Ranking All Of Ben Stiller's Movies From Best To Worst Was An Experience I'm Not Soon To Forget

You think you know Ben Stiller flicks, but this might prove otherwise.

It's crazy to think about what a wild and varied career some longtime, beloved talent in Hollywood have had.

Ben Stiller is definitely one, and though he may have gotten his start through nepotism, there's no questioning he's also got talent and a unique vision.

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Whether it's in front of the camera or behind it, comedy, drama, or any combination thereof, Stiller has delivered some major performances.

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You don't get nearly 60 film credits to your name without exploring range. Here's how I ranked his films among each other.

59. The Nutt House (1992)

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All he did was throw a pie, but he was there.

58. Black & White (1999)

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Don't love Stiller as a cop, even though his signature bad-guy sleaze doesn't go unnoticed.

57. That's Adequate (1989)

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Getting to see Ben and Jerry Stiller work together is special, as seen in this silly mockumentary flick.

56. Next of Kin (1989)

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Another brief but solid villain showing on Stiller's part.

55. The Independent (2000)

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It's a film for film buffs, so you have to love that to love this.

54. I'm Still Here (2010)

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Ben Stiller appears as himself in a tense moment in a weird movie that was ultimately a huge prank.

53. Locked Down (2021)

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No offense to Ben in his role as Guy, but I just wasn't ready for a COVID heist film.

52. Starsky & Hutch (2004)

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A reboot before the reboot era, Ben Stiller is funny but misses the mark a few times in this buddy cop movie.

51. Heavyweights (1995)

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The premise is not it, but considering how other things would have/did deal with the subject of weight, it could be muuuuch worse.

50. Zero Effect (1998)

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Ben Stiller took more of a buddy comedy approach to this role than a detective one, and it made the movie a little better for it.

49. Highway to Hell (1991)

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Not only are Ben and Jerry Stiller in this flick, but so are Anne Meara (Jerry's wife, Ben's mom) and Amy Stiller (Jerry's daughter, Ben's sister). Gotta love a good family-wide effort.

48. If Lucy Fell (1996)

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Ben Stiller as a new-age artist type is something to behold. 

47. Fresh Horses (1988)

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Ben Stiller in a Molly Ringwald late '80s rom-com? He's not the heartthrob, but instead, the edgy best friend that puts him on a different path. It's definitely got so-bad-it's-good value.

46. Envy (2004)

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This movie is an underrated Ben Stiller banger with a solid cast around him that gives this a well-deserved boost.

45. Zoolander 2 (2016)

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Zoolander 2 coming out was a little surprising and the comedy wasn't always spot-on, but there was some nostalgia value.

44. Little Fockers (2010)

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Did this need a third movie? Maybe not, but it's still so enjoyable.

43. Empire of the Sun (1987)

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Stiller's first time in a Spielberg movie is definitely something to note, and though he was early in his career, he held his own in this film based on the novel by J.G. Ballard.

42. The Marc Pease Experience (2009)

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This isn't one of Stiller's most well-known films, but he did his best in the limited-release flick.

41. The Heartbreak Kid (2007)

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Ben Stiller once again takes on the guy desperately seeking happily ever after, only to jeopardize his chances with the choices he makes. Not his best, not his worst.

40. Duplex (2003)

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One half of a deliciously deceived couple, this is a solid dark comedy from Stiller.

39. Your Friends and Neighbors (1998)

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I hate this look but Ben Stiller is great in another dark role.

38. Night at the Museum: Battle of the Smithsonian (2009)

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Again, this one hits differently for history fans young and old. I really enjoyed this but it definitely didn't have the same draw as the first, though it did have more captivating action.

37. Permanent Midnight (1998)

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Stiller is great for his grainy, snide way in this film, a rare but welcome persona he's taken on in films before and since.

36. The Suburbans (1999)

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Ben Stiller's stint in this film isn't big but it is full of fun jabs at the record industry as it was.

35. Madagascar 3: Europe's Most Wanted (2012)

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Didn't see this one but points for being part of a cute series.

34. Stella (1990)

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It's great to see stars like Stiller recall how happy they were to just be in the midst of other stars early in their career, and the film gets a little boost on this ranking for that fact.

33. Nobody Knows Anything! (2003)

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A quick cameo about peaches that's hilarious if you enjoy the film but forgettable if you don't.

32. Madagascar: Escape 2 Africa (2008)

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With the second film, not only did the comedy find it's groove but the franchise really blew up.

31. Hubie Halloween (2020)

Ben Stiller @BenStiller

Hubie. Happy. Whatever. Where’s MY one year anniversary?? Hal L https://t.co/tR136qFV4Y

03:34 PM - 07 Oct 2021

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Hubie Halloween is a cute older-kid-friendly Halloween film where Stiller plays a grumpy orderly...around Adam Sandler. Sound familiar?

