Ben Stiller's Best Movies And How To Watch Them
A man of many characters.
When it comes to some of the funniest movies of the last twenty or so years, I often think of a few actors. People like Robin Williams or Adam Sandler pop up, but one that I’ve always personally loved the most was Ben Stiller. From shows from my childhood to films I’ve only just seen, Ben Stiller has been a big name in movies.
But, where exactly can you watch the best Ben Stiller movies? What streaming platforms have some of his best work? Look no further than right here, because we have a list of his best films (so far) and how you can stream them.
In this hilarious comedy, Zoolander follows Derek Zoolander a model who isn’t the brightest bulb. But soon, he finds himself in a world of trouble, and has to figure his way out of problems he never thought he'd experience.
Zoolander is one of those movies where if you’ve seen it, you never truly forget it. Ben Stiller is stellar in his starring role, making Zoolander, while silly, an entertaining character to root for. Will Ferrell also had a major role in this movie, and honestly, it was one of Ferrell’s best movies, because it makes me want to see him play the villain way more. While there was a sequel, Zoolander 2 is pretty bad, so it's better to just stick to the original.
Stream Zoolander on Paramount Plus.
Rent Zoolander on Amazon.
There’s Something About Mary (1998)
There’s Something About Mary, one of Stiller’s first major starring roles, is a powerhouse comedy about Ted, who's still in love with his high school crush and devastated over an accident that happened years ago that caused them to drift apart. Now, it’s several years later, and he has the chance to possibly reunite with her and fix the mistakes of his past.
Something I’ve always loved about this movie is the chemistry between both Ben Stiller and Cameron Diaz. It’s because of their relationship in this movie that I feel I can call this one of the best romantic comedies out there.
Stream There’s Something About Mary on Starz.
Rent There’s Something About Mary on Amazon.
In this fun DreamWork's animated movie, Megamind tells the story of a supervillain who grows bored of life when he finally defeats his nemesis. Soon, his experiments to create a new hero end up causing more trouble, and now he must become a hero himself to stop the terror.
Ben Stiller voiced Bernard, a small part in the film, who was a museum curator, but his part was important as it played a key role in Megamind trying to win the affections of his true love, and Stiller’s voice-acting talents were great for the role as he had that perfectly academic voice that made Bernard likable.
Stream Megamind on Amazon Prime.
Rent Megamind on Apple TV.
Meet The Parents (2000)
If you’re looking for another hilarious comedy, be sure to check out Meet the Parents. Starring both Ben Stiller and the legendary Robert De Niro, Meet the Parents tells the story of a young man who wishes to propose to his girlfriend, but must meet the parents first, and her dad ends up throwing a wrench in his plans.
Meet the Parents is a great movie. Really, from beginning to end you will be laughing your ass off. Both Stiller and De Niro have such fantastic chemistry that it always makes me wonder why they weren't in more movies together, and they create hysterical moments that will make you snicker.
Rent Meet the Parents on Amazon.
Next up, we have Dodgeball, a hilarious sports comedy. This great movie is about a group of men who team up to try and stop their local gym from getting bought by a huge health company. In order to do that, they enter the ultimate dodgeball tournament.
I could go on for hours about how fun this movie is, and Ben Stiller is just another fantastic part of this cast. White Goodman is such an iconic role for him and seeing him as a villain is always a treat. He's so fun to see angry and upset, but in his own goofy way. Plus, you get to see some sick dodgeball moves. Who thought that dodgeball could be so entertaining?
Reality Bites (1994)
Another one of Stiller’s first major starring roles, Reality Bites is another fun romantic comedy that tells the story of a young woman who is trying to document the life of her friends in her own reality show, called “Reality Bites,” and the struggles that they face on a daily basis.
At first, you wouldn't expect this movie to be as good as it is, but once you get into it, you can tell that it was made by a cast who truly wanted to show a good, funny story. The three leads - Ben Stiller, Ethan Hawke, and Winona Ryder - are all fantastic in their roles and have such wonderful chemistry that I want to see them in more movies together. Stiller shines above the rest as Michael Grates, and gives an excellent portrayal of someone working in television, and shows how an artistic vision can be changed just to fit a certain aesthetic.
Stream Reality Bites on Starz.
Rent Reality Bites on Amazon.
The Secret Life Of Walter Mitty (2013)
The Secret Life of Walter Mitty tells the story of the titular character, a normal man with a seemingly average life, but who has a brilliant imagination that takes him to new places. Through this imagination, his life is changed.
I truly love this film with a passion. I think that Stiller’s acting in this film, particularly, is his best. He shows a full range of emotions; giving us some funny moments, as well as some heartbreaking ones, making this movie enthralling to watch. As someone who grew up with an active imagination, I can understand the need to step into your own made-up world every once and a while.
Stream The Secret Life of Walter Mitty on Amazon Prime.
