, the mild-mannered 20-something enlists his family, who are equally unqualified, to help out.
In addition to the main Chance family, which was portrayed by Martha Plimpton, Garret Dillahunt, and Cloris Leachman, Raising Hope also featured a number of other characters, some of which came from series creator Greg Garcia’s previous shows. One of these guest stars is none other than Jason Lee, who played an out-of-touch rock singer named Smokey Floyd. Lee shows up in a few episodes, and captures that same magic that made his turn on My Name Is Earl so good, but just not as wholesome as his other major TV role.
Stream Raising Hope on Hulu.
Buy Raising Hope on Amazon.
As you can see, Jason Lee has done a little bit of everything since breaking out as one of Hollywood’s go-to comedic actors 30 years ago. Though some of his all-time great movies, like Dogma and his various skate tapes, are hard to find, there’s a good chance we’ll soon see Lee again on the 2022 new movies schedule.
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Philip grew up in Louisiana (not New Orleans) before moving to St. Louis after graduating from Louisiana State University-Shreveport. When he's not writing about movies or television, Philip can be found being chased by his three kids, telling his dogs to stop barking at the mailman, or chatting about professional wrestling to his wife. Writing gigs with school newspapers, multiple daily newspapers, and other varied job experiences led him to this point where he actually gets to write about movies, shows, wrestling, and documentaries (which is a huge win in his eyes). If the stars properly align, he will talk about For Love Of The Game being the best baseball movie of all time.