30. Along Came Polly (2004)

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Some of the humor in Along Came Polly is a little much for me, but the Ben Stiller/Jennifer Aniston bond makes up for it, though you can debate how believable a pairing they are.

29. Hot Pursuit (1987)

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Ben Stiller's movie debut was in Hot Pursuit, where he played Chris Honeywell, the guy winning over Dan's (John Cusack) girlfriend after he goofed up a chance at the summer of a lifetime with her.

28. School for Scoundrels (2006)

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Nothing about this movie really hit for me. It wasn't bad, but also not too memorable, which can be said for a lot of mid-'00s rom-coms.

27. The Cable Guy (1996)

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Another Gen X hit, the raw and dark movie from actors known for their comedy definitely hit a nerve and has grown more appreciated over time.

26. Keeping the Faith (2000)

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This dramedy sees Ben Stiller as a rabbi trying to figure out love, faith, and dating when a childhood friend blows back into his life.

25. Tenacious D in the Pick of Destiny (2006)

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Ben Stiller may just be the guitar center guy in this one, but who doesn't love the epic adventure that is this movie?!

24. Meet the Fockers (2004)

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We probably didn't need a part three necessarily, but the Meet the Parents universe is too good to pass up.

23. Night at the Museum: Secret of the Tomb (2014)

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Prior to this list, I didn't know there was a third NATM movie, so I can't praise or fault it.

22. Madagascar (2005)

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Ben Stiller is great as Alex the lion and this film is a solid start for a franchise.

21. Megamind (2010)

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Bernard (Stiller) has a funny little arc in this film that's funny aside from the rest of the action. 

20. Tower Heist (2011)

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Stiller teamed up with Eddie Murphy to bring a lot of laughs to a fast-paced heist flick and it worked.

19. Greenberg (2010)

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Ben Stiller takes on dark comedy again in this one, and it's eerily decent.

18. Don't Think Twice (2016)

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Ben Stiller makes a brief appearance as himself in a film about an improv troupe that tries to move on after one of its members hits it big.

17. The Watch (2012)

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A neighborhood watch coming together to avenge a fallen coworker's death is surprisingly touching and a solid moment from Stiller.

16. Flirting with Disaster (1996)

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A bit of dark comedy with lots of heart, Stiller pulls at your heartstrings in this one.

15. Happy Gilmore (1996)

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You may be surprised to learn Stiller's uncredited in this one (I was) because it's pretty memorable for a small role.

14. While We're Young (2014)

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Ben Stiller is funny opposite Naomi Watts as a couple realizing they aren't as hip as they used to be and looking to catch up with a new, younger pair of friends.

13. Mystery Men (1999)

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Mystery Men is full of hilarious people as D-list superheroes getting into some great shenanigans.

12. Night at the Museum (2006)

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Something about this movie was great, especially if you were a low-key history geek like myself. It really felt vibrant and different from what was out there at the time.

11. Anchorman: The Legend of Ron Burgundy (2004)

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Ben Stiller is funny, albeit a little cringy, in a star-studded cast where he played Arturo Mendes.

10. Dodgeball: A True Underdog Story (2004)

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Okay, I may be a bit biased because this is probably one of my favorite comedies ever. That said, bad guy Ben Stiller is kind of amazing, and this is one of the best examples of that.

9. The Meyerowitz Stories (2017)

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This one pairs Stiller up with Adam Sandler again, this time as somewhat estranged siblings of an eccentric dad played by Dustin Hoffman.

8. The Royal Tenenbaums (2001)

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Chas Tenenbaum's over-the-top protective nature after the death of his wife, especially as it applies to his kids, is endearing, as is the rest of the zany Tenenbaum family.

7. Reality Bites (1994)

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Reality Bites isn't just a good Ben Stiller movie, but also his directorial debut. He plays a good, snarky, uptight exec.

6. The Secret Life of Walter Mitty (2013)

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This film was one of many times in Ben Stiller's career that he proves he's got the range, playing an ordinary man who ends up on an extraordinary journey.

5. Zoolander (2001)

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Who can forget the first time they saw Zoolander? The dumb and pretty stereotype is somewhat behind us, but the beauty of this hilarious film still stands.

4. Tropic Thunder (2008)

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Another acting/directing effort that pushes boundaries, Stiller shines as a flailing action star that is desperately trying to hold on to his 15 minutes.

3. There's Something About Mary (1998)

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Taking a second chance with a teenage crush in this film proved to be a winning formula for Stiller in a truly memorable role.

2. Brad's Status (2017)

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Stiller has really come into playing a dad, and those heartfelt moments mean something, especially to viewers who are in that same stage of life.

1. Meet the Parents (2000)

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For a whole generation, this is Ben Stiller's most memorable and best-known movie, and with good reason. Greg Focker is a hilariously relatable character perpetually dealing with everything going wrong in his attempts to impress his girlfriend's family. His chemistry with Robert DeNiro is everything.

That's me, but now time to hear from you! What's your ranking (or at least your top five)? Dish in the comments!