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Top 10 Hilarious Ben Stiller Moments

VO: Rebecca Brayton
Script written by Alex Crilly-Mckean He’s gone full retard, met the parents and gave us Blue Steel. Join as we count down our picks for Ben Stiller’s top 10 most hilarious moments. In this video, we're looking at Ben Stiller's most memorable gut-busting moments in movies and television. From the Zipper (you know which one) to a Latin-American newscaster ready to battle to the death for ratings supremacy, Stiller is not afraid to go where others wouldn't for that one extra laugh. Special thanks to user derfboy00 for submitting the idea on our Suggestions Page at WatchMojo.comsuggest

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Script written by Alex Crilly-Mckean

Top 10 Hilarious Ben Stiller Moments

He’s gone full retard, met the parents and gave us Blue Steel. Welcome to, and today we’re counting down our picks for Ben Stiller’s top 10 most hilarious moments.

#10: Tom Crooze - Mission: Improbable
“MTV Movie Awards” (2000)

For killer action films like “Mission: Impossible II,” it’s understandable that actors may need a stunt double. Well, here’s the most dedicated one yet. In a sketch for the MTV Movie Awards, Stiller played Tom Cruise’s stunt double, who goes the extra mile by impersonating him in every way, to varying degrees of success. Though you have to give him credit, he’s got that laugh down.

#9: Stiller's Key to Success
“Heavy Weights” (1995)

In this Disney flick, Stiller plays fitness fanatic Tony Perkis, who buys out a summer camp where larger children go to lose weight. What follows is a battle of fit vs. fat with Stiller nearly reaching the pinnacle of hammyness. However our choice for his top moment in this film goes to his introduction, where he spouts what is quite possibly the greatest motivational line of all time.

#8: You’re In My World Now, Grandma
“Happy Gilmore” (1996)

In what is quite a sadistic role for an Adam Sandler film, Stiller plays a corrupt and verbally abusive employee of a retirement home, who often attacks Happy’s grandmother. Though he was uncredited for the role, we can’t help but love just how vicious this manager can be.

#7: Ass-Kicking Newscasters
“Anchorman” (2004)

It’s considered one of the funniest films of all time, so of course Stiller would want a piece of it. Playing as a Spanish anchorman ahead of an angry mob of newscasters, Stiller leads the charge in the hopes of taking Will Ferrell’s Ron Burgundy down a peg in a violent clash. Despite the fact that it’s only a brief cameo, we still remember this scene for its sheer zaniness.

#6: Stiller Dances It Out
“Starsky & Hutch” (2004)

Say what you will about the remake, but this scene cracks us up. By-the-book no-nonsense cop David Starsky has little time for fun. That is until he accidentally gets a drop of cocaine in his coffee. The result? Admit it ladies, your ovaries just exploded.

#5: The Toast
“Meet the Fockers” (2004)

Family gatherings are always awkward. Even more so when your father-in-law suspects you of cheating and injects you with a powerful truth serum just to get his point across. This serum however leaves Stiller revealing a little more than you’d like to hear. Probably a family affair best soon forgotten.

#4: Walk Off
“Zoolander” (2001)

Some say this is the role that Stiller will always be remembered for, and we can believe it. A fashion model with a strange pout and stranger accent, he’s the best of the best – that is, before he’s challenged by rival Owen Wilson. They end up facing each other in a walk off, which kind of like a catwalk but it involves the removal of their underwear. How do things turn out? Ouch. Hope David Bowie has some ice on standby.

#3: Food Porn
“Dodgeball: A True Underdog Story” (2004)

Here’s where Stiller returns to the villain-obsessed-with-fitness role, only this time he’s all about the dodgeball. As White Goodman, Stiller plays a slimy, lecherous gym freak whose determination to stay healthy has left him stuck with another unhealthy obsession. And just like that, everyone who watched this movie immediately went off garlic sauce. But don’t worry, he gets his in the end.

#2: Stiller is Simple Jack
“Tropic Thunder” (2008)

It’s the infamous line that got a lot of people angry but had even more laughing their asses off. “Tropic Thunder” is full of Hollywood stereotypes, and Stiller plays the action-hero-who-tries-to-go-serious role. His dramatic character? And Tugg Speedman took his role so seriously; he lived and breathed it. But as his co-star Kirk Lazarus is quick to tell him, his role as Simple Jack may’ve been a bit too much. But that doesn’t stop him from reprising the role one last time.

#1: Stiller's Zipper
“There’s Something About Mary” (1998)

Everyone knows it; every man fears it. It’s the situation that makes every Y-chromosome squeal. In this romantic comedy, we see Stiller talk to a psychiatrist about his old prom date, Mary, and through a flashback, we see how tragedy struck just before their big night together. What follows is probably one of the most cringe-inducing moments in cinema. Gentlemen, you can uncross your legs now.

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