Honestly, the 2004 rom-com Along Came Polly shouldn't have worked as well as it did. On paper, it's another "Ben Stiller gets humiliated for 90 minutes" vehicle. But look at that along came polly movie cast for a second. It is absolutely stacked with people who had no business being in a "shart" comedy, yet they all committed like they were filming Shakespeare.
You've got an Oscar winner, a few sitcom legends, and a pre-fame Kevin Hart hiding in the background. It’s a bizarre alchemy.
The Neurotic and the Free Spirit
At the center, we have Ben Stiller as Reuben Feffer. He’s an actuary. Basically, he calculates risk for a living, which is the most "Ben Stiller character" job ever. He’s uptight, allergic to everything, and remarkably prone to bathroom-related disasters.
Then there’s Jennifer Aniston as Polly Prince. This was a big deal at the time because Friends was literally ending its ten-year run. People were obsessed with seeing if "Rachel" could carry a movie. Polly is the total opposite of Reuben—she’s a "chaos agent" with a blind ferret named Rodolfo and a complete inability to commit to a zip code, let alone a man.
Philip Seymour Hoffman Stole the Whole Show
If we’re being real, the main reason anyone still watches clips of this movie on YouTube is Philip Seymour Hoffman. He played Sandy Lyle. Sandy is a former child star who is still dining out on a movie he made in high school called Crocodile Tears.
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The man was a genius. He plays Sandy with this unearned, sweaty confidence that is painful and hilarious to watch.
- The basketball scene? Legendary.
- "Rain dance!"
- "White chocolate!"
He treats a pickup game like the NBA Finals despite having zero athletic ability. It’s a masterclass in physical comedy from an actor who, just a year later, would win an Oscar for Capote. That’s the range we’re talking about here.
The Weirdly Famous Supporting Cast
The depth of this cast is kind of insane. You probably forgot half of these people were even in it.
Alec Baldwin shows up as Stan Indursky, Reuben’s boss. He’s loud, aggressive, and has a very strange habit of talking to Reuben while using the urinal. It’s peak Baldwin—intense but deeply silly.
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Then you have Hank Azaria as Claude. He’s the French scuba instructor who steals Reuben's wife on their honeymoon. Azaria is unrecognizable under a thick tan and a ridiculous accent. He’s basically a human cartoon, and he’s perfect for it.
Debra Messing plays Lisa Kramer, the wife who cheats. It’s a bit of a thankless role because she has to be the "bad guy," but Messing sells the sheer absurdity of leaving your husband for a guy who lives on a boat and smells like sea salt.
Don't Blink or You'll Miss Them
- Bryan Brown: Plays Leland Van Lew, the billionaire daredevil Reuben has to insure.
- Missi Pyle: Roxanne, Polly’s friend who is constantly "on."
- Kevin Hart: He has a tiny role as Vic. This was way before he was selling out stadiums.
- Masi Oka: Before Heroes, he was Wonsuk, one of the tech guys.
- Judah Friedlander: The 30 Rock star pops up as Dustin.
Why the Chemistry Actually Matters
People complain that Reuben and Polly don't make sense as a couple. They're right. They don't. But that’s sort of the point of the movie. The along came polly movie cast works because every actor represents a different level of "uninsurable" risk.
Reuben spends his life trying to avoid the "Sandy Lyles" and "Leland Van Lews" of the world. He wants safety. But by the end, the cast helps him realize that a life without risk (or spicy salsa dancing) isn't much of a life at all.
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A Legacy of "Let's Go!"
Twenty years later, the movie is a staple on streaming services like Netflix for a reason. It’s comfort food. You know exactly what’s going to happen, but you want to see Hoffman fall down one more time. You want to see Stiller’s face when he realizes there’s no toilet paper in Polly’s apartment.
The movie didn't reinvent the wheel, but it gave us one of the most overqualified ensembles in comedy history.
What to Do Next
If you’re planning a rewatch, keep an eye out for the small character beats. Specifically, watch Philip Seymour Hoffman’s face during the community theater rehearsals for Jesus Christ Superstar. His portrayal of a "has-been" is actually a very nuanced look at ego and insecurity, tucked inside a movie about a guy with a sensitive stomach.
Check out some of the early 2000s comedies that shared this same "Stiller-verse" energy:
- Dodgeball: A True Underdog Story (Also featuring a wild supporting cast).
- Starsky & Hutch (Peak Stiller/Wilson era).
- Tropical Thunder (For more high-level actors doing absurd characters).
The real magic of the along came polly movie cast is that they didn't wink at the camera. They played the ridiculousness straight, and that’s why it’s still funny two decades later.