Honestly, the early 2000s were a weirdly specific time for the "caper" comedy. We had a massive influx of movies trying to capture that slick, Ocean's Eleven energy, but often with a much goofier, slapstick heart. Right in the middle of that surge sat What's the Worst That Can Happen movie, a 2001 flick that, on paper, should have been an absolute juggernaut. It had the star power. It had a bestselling book as its foundation. Yet, if you mention it today, most people give you a blank stare until you describe the plot involving a stolen ring and a very smug Danny DeVito.
It’s a classic setup. Martin Lawrence plays Kevin Caffery, a professional thief who decides to rob the beachfront mansion of a billionaire media mogul named Max Fairbanks, played by DeVito. Things go south immediately. Fairbanks catches him, calls the cops, and then—in a move of pure, petty spite—takes Kevin's lucky ring, claiming it’s his own. The rest of the movie is essentially a spiraling war of egos. It isn't just about the money anymore; it’s about the principle of the theft.
Looking back, the chemistry here is fascinatingly chaotic. You have Martin Lawrence at the peak of his post-Bad Boys and Big Momma's House fame, leaning heavily into his high-energy, frantic persona. Opposite him, DeVito is doing what DeVito does best: playing a grotesque, morally bankrupt elitist who is surprisingly charming in his villainy. It’s a battle of the short-kings of comedy, and it works better than the critics at the time gave it credit for.
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The Source Material vs. The Screen
A lot of people don’t realize that What's the Worst That Can Happen movie is actually based on a novel by Donald E. Westlake. If that name sounds familiar, it should. Westlake was the mastermind behind the John Dortmunder series, which are legendary in the mystery-comedy genre.
The movie takes some pretty significant liberties with Westlake’s "Dortmunder #9" book. In the novel, the tone is a bit more cynical, a bit more "New York gritty." The film shifts the setting to Washington, D.C., and injects a heavy dose of slapstick that wasn't necessarily the primary focus of the prose. This shift is probably why the movie feels so distinctly like a product of its era. It was directed by Sam Weisman, who had previously done George of the Jungle, so the lean towards physical comedy makes total sense.
You've got a supporting cast that is basically a "who's who" of character actors from the turn of the millennium. John Leguizamo plays Kevin's partner, Berger. Bernie Mac shows up as a flamboyant medium/uncle figure. Even William Fichtner is there, playing an eccentric detective with a very specific, almost effeminate flair that feels... well, it’s definitely a choice that hasn’t aged perfectly, but it’s certainly memorable.
Why it Flopped (And Why That's Unfair)
If we’re being real, the movie didn't exactly set the box office on fire. It opened in June 2001, right as the summer blockbuster season was heating up. It made about $38 million against a $60 million budget. That’s a "flop" by Hollywood accounting standards.
Critics were also pretty harsh. They called it loud. They called it repetitive. But they missed the nuance of the petty rivalry. There is something deeply relatable about the "What's the Worst That Can Happen movie" premise. Everyone has had something taken from them—not necessarily by a billionaire, but maybe by a boss or a "friend"—and felt that burning desire to get even, regardless of the cost. The movie takes that relatable feeling and turns it into a high-stakes heist film.
The pacing is breathless. It moves. You don't have time to think about the plot holes because Martin Lawrence is already in another disguise or Danny DeVito is screaming at his trophy wife, played by Glenne Headly. It’s a 90-minute comedy that actually stays 90 minutes. That’s a lost art in the 2020s where every comedy feels the need to be a two-and-a-half-hour epic.
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The Style and Aesthetic of 2001
Rewatching it now provides a massive hit of nostalgia. The tech is hilarious. Palm Pilots. Giant CRT monitors. Cell phones with antennas. The fashion is even better—oversized suits, tinted sunglasses, and those specific "urban chic" outfits that Martin Lawrence rocked so well.
The soundtrack is a time capsule, too. It’s heavy on the R&B and hip-hop of the era, featuring tracks from Snoop Dogg, Ludacris, and Erykah Badu. It gives the film a groove that most modern comedies lack. Modern movies often feel sterile; this movie feels lived-in, even if that life is a bit cartoonish.
The "Ring" as a MacGuffin
In film school terms, the lucky ring is the ultimate MacGuffin. It doesn't actually do anything. It’s not a magic ring. It’s just a piece of jewelry given to Kevin by his girlfriend (played by Carmen Ejogo). But it represents his luck.
