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You ever wake up missing a tooth, sharing a suite with a tiger, and somehow spark a $469M global phenomenon? That’s The Hangover. It wasn’t just a comedy—it was a cultural reset. No A-listers (at the time), no big expectations, just chaos, chemistry, and a story that slapped. We break down the casting near-misses, Vegas madness, and why this film still outpunches most comedies today (even with Mike Tyson in it).

In this episode, we look at The Hangover, comedy, film ratings, Oscars, character analysis, behind the scenes, Vegas, real-life inspiration, comedy awards, movie analysis, casting, character dynamics, wedding, chaos, Mike Tyson, and film review.

By the Numbers

• Release Year: 2009
• Box Office Gross: $469.3 million
• Rotten Tomatoes Score: 79%
• Director: Todd Phillips
• Budget: $35 million

Main Cast

• Bradley Cooper as Phil – A Star Is Born, American Sniper, Silver Linings Playbook, Limitless
• Ed Helms as Stu – The Office, Cedar Rapids, Vacation, Captain Underpants
• Zach Galifianakis as Alan – Due Date, Baskets, Between Two Ferns, Birdman
• Justin Bartha as Doug – National Treasure, Gigli, The New Normal, Holy Rollers
• Ken Jeong as Mr. Chow – Community, Crazy Rich Asians, Knocked Up, Role Models

Supporting Cast

• Heather Graham as Jade (the stripper Stu marries)
• Jeffrey Tambor as Sid Garner (Alan’s dad)
• Mike Tyson as himself
• Sasha Barrese as Tracy Billings (Doug’s fiancée)
• Rachael Harris as Melissa (Stu’s controlling girlfriend)
• Rob Riggle as Officer Franklin
• Cleo King as Officer Garden
• Bryan Callen as Eddie Palermo (wedding chapel owner)
• Matt Walsh as Dr. Valsh
• Gillian Vigman as Stephanie Wenneck (Phil’s wife)

Fun Facts

• The “Hangover Suite” is real—and it’s at Caesars Palace.
• Mike Tyson filmed his scenes in just one day.
• Jack Black turned down a role in the film.
• The baby in the movie is played by twins (classic Hollywood move).
• Most of the film was shot in actual Las Vegas locations.
• Bradley Cooper’s role helped catapult him into stardom.
• The film inspired actual “Hangover” Vegas party tours.
• Ed Helms’ missing tooth? That’s real—he removed a dental implant.

Movie Mistakes

• Stu’s tooth gap changes sizes in some shots.
• The valet hands over a different car than they arrived in.
• Inconsistent timelines in photos vs. the actual events.
• The cop’s stun gun switches hands mid-shot.
• One scene shows a tiger blinking—tigers don’t usually cooperate so well.
• The chicken randomly disappears without explanation.
• Doug’s mattress isn’t visible from the rooftop during some scenes.

Key Takeaways

• Cunning card counting is a foolproof system, but it’s frowned upon.
• The Hangover is considered one of the best comedies by the hosts.
• Rotten Tomatoes scores don’t always reflect comedy brilliance.
• Comedies deserve real recognition during awards season.
• The Oscars should have separate categories for musicals and comedies.
• Jack Black was initially approached for a role and declined.
• Ed Helms filmed while still doing The Office—not easy.
• The Hangover Suite at Caesars is an actual room you can book.
• Every cast member was a second (or third) choice originally.
• The mystery structure adds clever pacing to the chaotic plot.
• Mike Tyson’s cameo brought an unexpected knockout moment.
• The film still captures the chaos—and charm—of Vegas nights gone wild.