Rent The Secret Life of Walter Mitty on Apple TV.
Flirting With Disaster (1996)
Another one of Stiller’s first major films is Flirting with Disaster. This fun black comedy tells the story of Mel, who was adopted as a young child and now has a baby of his own. However, he refuses to name his newborn son until finding his biological parents. When Mel gets a lead in the case, it takes him on a wild adventure.
To be honest, I’ve always really loved Flirting with Disaster. I think that out of many of the films here, this is one of Stiller’s most underrated, as it really shows his capability as an actor to not only hold our attention as a lead, but to make us laugh, and the fact that this whole adventure takes them across the United States to so many states is hilarious to me. Someone else I love in this movie is Josh Brolin, who shows great comedic timing in one of his best movies, hands down.
Stream Flirting with Disaster on Pluto TV.
Rent Flirting with Disaster on Amazon.
The Night At The Museum Franchise (2006-2014)
The Night at the Museum franchise is a fun movie trilogy that tells the story of a man who takes a job as a night guard at the Museum of Natural History in New York City. However, things get a bit strange when everything in the museum comes to life once the sun sets.
As a kid, this was one of the first movies I watched with Ben Stiller. His Larry Daley was this silly man who had no idea what to do when the museum started to come to life, but he learned to adapt, and even make friends with the exhibits, which is what made Stiller perfect for this role. He had this NYC attitude which, paired with this script, created an amazing viewing experience for both kids and adults.
One of my favorite pairings that he had was with Robin Williams’ character. Truly one of the best movies to watch if you love Williams. It’s a shame Night at the Museum 4 won’t happen.
Stream the Night at the Museum Franchise on Disney+.
Rent the Night at the Museum Franchise on Amazon.
Tropic Thunder (2008)
Tropic Thunder is a crazy comedy about a director wanting to get as authentic shots as possible while shooting a war film. So, he drops his actors into a jungle in order to capture their true responses. However, as they film, they discover that there's a real war to survive.
Stiller stars as Tugg Speedman, and something about Stiller as this big-time action star running around scared in the jungle has me hollering every time I watch this movie. He is just so hilarious in every scene he's in. While they have recently come out and denounced some of the controversial scenes, such as the use of blackface on Robert Downey Jr., the film still has its hilarious moments that are pure serotonin to my brain.
Stream Tropic Thunder on Paramount Plus.
Rent Tropic Thunder on Amazon.
The Madagascar Franchise (2005-2012)
Let’s look at the Madagascar franchise. This series, following a lion, a zebra, a hippo, and a giraffe from the Central Park Zoo, tells the story of how they ended up on the island of Madagascar because of a plane crash, and now their lives have changed forever.
Ben Stiller voices Alex the Lion, one of the main characters and someone who likes meat quite a lot, and his voice-acting is just perfect. I can’t imagine someone else playing that character, as his voice not only provides that NYC sass but the emotional depth Alex needed. It’s not the best DreamWork's movie - that crown is still owned by The Prince of Egypt - but certainly a fun one, indeed.
Stream Madagascar 2 on Netflix.
Rent Madagascar 2 on Amazon.
Stream Madagascar 3 on Netflix.
Rent Madagascar 3 on Amazon.
Tower Heist (2011)
Last but not least (for movies, at least) we have Tower Heist, a hilarious buddy comedy between Ben Stiller and Eddie Murphy. In this fun movie, two men find out that they have fallen for their employer's Ponzi scheme. So, they decide to steal all his money from his home - in hilarious ways.
So many people forget about this movie, and I don’t know why. It’s so good. There are so many amazing reasons to watch Tower Heist, from Ben Stiller’s as Josh Kovaks, who brings the house down with his hilarious portrayal of the building manager, to Eddie Murphy’s return to greatness with funny jokes. These two need to be in more movies together. Tower Heist is simply not enough. I must see more.
Stream Tower Heist on Starz.
Rent Tower Heist on Amazon.
Honorable Mention: His Friends Episode (Season 3, Episode 22) (1997)
Okay, while this isn’t a movie, I have to mention this. Friends had some amazing guest stars, but Ben Stiller is one of my personal favorites. In this Season 3 episode, Ben Stiller guest-starred as Tommy, a love interest of Rachel’s who really likes to yell. No, that’s not the right word - scream.
And, my God, it’s so funny. There’s something so hilarious about seeing Ben Stiller angry. He just seems like a carefree kind of guy, so to see him get so upset and scream at things makes my side hurt every time I watch it.
Stream his Friends episode on HBO Max.
With all these great films, one can only wonder what Ben Stiller might be doing next. Maybe popping up in some new 2022 movies? That would be a dream.
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Big nerd and lover of Game of Thrones/A Song of Ice and Fire. Will forever hate season eight. Superhero and horror geek. And please don't debate me on The Last of Us 2, it was amazing!