Ben Stiller has made some of the best comedies of the last 30 years. There’s Something About Mary, Zoolander, Meet the Parents, Tropic Thunder – the hit rate is impressive. But even the funniest people in Hollywood get it wrong sometimes, and Stiller has had a few Ben Stiller flops along the way. With Focker-in-Law reuniting him with Robert De Niro this November, we have gone back through his filmography to rank the worst Ben Stiller movies, from the merely disappointing to the genuinely baffling.
6. Duplex (2003)
Stiller and Drew Barrymore play a young New York couple who buy their dream Brooklyn home, only to find the upstairs tenant, a sweet-seeming elderly woman, is making their lives a misery. Danny DeVito directs, and the black-comedy premise has potential, but the film runs out of ideas long before the end. It is not terrible, just forgettable, which is a strange thing to say about a film that is essentially a two-hour war with a pensioner.
5. The Heartbreak Kid (2007)
The Farrelly brothers, who made There’s Something About Mary with Stiller, reunited with him for this remake of the 1972 comedy. Stiller plays a man who realises on his honeymoon that he has married the wrong woman (Malin Akerman) and falls for another (Michelle Monaghan). The gross-out moments feel forced, and it is hard to root for a lead this unlikeable. Of all the Ben Stiller comedies with the Farrellys’ name on them, this is the one nobody talks about.
4. The Watch (2012)
On paper, it is a strong line-up: Stiller, Vince Vaughn, Jonah Hill and Richard Ayoade as suburban neighbourhood watch volunteers who stumble on an alien invasion. In practice, the jokes lean heavily on improvised crudeness and the sci-fi plot never really takes off. Ayoade gets the best moments, which tells you a lot.
3. Little Fockers (2010)
Pam (TERI POLO) and Greg Focker (BEN STILLER) in the third installment of the blockbuster series–?Little Fockers?.
Little Fockers took a much-loved comedy series and sent it into autopilot. Paul Weitz took over as director, the jokes are largely recycled from the first two films, and an impressive cast, including Dustin Hoffman, Barbra Streisand, Owen Wilson and Jessica Alba, is left with very little to do. It still made plenty of money, which is presumably why we are getting Focker-in-Law. Fingers crossed it is closer to the original than this.
2. Zoolander 2 (2016)
Fifteen years after the original became a cult classic, Stiller directed and starred in this sequel, with Owen Wilson, Penélope Cruz and Will Ferrell along for the ride. The problem is that it is almost entirely cameos and callbacks, and the satire of the fashion world that made the first film so sharp is barely there. For a sequel to a film fans quote endlessly, very little of it is memorable.
1. Envy (2004)
Our pick for the worst Ben Stiller movie. Barry Levinson directs Stiller and Jack Black as best friends and neighbours whose friendship falls apart when Black’s character gets rich by inventing a spray that makes dog mess vanish. Christopher Walken turns up in a ridiculous wig, which helps a little. Two of the biggest comedy stars of the time, an Oscar-winning director, and a film that is mostly painful to sit through. It sat on the shelf for a long time before release, which is rarely a good sign.
Why do Ben Stiller flops happen?
Looking at the list, a pattern emerges: sequels that rely on what worked before, and high-concept comedies built around a single joke. Stiller is at his best playing an ordinary man caught in escalating humiliation, which is exactly why Meet the Parents works so well. When the film forgets that, things fall apart quickly.
For more Hollywood misfires, see our ranking of the 25 worst decisions in movie history. Or compare Stiller’s lows with the worst Tom Hanks movies and the worst Tom Cruise movie.