When Max Fairbanks steals it, he isn't just taking gold; he’s taking Kevin’s identity as a "successful" thief. This sets up a series of escalating robberies where Kevin keeps breaking into Max’s life—not to steal his millions, but to get that one specific item back. Max, being a sociopath, realizes how much it means to Kevin and keeps it just to be a jerk. It’s a psychological battle disguised as a slapstick comedy.
Key Moments You Probably Forgot
- The Auction Scene: Max is trying to sell off his assets during a bankruptcy hearing, and Kevin manages to infiltrate the event, leading to a ridiculous bidding war.
- The Gay Detective: William Fichtner’s Detective Alex Tardio is a bizarre highlight. He’s obsessed with "fine things" and has a way of sniffing out crime that is both brilliant and totally weird.
- Bernie Mac's Cameo: He plays Uncle Jack. It’s brief, but Bernie Mac had this way of commanding the screen that makes his few minutes some of the funniest in the whole film.
Does it Hold Up Today?
Sorta.
If you’re looking for high-brow humor or a tightly wound thriller, you’re in the wrong place. But if you want a movie that captures the frantic, colorful energy of the early 2000s, What's the Worst That Can Happen movie is a goldmine. It’s a movie that knows exactly what it is. It’s not trying to win an Oscar. It’s trying to make you laugh at Danny DeVito getting tackled.
The power dynamics are interesting to watch in a post-2020 world. Seeing a "little guy" thief go up against a corrupt billionaire feels even more relevant now than it did twenty years ago. Fairbanks is the quintessential "evil CEO" who thinks he can own everything—even things he stole.
The Legacy of the Cast
It’s worth noting where everyone went after this.
Martin Lawrence remained a comedy staple, though he eventually pivoted back to the Bad Boys franchise which saw a massive revival recently.
Danny DeVito became a god to a whole new generation through It's Always Sunny in Philadelphia. You can actually see shades of Frank Reynolds in Max Fairbanks—the same greasiness, the same love for the "scheme."
John Leguizamo evolved into a massive prestige actor and voice-acting legend (shout out to Bruno from Encanto).
The movie didn't launch a franchise, and it didn't change the face of cinema. But it remains a solid "Sunday afternoon" movie. It’s the kind of thing you catch on a streaming service and realize you’ve watched the whole thing without checking your phone once.
Why You Should Give it Another Shot
- The Chemistry: Lawrence and DeVito are a pairing we didn't deserve. Their height difference alone is a comedic engine.
- The Stakes: Unlike modern movies where the world is ending, the stakes here are purely personal. It’s refreshing.
- The Supporting Cast: Seriously, keep an eye out for the smaller roles. The talent depth is insane.
- The Nostalgia: It is a pure, uncut hit of 2001 aesthetic.
The movie explores a simple question: What happens when two people who refuse to lose run into each other? The answer is a chaotic mess of burglaries, fake identities, and a very stressed-out John Leguizamo.
Actionable Steps for the Movie Buff
If you’re planning on revisiting this era of comedy, don't just stop at this film. To truly appreciate the "Caper Comedy" era, you should pair a rewatch of What's the Worst That Can Happen movie with a few other titles to see how the genre evolved.
- Check out the book: Read What's the Worst That Could Happen? by Donald E. Westlake. It gives you a much deeper appreciation for the Dortmunder character and shows how Hollywood adapts (and sometimes breaks) good literature.
- The "Petty Rivalry" Double Feature: Watch this alongside Big Fat Liar (2002). Both movies deal with a younger protagonist trying to get something back from a powerful, older antagonist who stole their "prize." It’s a fascinating comparison of how the same trope is handled for different age groups.
- Track the Director: Sam Weisman has a very specific "vibe." If you like the energy here, go back and watch The Out-of-Towners (1999) or George of the Jungle (1997). You’ll see the same DNA in the physical comedy.
- Look for it on Streaming: As of now, the movie often rotates through platforms like Max or Tubi. It’s rarely a "premium" rental, making it a low-risk, high-reward watch for a movie night.
Don't go in expecting a masterpiece. Go in expecting two of the funniest men in Hollywood history trying to out-petty each other. In a world of gritty reboots and multiverse fatigue, sometimes a movie about a stolen ring is exactly what you need. It’s loud, it’s colorful, and honestly, it’s a lot of fun. Give it a chance to prove that the worst that can happen is actually a pretty good time.