You remember the early 2000s. It was a time of baggy jeans, questionable hair gel, and the absolute peak of the "mismatched buddy" comedy. But there was one film that didn't just try to be funny—it tried to pit two of the biggest comedic forces on the planet against each other in a petty war over a ring. Honestly, it sounds like a slam dunk on paper. You have Martin Lawrence, coming off the massive success of Big Momma’s House, and Danny DeVito, who basically owns the market on playing lovable, high-strung dirtbags.
So, what went wrong?
What’s the Worst That Could Happen? is the 2001 heist comedy that everyone seemingly forgot about until they saw it scrolling through a streaming library at 2 a.m. It wasn't just a movie; it was a $60 million gamble by MGM that, unfortunately, didn't pay off. But looking back at it now, in 2026, the film is a fascinating time capsule of a specific era of Hollywood ego and slapstick.
The Plot: A Petty War Over a "Lucky" Ring
Basically, the story revolves around Kevin Caffery (Lawrence), a professional thief with a refined palette, and Max Fairbanks (DeVito), a billionaire who is about as ethical as a hungry shark. Kevin tries to rob Max’s beachfront mansion, but he gets caught red-handed.
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Instead of just calling the cops and moving on, Max notices a ring on Kevin's finger—a gift from Kevin's girlfriend, Amber (played by Carmen Ejogo)—and decides to steal it. He tells the police it’s his. This is the catalyst for the entire movie. A billionaire steals from a thief because he can. It’s petty. It’s mean. It’s the perfect setup for a DeVito character.
Kevin spends the rest of the movie trying to get that ring back, escalating the stakes from simple burglary to systematic character assassination. He even ruins Max’s chances during a Senate hearing. It’s a "pissing contest," as some critics called it at the time, that stretches from mansions to bankruptcy auctions.
A Cast That Should Have Been Unstoppable
Look at this lineup. Seriously.
- Martin Lawrence as Kevin Caffery
- Danny DeVito as Max Fairbanks
- John Leguizamo as Berger (Kevin’s sidekick)
- Bernie Mac as Uncle Jack
- William Fichtner as the eccentric Detective Tardio
- Glenne Headly as Gloria
- Larry Miller as the security chief
If you put these names on a poster today, people would lose their minds. Bernie Mac alone brought a level of energy that usually saves any scene he's in. Yet, the film currently sits at a brutal 10% on Rotten Tomatoes.
Why What’s the Worst That Could Happen? Still Matters
Critics panned it. They said the script was uninspired and the gags were "lame." But here’s the thing: it’s actually a decent window into the work of Donald E. Westlake. The movie is loosely based on one of his Dortmunder novels. If you know Westlake, you know he writes about the "working-class thief"—the guy whose plans always go sideways.
The film captures that "everything that can go wrong, will go wrong" vibe, even if it trades Westlake’s dry wit for Lawrence’s trademark physical comedy.
The Box Office Disaster
The numbers weren't pretty. MGM dumped $60 million into the production. On its opening weekend in June 2001, it pulled in about $13 million, ranking fifth. It eventually limped to a domestic total of $32.2 million. By the time it finished its international run, it hadn't even cracked $40 million.
It was a flop. A big one.
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MGM even took a massive write-down on the project. Some reports suggest the combined losses from this and Josie and the Pussycats cost the studio north of $40 million that year. Three weeks after it opened, high-level marketing and distribution executives at MGM were replaced. Hollywood is a tough room.
The "Invisible" Legacy of the Movie
Despite the failure, the movie has some genuinely weird and memorable moments. William Fichtner’s performance as Detective Tardio is bizarre. He’s a detective who walks dogs and has a strange, almost ethereal presence that feels like it belongs in a Coen Brothers movie rather than a standard studio comedy.
And then there's the ring itself. By the end, we find out the ring might actually be "bad luck." Amber (the girlfriend) eventually reveals she's the one who snagged the real ring back, and she tells Kevin to just throw it away. It’s a cynical, funny ending that fits the title perfectly.
Actionable Takeaways for Movie Buffs
If you’re planning a 2000s comedy marathon, don't just skip this because of the Rotten Tomatoes score. Here is how to actually enjoy it:
- Watch for the Side Characters: John Leguizamo and Bernie Mac are the real stars here. Their chemistry with Lawrence provides the few moments of genuine, unforced laughter.
- Appreciate the Practical Effects: This was before every single explosion or car chase was smoothed over with CGI. The physical stakes feel real because, well, they were.
- Context is Everything: Compare this to Big Momma's House or Blue Streak. You can see Lawrence trying to transition into a slightly more "sophisticated" heist lead, even if the script didn't quite get him there.
The film didn't reinvent the wheel. It barely kept the wheel on the axle. But the pairing of Lawrence and DeVito is a specific kind of magic that we don't really get in the era of ensemble superhero casts. It was a battle of the egos, a clash of comedic styles, and a very expensive lesson for MGM.
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To get the most out of your rewatch, look for the deleted scenes available on digital releases. They often contain more of the improvised riffing between Lawrence and Leguizamo that was cut for time, offering a glimpse into the funnier movie that could have been. Turn off your "critic brain," grab some popcorn, and just enjoy the chaos of two legends trying to out-act each other for 95 minutes.