With his career spanning more than twenty years of absolute comedy genius, anyone would have thought Ben Stiller was going to stay in his comfort zones of usual funny roles, and occasional impressions of tropes that not many people are able to effectively do. But Stiller has proven otherwise.
In fact, early on in his career, he proved his talent in other fields by solidly directing feature films, a task that not many people know about. Decades after, the industry trusts him enough to give him projects where he keeps a low profile and still manages to make great films and TV shows. The best thing? He doesn't always stick to comedy.
However, Stiller is one of those faces that can easily make you laugh with subtle management of physical comedy that's usually reserved for embarrassing characters played by actors that aren't afraid of making fools out of themselves. But make no mistake, it isn't the only genre he can be good in. We got the Rotten Tomatoes ranking of his best performances to prove it.
20 Reality Bites (1994) - 63%
In Stiller's debut as a director, Reality Bites, he plays Michael Grates, a snobby executive dating Lelaina and who represents the antithesis of the film's rebellious, grunge-like spirit that made it a cultural staple when it was released in 1994. This one is much better and more interesting than its 63% rating.
19 Zoolander (2001) - 64%
In 2001, Stiller was already a comedy icon that showed up several times each year in funny films. But when he made Zoolander, the film gave him a notable visibility that would seldom repeat in his further career. In the film, Stiller plays Derek Zoolander, the slow-witted model who will try to save his industry while questioning himself and his declining career. Stiller was also the director of the film.
18 Madagascar: Escape 2 Africa (2008) - 64%
In the Madagascar franchise, Stiller plays Alex, the lion who performs on a daily basis at the Central Park Zoo. In Madagascar: Escape 2 Africa, Stiller's Alex heads back to Africa with his friends to reconnect with his roots as he discovers this is where he originally came from. As with every film of this franchise, it's all about the dynamics of four inseparable friends who decide to do everything together.
17 Zero Effect (1998) - 66%
In 1998, Stiller was still building his career. The foundations were not very clear, as shown in his performance in Jake Kasdan's Zero Effect, a comedy that constantly steps into the mystery territory and restrains Stiller to work as a secondary character working under a script that honestly isn't very good. Fortunately, this was the year when he starred in the film that would drastically change his career. Hint: the one with the zipper.
16 Tower Heist (2011) - 67%
Brett Ratner's Tower Heist stars Stiller, alongside an ensemble of actors in the pure style of an "Ocean's something" film. Casey Affleck, Alan Alda, Matthew Broderick, and Eddie Murphy are only some of the names in the film about a heist carried out by vengeful victims of a Ponzi scheme. Stiller and Murphy are an unbeatable formula in whatever film you put them in and Tower Heist proves that.
15 Keeping the Faith (2000) - 69%
The 2000 film Keeping the Faith directed by one of its stars, Edward Norton, is the story of two best friends who fall in love with the same girl. The thing is Brian (Norton) and Jake (Stiller), are a priest and a rabbi, respectively. Their religious values clash when they reveal their intentions to each other and the girl (Jenna Elfman). This is a forgettable romantic comedy that didn't do much for Stiller as that same year would see him performing in Meet the Parents, the one film that mattered.
14 Dodgeball: A True Underdog Story (2004) - 71%
There's only one thing better than Stiller's mustache in Dodgeball: A True Underdog Story; his character being rejected by a beautiful girl. In Dodgeball, Stiller plays White Goodman the short but strong adversary to LaFleur's pack of underdogs. It's incredible that Stiller was able to perform this iconic role in a year that saw him appear in six mainstream films, even if one of them was only a cameo appearance. It's undeniably one of Stiller's best comedic performances, if not the best.
13 Megamind (2010) - 72%
Already having worked in animated, Stiller was no amateur when it came to providing voice work in Megamind. He plays Bernard, the museum specialist that Megamind impersonates at some point in the film. It isn't a prominent character, but it has Stiller's personality, so it ends up being very funny in the children's film about the alien supervillain who becomes good after someone more evil shows up.
12 Greenberg (2010) - 76%
Noah Baumbach's Greenberg is a very funny drama that tells the story of Roger Greenberg, a young man coming to Los Angeles from New York City after he decides to house-sit for his brother. Stiller's role is so good, his performance stands out as one of the best he's done in drama. This one started his very good relationship with Baumbach.
