Unmissable Ben Stiller Movies

by Helen Earnshaw | 26 July 2015

Ben Stiller is one of the most recognised faces in film and one of the biggest and most successful names when it comes to comedy.

Ben Stiller in While We're Young

Stiller has enjoyed a movie career that has spanned almost thirty years and has seen him work both in front of and behind the camera. His returned to the big screen earlier this year with While We're Young, which is about to be released on DVD and Blu-Ray.

We take a look back over Stiller's illustrious career and pick out some of his movies that you really cannot afford to miss.

- There's Something About Mary (1998)

After making his name in smaller roles and TV with his fellow 'frat-packers' Owen Wilson, Will Ferrell, Jack Black and Vince Vaughn, Ben Stiller landed his first leading role in Farrelly Brothers' comedy There's Something About Mary.

Starring alongside Cameron Diaz and Matt Dillon in the offbeat romantic comedy about a former geek who realises that he's still in love with his high school prom date, Stiller goes from one hilarious scene to another as he attempts to rekindle the relationship. But private investigators, dogs, and suspicious hair gel stand in the way.

There's Something About Mary proved to be another comedic gem from the Farrelly Brothers - who had brought us Dumb and Dumber - as the produced a movie that crude, politically incorrect and hilariously funny. Hard to believe that this movie is almost twenty years old.

There's Something About Mary was one of the biggest sleeper hits of 1998 and finished the year as the highest grossing comedy in the U.S. It was also the movie that helped propel both Cameron Diaz and Ben Stiller to stardom.

The movie is widely regarded as one of the best gross-out romantic comedies of the nineties and the iconic image of Diaz's stuck up hair lives on.

- Meet The Parents (2000)

Working alongside the great Robert De Niro gave Ben Stiller his next big role, as the poor fiancé meeting his judgemental father-in-law for the first time.

De Niro is at his comedy best as Stiller's Greg Focker digs himself a very deep hole, from milking cats to destroying a hand-made wedding altar. But as Focker gets more and more suspicious of his in-law's past, De Niro's Jack Byrnes ups the ante in an attempt to drive his new son away.

Meet The Parents hit the big screen back in 2000 and works because Stiller and De Niro make such a good comedic team; De Niro is the overbearing father, while Stiller is the fiance who cannot see to do anything right. Hilarity and rather awkward circumstances are always around the corner and prove to be comedy movie gold.

There is a clear chemistry between Stiller and De Niro and you can see that the two actors are having a ball with these roles and this script.

Upon release, Meet The Parents was a critical hit and a commercial smash as it grossed in excess of $330 million at the global box office. It ended 2000 as the seventh highest grossing behind the likes of Mission: Impossible II and Gladiator.

- Zoolander (2001)

With Meet The Parents giving audiences a taste of how well Stiller and Owen Wilson could play rivals, Zoolander took it to the next level as the pair played warring male models.

When Derek Zoolander (Stiller) loses his crown to 'so-hot-right-now' Hansel (Wilson), his career takes a nosedive and it's up to the dim-witted model to get his life back. Packed full of celeb-cameos and including a catwalk-off, a tragic petrol fight, and an attempted assassination, Zoolander showcases Stiller's ability to tackle ridiculous comedy with heart.

Zoolander may not have been the biggest hit at the box office when it was released, but it has become a real cult hit over the years. In fact, filming is currently underway on the much demanded and highly anticipated sequel.

Zoolander is a crazy, wacky, and satirical look at the fashion industry and is a movie that really doesn't take itself very seriously. This was only the third feature film by Stiller as a director and came after Reality Bites and The Cable Guy.

Zoolander may not be the most successful Stiller film to hit the big screen but the actor will forever by synonymous with the character of Derek and Blue Steel.

- Tropic Thunder (2008)

Those who are fans of Stiller as a director had to wait years before we saw him at the helm again as Tropic Thunder was his first directorial debut since Zoolander.

Tropic Thunder saw Stiller leave behind the rom coms we had seen him in and tackle an action comedy alongside Robert Downey Jr, Jack Black and a terrific cameo from Tom Cruise.

Tropic Thunder was a parody on Hollywood and filmmaking as a group of actors are unknowingly thrown into a drug war, kidnap situation, and believe they must act their roles to get out alive.

Tropic Thunder is widely regarded as one of the best spoof war movies of all time - it was a movie that did push the boundaries and wasn't afraid to go where others feared to tread.

Much like Zoolander, this was a movie that did not take itself seriously and poked fun at a topic that we do regard as very serious. The actors were clearly having a blast in these over the top and outrageous roles and it is Downey Jr and Cruise that really steal the show - they are also barely recognisable.

While the film did cause some controversy, it went on to gross over $188 million worldwide and top the U.S. box office.

- Greenberg (2010)

Stiller left blockbuster comedy behind in 2010 as he teamed up with filmmaker Noah Baumbach for indie comedy Greenberg, in which he played the title role.

The movie followed Roger Greenberg, a forty-something carpenter tasked with housesitting his successful brother's home. While there he meets his brother's young PA and begins putting his life back together.

Greenberg marked the return of Baumbach to the director's chair for the first time since Margot at the Wedding and was the first collaboration between the filmmaker and Stiller.

Greenberg was a movie that really showed off a different side to Stiller - he showed that he could be a dramatic actor as well as a comedic star. It was great to see him show off his versatility and it would be great to see him tackle more roles like this.

In lesser hands, Greenberg would have become a very unlikeable character but Stiller manages to take the edge off just enough for you to really get behind him. This is a movie that is about lost souls who finally find their way - a theme that I think just about everyone can relate to.

Greenberg was one of the best indie movies to hit the big screen in 2010 and Baumbach and Stiller really did make a terrific team.

- The Secret Life Of Walter Mitty (2013)

Stiller returned to the director's chair for the first time since Tropic Thunder in 2013 for The Secret Life Of Walter Mitty. The movie was based on the short story by James Thurber and saw Stiller take on the title role of Walter Mitty as well as being in the director's chair.

Walter Mitty is a Life magazine employee who must track down a missing photo negative for use on the final print cover. His quest takes him away from his mundane life into one of adventure as his fantasies play out for real and he gains the confidence he need to ask out a co-worker.

The Secret Life Of Walter Mitty was another very different film project for Stiller in a movie that explores life and how we choose to live that life - some very interesting and relatable themes indeed.

While the movie doesn't quite live up to its potential, it is still a very charming and engaging film that takes us on a journey with a character that you cannot help but root for.

Packed with charm and comedy, the movie sees Stiller joined on the cast list by a terrific Kristen Wiig and a great cameo performance from double Oscar winner Sean Penn.

- While We're Young (2015)

Teaming up once again with cult director Noah Baumbach, Stiller plays Josh, a man stuck in a rut professionally and romantically.

When him and his wife Cornelia (Naomi Watts) meet 20-something couple Jamie (Adam Driver) and Darby (Amanda Seyfried), who celebrate the retro lifestyle and encourage them to try hip new activities, their relationship gets a new lease of life and Josh is inspired to finish his documentary.

But the appeal of the young couple soon wears off when Josh realises that they aren't as genuine as he once thought.

Stiller gives a terrific central performance and he and Watts make a great and very funny couple. There is something incredibly real about them, that you cannot help connect with them and understand why they want to recapture their youth.

I think While We're Young is one of Baumbach's best - and possibly most funny movies - as three different generations collide. Not only does Baumbach show the differences between them, but also what they can learn from each other.