Finding a movie that feels like a caffeinated trip back to the 1930s is rare. Honestly, Peter Bogdanovich’s 2014 film She’s Funny That Way is exactly that. It's a dizzying, door-slamming farce that relies almost entirely on the manic energy of its ensemble. If you’ve ever looked at the She's Funny That Way cast and wondered how they managed to get Owen Wilson, Jennifer Aniston, and Kathryn Hahn in the same room for a low-budget indie, you aren't alone. It was a labor of love for Bogdanovich, a director who practically lived and breathed the Golden Age of Hollywood.
The film follows Izzy (Imogen Poots), a call girl turned actress who gets a "helping hand" from a Broadway director, Arnold (Owen Wilson). But it's not a simple helping hand. He gives her $30,000 to quit the business and pursue her dreams. This kicks off a chain reaction of coincidences that involve his wife, her ex-lover, a private investigator, and a therapist who is—to put it mildly—a total disaster. It’s messy. It’s loud. It’s very New York.
Who is Who in the She's Funny That Way Cast?
At the center of the storm is Owen Wilson. He plays Arnold Albertson, a man who has a bit of a "savior complex" with the women he hires. Wilson does that "whisper-talking" thing he’s famous for, but here it adds to the character's jittery guilt. He’s trying to be a good guy while being a fundamentally dishonest husband. It’s a tightrope walk.
Then you have Imogen Poots. She plays Isabella "Izzy" Patterson with a thick Brooklyn accent that feels like it belongs in a black-and-white movie. Most people remember her from 28 Weeks Later or Green Room, but here she shows off some serious comedic chops. She’s the heart of the movie, even when she’s caught in the middle of a screaming match in a hotel hallway.
Kathryn Hahn is, as always, a scene-stealer. She plays Delta Simmons, Arnold's wife and a formidable Broadway star. Hahn has this incredible ability to look like she’s about to have a nervous breakdown while simultaneously being the most competent person in the room. When she realizes her husband has been "helping" other women with the same script he used on her, the facial expressions alone are worth the price of admission.
Jennifer Aniston Like You’ve Never Seen Her
We have to talk about Jennifer Aniston. Usually, she's the relatable protagonist. In the She's Funny That Way cast, she plays Jane Claremont, the world’s most judgmental and unprofessional therapist. She is mean. She is bitter. She is absolutely hilarious. She wears a wig that looks slightly "off," which only adds to the character's jagged edges. It was a refreshing change of pace for her, moving away from the rom-com sweetheart trope into something much more cynical.
The Supporting Players and Cameos
The depth of this cast is honestly ridiculous. You’ve got Rhys Ifans playing Seth Gilbert, an actor who is desperately in love with Delta (Hahn) and serves as the perfect foil to Wilson’s Arnold. He brings a greasy, rock-star energy to the theater world.
Then there’s Will Forte. He plays Joshua Fleet, a playwright who falls for Izzy without realizing her history with his girlfriend's father. It sounds complicated because it is. That’s the point of a farce.
- Austin Pendleton plays a judge obsessed with Izzy.
- George Morfogen (a Bogdanovich regular) shows up.
- Cybill Shepherd and Richard Lewis play Izzy’s parents. Seeing Richard Lewis in a role where he’s just a grumpy, protective dad is a treat for anyone who grew up watching Curb Your Enthusiasm.
And let’s not forget the cameos. Quentin Tarantino pops up at the very end as himself. Why? Because Bogdanovich was a legend, and when he calls, people show up.
Why the Casting Matters for This Specific Genre
Screwball comedy is dead. Or at least, it’s on life support. To make it work in the 21st century, you need actors who can handle rapid-fire dialogue without making it sound like they’re reading from a teleprompter. This isn't Judd Apatow-style improvisation. It’s choreographed chaos.
Bogdanovich wrote the script with his ex-wife, Louise Stratten, back in the late 90s. It was originally titled Squirrels to the Nuts. The title comes from a line in Ernst Lubitsch’s Cluny Brown. That’s the level of film nerdery we’re dealing with here. The She's Funny That Way cast had to understand that they weren't making a modern "relatable" comedy; they were making a love letter to 1940s cinema.
