Ben Stiller has built his career in comedic roles over the last thirty years in the film industry and has found great success in multiple iconic roles. Although he's mostly known for his roles in the comedy genre, he has also drifted into more dramatic roles in recent years and is proving that he can also be successful in that realm as well.
Stiller has also written and directed projects he's starred in and hasn't shown any sign that he's slowing down anytime soon as his top-rated film on this list was released just a few years earlier in 2017.
Greenberg (2010) - 76%
Ben Stiller's Greenberg returns to Los Angeles to house sit for his brother and tries to reckon with where his life will lead him as he hasn't found success as a musician in New York.
He meets his brother's assistant (Greta Gerwig) and finds that she is also reassessing her life and they become quick friends, giving them both a happier view on life now that they've found each other.
Madagascar 3: Europe's Most Wanted (2012) - 78%
This third installment in the franchise sees the animated animal group still trying to get back to the New York Central Park Zoo.
They have to travel to Europe to find their penguin and chimp friends and are pursued by an overly determined animal control officer causing them to hide out as circus performers.
Brad's Status (2017) - 79%
This film follows Brad (Ben Stiller) as he wonders how his life has become so different than what he had envisioned in his college years. He reunites with his friends from school and realizes that they all have high paying glamorous jobs and he feels insecure and upset about his own life as he constantly compares himself to those around him.
He wonders who is the most successful of the friend group realizing that it might actually be him after all.
The Royal Tenenbaums (2001) - 80%
This Wes Anderson film follows the Tenenbaum family led by the patriarchal Royal Tenenbaum. The three children, including Ben Stiller as Chas, had a tumultuous childhood with their father, and the brilliance of their youth was lost through familial betrayal and enduring various disasters throughout the years.
Suddenly, the family of characters has to reunite and the differing personalities of the broken family prove difficult to overcome.
Tropic Thunder (2008) - 82%
Ben Stiller co-wrote, directed, and starred in this film about a group of actors shooting a film about the Vietnam War. Immediately their director is killed and the group is stranded, but all of them still believe that they are filming instead of being stuck and in real danger.
They trek through the environment as the prima donna and self-absorbed actors become increasingly uneasy about their situation.
There's Something About Mary (1998) - 83%
This unique rom-com follows a man (Ben Stiller) who never got over his would-be prom date (Cameron Diaz) so he tries to find her in their adult years. He hires a private eye (Matt Dillon) to find her, but things become more complicated when he also falls in love with Mary and finds out that there are multiple men infatuated with her as well.
There's cringy behavior throughout, but in the end, the film has a good message and is hilarious despite its uncomfortable moments.
While We're Young (2014) - 84%
Ben Stiller and Naomi Watts star as a middle-aged couple who appear to be in a rut in their marriage as they realize they aren't as spontaneous as they once were. They meet a free-spirited young couple played by Adam Driver and Amanda Seyfried and are swept up by their energy.
The couples become quick friends as the film navigates a relationship between the four who are separated by generations.
Meet the Parents (2000) - 84%
This iconic comedy follows Greg (Ben Stiller) who is set to meet his soon to be fiancé's parents and immediately begins a tumultuous relationship with her father (Robert De Niro).
It's clear that her father isn't the mild-mannered and sweet person Greg thought he would be and is instead a hardened ex-CIA operative who is not impressed with the man her daughter brought home as he tries to ruin the relationship at every turn.
Flirting With Disaster (1996) - 87%
Ben Stiller stars as Mel Colpin who decides that he has to find his biological parents before he can decide on a name for his own son. The film turns into a farcical road trip as everything goes wrong and Mel and his wife Nancy meet various characters along the way.
Flirting with Disaster balances hilarious moments with more serious themes including family, adoption, and sexuality.
The Meyerowitz Stories (New and Selected) (2017) - 92%
This Netflix comedy-drama film follows a dysfunctional family who reunites to take care of their father and uphold his legacy in the art world as Bard College is set to celebrate his work. The film balances the serious themes of family and funny moments throughout well.
It gives a pretty realistic representation of a dysfunctional family as they have a difficult time reconnecting at first and then goes back and forth on their relationships throughout the movie.