Let’s be real. There’s something deeply satisfying about watching two people who absolutely loathe each other get trapped in a legal nightmare together. In 2008, What Happens in Vegas gave us the peak version of this. Cameron Diaz is a high-strung trader, Ashton Kutcher is a slacker, and through a blur of free booze and bad decisions, they end up married with a $3 million jackpot on the line.
A judge—played with incredible snark by Dennis Miller—refuses to grant an annulment and freezes the cash, forcing them to "make it work" for six months. It’s a classic setup. It works because it taps into that "enemies-to-lovers" trope we can't quit.
If you’re hunting for movies like What Happens in Vegas, you aren't just looking for a romantic comedy. You're looking for that specific blend of high-stakes accidental marriage, "get rich quick" schemes gone wrong, and slapstick comedy that makes you feel slightly better about your own life choices.
The Best Accidental Marriage and "Fake Dating" Gems
Most people forget that the "stuck together" trope is the backbone of the best rom-coms. It’s not just about the romance; it’s about the friction.
1. The Proposal (2009)
This is probably the closest spiritual successor you’ll find. Sandra Bullock is a terrifying book editor facing deportation to Canada, so she blackmails her assistant, Ryan Reynolds, into a fake marriage. Like What Happens in Vegas, the comedy comes from the pure, unadulterated spite between the leads. The scene where they have to tell their "origin story" to a skeptical immigration officer is basically the New York version of the courtroom scenes in Vegas.
2. Overboard (1987 or 2018)
The original Goldie Hawn and Kurt Russell version is a masterclass in the "forced together by a lie" dynamic. A wealthy, entitled woman gets amnesia, and a carpenter she previously mistreated convinces her they’re married to get revenge (and a free nanny). It’s ethically questionable, sure, but the chemistry is undeniable. The 2018 gender-swapped remake with Anna Faris and Eugenio Derbez follows the same beat, keeping that "enemies-to-lovers" friction alive.
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3. Honeymoon in Vegas (1992)
If you specifically liked the Vegas setting, this Nicolas Cage classic is mandatory. It’s a bit more "indecent proposal" than "jackpot winner," as Cage’s character loses his girlfriend in a high-stakes poker game to a gambler played by James Caan. It features a skydiving team of Elvis impersonators. Honestly, what else do you need?
Why the "Marriage of Convenience" Trope Never Dies
We see this everywhere. From Green Card (1990), where Andie MacDowell marries Gérard Depardieu for an apartment, to Netflix’s Purple Hearts. Why does it work?
Experts in film theory often point to the "forced proximity" mechanic. When two people are legally or financially obligated to stay in the same room, the masks drop. In What Happens in Vegas, Joy and Jack have to see each other at their absolute worst—brushing teeth, stealing the covers, and actively sabotaging each other's lives.
"The best rom-coms aren't about the first kiss. They're about the 500th argument that finally makes sense." — Every rom-com fan ever.
Movies Like What Happens in Vegas with High Stakes
Sometimes it’s not just about the ring; it’s about the money. Or the job. Or the house.
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How to Lose a Guy in 10 Days (2003)
Kate Hudson and Matthew McConaughey aren't married here, but they are both "using" each other for professional gain. She’s trying to get him to dump her for an article; he’s trying to make her fall in love to win a bet. The "Benny Boo-Boo" scenes and the yellow dress are iconic for a reason. It captures that same petty, competitive energy that Jack and Joy have while trying to win the $3 million.
The Ugly Truth (2009)
Gerard Butler and Katherine Heigl take the "opposites attract" thing to a very cynical level. It’s loud, it’s a bit crude, and it relies heavily on the two leads being gorgeous while acting like total idiots. If you enjoyed the slapstick side of Ashton Kutcher’s performance, Butler’s Mike Chadway hits that same note.
Life as We Know It (2010)
This one swaps the jackpot for a baby. Two people who had a disastrous first date are forced to live together and raise their best friends' child after a tragedy. It’s a bit heavier than a Vegas weekend, but the "we hate each other but have to share a house" vibe is identical.
The Hidden Complexity of the "Vegas" Formula
Let's look at the numbers for a second. What Happens in Vegas wasn't exactly a critical darling—it sits at a 25% on Rotten Tomatoes. But it made over $219 million worldwide.
Why the disconnect?
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Critics often hate these movies because they’re "predictable." But for the rest of us, that’s the point. We want to see the growth. We want to see the "control freak" Joy learn to loosen up and the "slacker" Jack learn to care about something. It’s a comfort watch.
Common misconceptions about these movies:
- They're all the same: Not really. Some focus on the legal battle (like Intolerable Cruelty), while others focus on the culture clash (like Fools Rush In).
- The characters are unlikable: Joy and Jack are supposed to be annoying at first. That’s the "character arc" part of the movie.
- Vegas is always the hero: Actually, most of these movies use Vegas as the "mistake" and New York or LA as the place where the real work happens.
Fresh Recommendations for 2026
If you've seen the classics, try these:
- Anyone But You (2023): Sydney Sweeney and Glen Powell in a "we hate each other but let's pretend to be a couple at a destination wedding" scenario. It’s basically the modern-day blueprint for movies like What Happens in Vegas.
- The Hating Game (2021): Pure workplace rivalry that feels exactly like the petty sabotage Jack and Joy pull on each other.
- Ticket to Paradise (2022): George Clooney and Julia Roberts as a divorced couple who team up (angrily) to stop their daughter from getting married. The bickering is top-tier.
Actionable Steps for Your Next Movie Night
If you're ready to dive into a marathon, don't just pick at random. Categorize your mood first.
- For the "Vegas" Vibe: Watch Fools Rush In (Matthew Perry and Salma Hayek). It’s the "one-night stand leads to marriage and a baby" story, and it's surprisingly sweet.
- For the "Legal Battle" Vibe: Go with Intolerable Cruelty. Catherine Zeta-Jones and George Clooney as a gold-digger and a divorce lawyer. It’s directed by the Coen brothers, so it’s much sharper than your average rom-com.
- For the "Pure Chaos" Vibe: Re-watch The Hangover. It’s not a romance, but it captures the "what did we do last night?" panic better than anything else.
To get the most out of these, look for the supporting cast. In What Happens in Vegas, Rob Corddry and Lake Bell almost steal the show as the cynical best friends. A good rom-com is only as strong as the people rolling their eyes in the background.
Start with The Proposal if you want the exact same energy, or Anyone But You if you want something that feels a bit more current.