11 Your Friends & Neighbors (1998) - 77%
The film mostly famous for being the first reviewed film on Rotten Tomatoes is not very good at all. Directed by Neil LaBute, Your Friends & Neighbors tells the stories of several couples who get entangled in each other's relationships. Some of them survive and some of them don't. Roger Ebert was vocally in favor of this one, and no one really agreed with him.
10 Empire of the Sun (1987) - 77%
Bet you didn't remember this one, right? Stiller shows up in Spielberg's Empire of the Sun, even if it's just for one scene. Stiller plays Dainty, an American in the barracks that Jim arrives at, where he learns a lot about the prisoners. Stiller's role is sadly too short, but we can't help but observe the great opportunity Spielberg gave him for what's actually his second appearance on the big screen.
9 Madagascar 3: Europe's Most Wanted (2012) - 78%
In the third entry of the Madagascar franchise, Madagascar 3: Europe's Most Wanted, the gang accidentally ends up in Europe where they join the circus, make some more friends, and get chased by a ruthless animal control officer. Noah Baumbach actually participates in the screenplay for Madagascar 3. This is Stiller's last performance as Alex. For now.
8 Brad's Status (2017) - 79%
Brad's Status is a drama with a few touches of comedy, not the other way around. In the film, Stiller plays Brad Sloan, Troy's father who ends up going with him on a college tour, during which Brad analyzes some of the choices he made that put him below the social status of his old friends. The Mike White drama is an underrated feature that not many people saw upon its release.
7 The Royal Tenenbaums (2001) - 81%
The same year he played Zoolander for the first time, Stiller played Chas, the math genius with an insane talent for business, in Wes Anderson's The Royal Tenenbaums, the film about a family reconnecting after the patriarch reunites them and informs them of a non-existent illness. There's no question this is the Anderson film that put the director in Hollywood's spotlight.
6 Tropic Thunder (2008) - 82%
In Tropic Thunder, Stiller did everything, and perhaps he's the main reason why the film's actually so good. He starred in it, but also directed it, produced it and co-wrote it. In the film, he plays Tugg Speedman, the actor who has fallen out of grace after a notoriously bad role, and is now participating in a war film where things may be more real than he and the rest of the cast thought. This is one of Stiller's best performances.
5 While We're Young (2014) - 84%
Again, a film by Baumbach. This time Stiller plays Josh Srebnick in While We're Young, a film about a couple in their 40s who develop a friendship with a much younger couple. Stiller plays the documentary filmmaker whose relationship with his wife is not the best, but their new friends actually allow him to reconnect with her. This is one of Baumbach's best films to date.
4 There's Something About Mary (1998) - 84%
Raunchy, slopstick and disgusting, that's the style of comedy the Farrelly brothers were able to make in the late '90s, and Stiller had a great participation in their most noteworthy film. Stiller plays Ted Stroehmann, a young man whose greatest memory with Mary isn't the best. The day he was supposed to take her to prom, the zipper in his pants malfunctioned and... you get the idea. Now a thirty-something, Ted tries to reconnect, but he's not the only one after Mary. Stiller as a teenager embodies the traumatic after effects of puberty.
3 Meet the Parents (2000) - 84%
In 2000, Gaylord "Greg" Focker decided to visit his girlfriend's parents with her during a weekend. He's a good-natured guy, and his father-in-law is... not so kind. What happens to Focker during those days will make you cringe. Meet the Parents was the film that confirmed Stiller's ability to make something funny out of basically nothing. Can you imagine if this one had been done by Spielberg and had starred Jim Carrey? It would have resulted in a totally different film.
2 Flirting with Disaster (1996) - 88%
Flirting with Disaster is probably one of David O. Russell's best films. It also features Stiller in the early part of his career playing Mel Coplin, the father of a newborn son whose name he can't decide until he meets his biological mother. That's how Mel, his son, his wife and a social worker embark on a hilarious journey. Stiller is perfect in this very underrated film that not many people have had the chance of seeing.
1 The Meyerowitz Stories (New and Selected) (2017) - 92%
And of course, Baumbach appears on this list again. This time it's with Stiller's highest-ranked film in Rotten Tomatoes with a solid score of 92%. The Meyerowitz Stories tells the story of a family reunion taking place in New York City, as they decide to be vocal about conflicts that made them a dysfunctional group that heavily resemble the attitude of their peculiar father.