Ben Stiller has had a truly impressive comedic career. He has fronted some of the greatest American comedies of all time, while giving life to both the Night At The Museum and Madagascar franchises through his excellent leading roles in both. But he has also been in some seriously bad stuff.
There have been a lot of them, so be prepared not to see Madagascar or Night At The Museum on this list.
BEST: Meet The Parents (7.0)
His name might quite literally be Gaylord, but Meet The Parents actually ended up as quite a well-received comedy, despite Robert De Niro taking on one of his more unexpected roles.
It’s a remake of a film that was only released eight years previously and very nearly had the involvement of Steven Spielberg and Jim Carrey, but the safe hands of Stiller and director Jay Roach ended up making something pretty impressive.
WORST: Fresh Horses (5.0)
One of Stiller’s first film roles ever was a relatively minor character in Fresh Horses. It’s a fair distance away from his most well-known comedic roles, and even further away from his now regular box office successes. As a result, both his performance and the film itself were pretty much panned by critics.
BEST: Tropic Thunder (7.0)
With an interesting main cast of Jack Black, Ben Stiller and Robert Downey Jr and a very unique idea behind it, Tropic Thunder was one of those films that seemed like it would be good on paper, but that it wouldn’t do well at the box office.
Instead, the film met expectations, and was a box office hit and received positive reviews thanks to a brilliant cast and some great writing. This is one of the few films about making films that has actually ended up being regarded highly.
WORST: Black And White (4.9)
Another one of the film roles Ben Stiller took on before his explosion into fame was Black And White.
It boasted a main cast that included Jared Leto and Robert Downey Jr, as well as some very early appearances from Michael B Jordan and Elijah Wood, but it failed to make an impact and received almost universally negative reviews.
BEST: There’s Something About Mary (7.1)
Just one year before Black And White, Ben Stiller’s comedy career began its explosion via There’s Something About Mary. The film saw Stiller played Ted Stroehmann.
He starred alongside Matt Dillon and Cameron Diaz in a film that was a surprise box office smash and has been regarded as one of the funniest comedies ever made.
WORST: Envy (4.8)
While still fresh-faced, Ben Stiller was very well-known by the time Envy came out in 2004.
Jack Black might be an incredibly funny man, but it’s not exactly overwhelmingly likely that a film with him in it is going to be a masterpiece- Envy is proof of that. It bombed at the box office and received some very negative reviews.
BEST: The Secret Life Of Walter Mitty (7.3)
The second adaptation of the 1939 short story ended up being regarded as one of the best films of 2013. It follows Ben Stiller’s titular character as he gets up to a series of adventures while trying to recover a photo.
One of the coolest elements of the film is its use of the classic David Bowie track, ‘Space Oddity’, which plays an important part of the narrative. It's an artistic approach, but thanks to the beauty and brilliance of Bowie, it works perfectly.
WORST: Zoolander 2 (4.7)
Back in 2001, Ben Stiller took on the lead role in Zoolander, a story about a narcissistic model who ends up in the middle of an assassination plot.
The film was relatively well-received, but certainly not good enough to warrant a sequel. Until 2016, apparently, when Stiller returned to the role and gained incredibly negative reviews.
BEST: The Royal Tenenbaums (7.6)
In the same year as Zoolander, Ben Stiller teamed up with Owen Wilson for the billionth time in their careers to appear in the Wes Anderson comedy (which was actually co-written by Wilson), The Royal Tenenbaums.
It’s a little surrealist and ironic, but the film was a critical and box office success that has managed to land itself a place at the top of Ben Stiller’s IMDb list.
WORST: The Marc Pease Experience (4.0)
Sitting at the bottom of his list, however, is the 2009 failure of a comedy The Marc Pease Experience. You’ve never heard of it because almost no one went to see it thanks to a flawed release.
Despite Stiller taking on one of the most central roles and a strange amount of anticipation around it, the film was panned pretty much across the board by all critics.
