From 1999 to 2015, Jon Stewart blended humor with politics on the groundbreaking Comedy Central news program, The Daily Show. For many Americans, The Daily Show was how they got their news, and his editorials about real-world issues mixed with comedy made him a household name and a must to watch.
Originally, Stewart got his start as a stand-up comedian and many forget that before he took over hosting duties on The Daily Show, he was an actor in several films. After he started hosting The Daily Show, his acting career diminished but he would still pop up in movies from time to time playing himself. However, despite his short acting filmography, Jon Stewart showed great promise as one.
10 Doogal - 2.9
Doogal is an animated film about a talking dog and his friends that live in an enchanted forest who must stop an evil wizard from starting another ice age. Produced in France, Doogal was dubbed over with American celebrity voices for the US release and Stewart was the voice of the evil wizard, Zeebad.
However, Doogal was panned by critics and audiences. Critics' main bone of contention was that it included too many pop culture references that would soon become dated, as well as lacking any real charm. Stewart has always poked fun at the role himself, and in one interview with critic Roger Ebert, couldn't help but laugh hysterically when describing his character - "a blue spring who wants to freeze the world through ice he shoots out of his mustache."
9 Wishful Thinking - 5.1
In the 1990s, Jon Stewart had a deal with Miramax Pictures and appeared in many of their films, including the romantic comedy Wishful Thinking. The film co-starred Drew Barrymore, Jennifer Beals, and James LeGros and revolved around a couple whose relationship with each other is threatened by the temptations of others, including Henry, charmingly played by Stewart.
The film is indicative of the type of romantic comedies Miramax released in the 1990s. However, unlike some of their other movies, Wishful Thinking didn't go beyond art house movie theaters and, even there, it didn't make waves. While some enjoyed that the film is told through several points of view, as well as for Stewart's performance, many argued that this romantic comedy was neither romantic nor funny.
8 Since You've Been Gone - 5.4
Directed by and starring Friends' David Schwimmer, Since You've Been Gone takes place at a ten-year high school reunion where old friends reunite and discover that while much about them has changed, there are many things that haven't. Jon Stewart didn't have much to do in the film and had a small role as one of the reunion attendees named Todd.
Initially slated for a theatrical release by Miramax, the movie ended up airing instead as a TV movie on ABC. The reason for the switch potentially points to the film's quality as it, unfortunately, lacks good character development, real humor, and, overall, is a disappointing directorial debut from Schwimmer.
7 Mixed Nuts - 5.4
Coming off her box office hit Sleepless In Seattle, writer-director Nora Ephron took a French film and remade it for America as Mixed Nuts. The film is a dark Christmas comedy that mostly takes place in the offices of a suicide prevention hotline. Steve Martin stars as the head of the hotline who tries desperately to keep the financially strapped business afloat.
Jon Stewart has a small role as an unnamed rollerblader alongside Parker Posey and doesn't add much to the story. Unfortunately, the film was critically and commercially unsuccessful, as many felt it was a big disappointment in that it wasn't funny despite the enormously talented cast and crew involved.
6 Death To Smoochy - 6.3
Directed by Danny DeVito, Death To Smoochy is a very dark comedy about the politics behind children's entertainment. The movie stars Robin Williams as hit children's entertainer Rainbow Randolph who, following a scandal, gets replaced by an earnest new star Smoochy (Edward Norton). However, Randolph now seeks revenge on the new scandal-free star.
Currently, Death To Smoochy is Stewart's last live-action fictional role and he plays a traitorous yet funny television executive named Marion who discovers Randolph's replacement, Smoochy. Death To Smoochy received negative reviews for not being the great satire it could have been, however, it has a very large cult following among those who consider it one of the best dark comedies.
5 Big Daddy - 6.4
Ranking for many years as Adam Sandler's most successful movie, Big Daddy stars Sandler as slacker named Sonny who winds up taking care of a small boy that's supposedly the son of his out-of-town roommate Kevin, played by Stewart. Sonny and the boy bond and he becomes more responsible in the process. In the end, Stewart returns and takes custody of his long-lost son.
Big Daddy showcases a lot of heart and, while at times uproariously funny, can also be emotional too. Stewart's character bookends the film but is a great addition to the cast. While the reviews were not great, audiences loved it, and was a huge hit. To this day, Big Daddy is considered one of Sandler's best comedies.
4 The Faculty - 6.5
Written by Scream's Kevin Williamson and directed by Desperado and From Dust Til' Dawn director Robert Rodriguez, Jon Stewart is among the ensemble cast for the teen body snatcher movie, The Faculty. In the film, students discover aliens have taken over the bodies of their teachers.
Stewart plays the hero students' teacher, Mr. Furlong, who after becoming one of the aliens, suffers a gruesome fate that includes his fingers getting cut off and his eye being stabbed with a syringe. Stewart is funny in his brief role and even gets to be scary too. While not a box-office success, it has since become a cult favorite among fans of 1990s teen horror/sci-fi.
3 Half Baked - 6.7
Written by comedians Dave Chappelle and Neal Brennan, Half Baked revolves around three stoners who start a marijuana business in order to raise money to help get their other stoner pal out of jail. The comedy stars Chappelle, Jim Breuer, and Harland Williams.
Jon Stewart has a brief but scene-stealing role as, what the characters call, an "enhancement smoker," someone who thinks everything is better under the influence of marijuana. The scene has become a favorite among fans and has even become a popular meme. Despite negative reviews and a poor box office, Half Baked has also become a cult classic and is considered one of the best stoner comedies of all time.
2 Jay and Silent Bob Strike Back - 6.8
Using his two fan-favorite characters from Clerks and Chasing Amy, stoner duo Jay and Silent Bob, director Kevin Smith created a spin-off adventure for them entitled Jay and Silent Bob Strike Back. The film follows the misadventures of stoner-slackers Jay and Silent Bob as they travel across the country to stop a movie about them from being made.
Jon Stewart has another brief but funny role as Reg Hartner, a news anchor who reports on Jay and Silent Bob's supposed abduction of a monkey and he shares some screentime with Will Ferrell as they dispense with a hilarious double entendre filled conversation that is one of the movie's highlights.
1 Playing By Heart - 7.0
With Playing By Heart, Stewart played his biggest role yet and was a quasi lead in the ensemble romantic comedy alongside Angelina Jolie, Gillian Anderson, and Sean Connery. The film follows four couples, including the lonely theater director and commitment-phobe Meredith (Anderson) as she tries to resist a relationship with lonely architect Trent (Stewart).
Anderson and Stewart have great chemistry together and the film showcases that had The Daily Show never come along, he may have had a great career as a comedic leading man. The film was not a box office hit, but despite good reviews, Stewart never pursued similar lead comedic roles again and instead began his sixteen-year run on The Daily Show the following year where he found enormous success.
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August 01, 2021 at 12:00AM