The chemistry between Kathryn Hahn and Rhys Ifans is particularly sharp. They have this history that feels lived-in, which makes the eventual blow-up in the hotel much more satisfying. If these roles were played by lesser actors, the whole thing might have felt too "theatrical" or fake. But because the cast commits 100% to the absurdity, it lands.
Production Hurdles and the Bogdanovich Touch
This movie took forever to get made. It sat on a shelf for years as a script. When it finally went into production, it was Bogdanovich’s first narrative feature in over a decade. He was the guy who directed The Last Picture Show and Paper Moon. He was Hollywood royalty, but he was also an outsider by the time the 2010s rolled around.
The cast really rallied around him. Wes Anderson and Noah Baumbach even stepped in as producers to help get the film across the finish line. You can feel that sense of community in the performances. There’s a looseness to Owen Wilson’s performance that suggests he was having a blast, even when the plot was spinning out of control.
One of the most interesting things about the She's Funny That Way cast is how many of them are comedic heavyweights in their own right. Will Forte, Jennifer Aniston, and Kathryn Hahn could all lead their own sitcoms (and most of them have). Putting them in a room together and telling them to play "serious" characters in a ridiculous situation is a classic comedic formula that works.
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Real-World Connections
Interestingly, the movie reflects some of Bogdanovich’s own life. He was known for his complicated relationships and his tendency to "discover" actresses. By casting Imogen Poots as a young woman being "mentored" by an older director, he’s almost poking fun at his own reputation. It takes a certain level of self-awareness to make a movie like this.
Is it Worth a Rewatch?
If you like movies like Bringing Up Baby or What's Up, Doc? (another Bogdanovich classic), then yes. The She's Funny That Way cast delivers exactly what you'd expect from a high-energy ensemble. It’s not a "deep" movie. It’s not trying to change your life or offer a profound commentary on the human condition. It’s just trying to make you laugh at a bunch of people running in and out of hotel rooms.
Sometimes, that’s exactly what you need.
The film received mixed reviews when it came out. Some critics thought it was too dated. Others loved the nostalgia. But looking back at it now, especially after Bogdanovich’s passing in 2022, it feels like a precious relic. It’s a bridge between the old Hollywood style and the new Hollywood talent.
What to Look for Next Time You Watch
Pay attention to the background actors and the quick transitions. The movie moves fast. If you blink, you’ll miss a cameo or a subtle visual gag. The way Jennifer Aniston interacts with her "patients" is a masterclass in aggressive comedy. She’s not just playing a bad therapist; she’s playing a woman who genuinely hates everyone she talks to.
Also, watch the scenes with the private investigator played by George Morfogen. His deadpan delivery is the perfect anchor for the more "loud" performances from Wilson and Poots.
Actionable Takeaways for Movie Lovers
If you're a fan of this ensemble or the director, there are a few things you should do to get the full experience:
- Watch the "Original" Inspiration: Check out Ernst Lubitsch’s Cluny Brown. It’s the film that inspired the "Squirrels to the nuts" line and the general vibe of the movie.
- Compare to Paper Moon: If you want to see Bogdanovich at his peak, watch Paper Moon. It shows his mastery of the "old school" style that he tried to recreate with the She's Funny That Way cast.
- Follow the Cast’s Career Arcs: See how Kathryn Hahn transitioned from "the funny best friend" in movies like this to a lead in WandaVision and Tiny Beautiful Things. Her performance here is a clear indicator of the range she always had.
- Listen to the Director's Commentary: If you can find a physical copy or a digital version with extras, Bogdanovich’s insights into why he cast certain people are gold for film buffs.
Ultimately, She’s Funny That Way stands as a testament to a specific kind of filmmaking. It's about timing, personality, and a bit of luck. The cast carried a heavy load to make this retro experiment work, and for the most part, they nailed it.