What's the Worst That Could Happen? is a 2001 American comedy film directed by Sam Weisman and starring Martin Lawrence and Danny DeVito. Loosely based on the Dortmunder novel of the same name by Donald E. Westlake, the film's supporting cast includes John Leguizamo, Bernie Mac, Larry Miller, Nora Dunn, GQ, and William Fichtner.
Thief Kevin Caffery attempts to rob from the home of rich businessman Max Fairbanks. But Fairbanks catches him and steals Caffery's cherished ring that his girlfriend gave him. Caffery is then bent on revenge and getting his ring back with the help of his partners.
Tropes in What's the Worse That Could Happen? include:
- #1 Dime: The 'lucky ring' Amber gives Kevin. The ring is inherently worthless, but once Max steals it from him, Kevin will go to any length to steal it back, and Max will go to lengths to keep it, even when it ends up costing him a fortune.
- Adapted Out: Everything related to the Dortmunder series (although it was light on continuity to begin with) was removed.
- Agent Peacock: Detective Alex Tardio (played by William Fichtner). Impeccably dressed in bright clothing, with an excellent hairdo, carrying a cane, and walking his well-groomed show dogs, he is, nevertheless, great at his job.
- Bavarian Fire Drill: Several of these by professional thief Kevin Caffrey in his attempt to steal his girlfriend's ring back from media tycoon billionaire Max Fairbanks. The two most notable include Kevin and his partner sneaking into Max's private penthouse suite by posing as an Arabian prince (with a Holiday Inn towel around his head); and in the climax a literal example when Kevin's crew starts a phony fire allowing Kevin, disguised as a firefighter, to run right up to Max and steal the ring.
- Bits of Me Keep Passing Out: When Kevin and Berger are trapped in a Laser Hallway, they are forced to remain motionless in awkward positions till Windham arrives to rescue them. When they are released, various limbs have fallen asleep. They continue to stagger their way through the robbery.
- Blind Mistake: When blinded by mace, Earl fires several shots at Max, thinking that he is Kevin.
- Bound and Gagged: Kevin's crew binds and gags the caterers and the auction staff at the bankruptcy auction so they can take their places.
- Candlelit Bath: Tiffany is taking a candlelit bath when Kevin breaks into the beach house.
- Cigar Chomper: Max Fairbanks continually smokes cigars, playing the big tycoon.
- Corrupt Corporate Executive: Max Fairbanks. Amongst the corporate malfeasance seem in the film are declaring bankruptcy as an expediency to avoid corporate responsibility, and attempting to bribe a senate subcommittee.
- Crime After Crime: Kevin's crime spree is a Roaring Rampage of Revenge against Fairbanks to force him to give back the ring.
- Detrimental Determination: Both protagonist and antagonist suffer this: Fairbanks is too driven to tell Kevin to screw himself (by not giving back the ring) to care about the fact he is losing his fortune and may end up in jail from all the dirt Kevin has exposed about him, and Kevin's relationship with his girlfriend becomes turbulent because he refuses to stop his quest to get back the ring.
- Elevator Going Down: Gloria has a brief flashback to her and Max having sex in an elevator.
- Evil Is Petty: Fairbanks catches Kevin in fraganti while the latter is stealing his house and calls the cops. Kevin overall is okay with that. And then Fairbanks lies that the ring is his property just for the sake of the fun of "stealing something from the thief". This puts Kevin on the warpath. And then Fairbanks absolutely refuses to give the ring back even after Kevin has brought him to near ruin and makes clear there is only one thing that will make him stop, and the only other person that doesn't thinks it's stupid is Fairbanks' insane head of security.
- Fake Static: Gloria pretends to be going through a tunnel and losing Max's signal so she doesn't have to tell him what her reading revealed. (See Tarot Troubles below.)
- Fakin' MacGuffin: At the end of the film, Kevin and Max are on a boat fighting over possession of the 'lucky ring', when they both look at the ring (which is on Kevin's finger) and realise it is not the original ring, and that someone has substituted a fake earlier in the caper. It turns out to have been Kevin's girlfriend Gloria, who just wanted this whole damned feud to stop.
- Food Slap: During the confrontation at the banquet, Max dumps a glass of red wine over Kevin's white jacket.
- General Ripper: Max's head of security is a lunatic, still reminiscing the glory days of working for the government during the Cold War. This lunacy is the reason he remains loyal to Max when literally everybody else on his side has become fed up with the damn ring business by the end of the film.
- Handy Cuffs: The Rock Shore police handcuff Kevin with his hands in front of him. This allows him to unscrew the window handle in the police car and escape.
- Hauled Before A Senate Subcommittee: Max is called before a Senate hearing. Kevin and Berger follow Max to Washington to try and rob Max's apartment. There, Kevin learns that Max intends to secretly bribe the senators, and replaces the bribe money with insulting notes in Max's name. While Max later addresses the Senate Committee, he gets a call from Kevin who tells him that if Max will give him his ring back he will give him back his. Max refuses and proceeds to repeatedly curse at Kevin. To the senators, and other viewers, it appears he is speaking to them, with the result being that the hearing ends very badly for Max.
- High-Class Glass: Berger wears a monocle when posing as a German auctioneer in order to hijack the auction.
- Hollywood Law: Chances are that Kevin's ring would not have been handed to Max immediately but would have been impounded by the police as evidence until all case-related formalities were over with and then given "back" to Max (a process that would probably take weeks if not months). But then we wouldn't have a movie.
- If I Wanted X, I Would Y:Uncle Jack: If I wanted to hear myself talk, I'd leave myself a voicemail message!
- It's All Junk: Kevin Caffery risks life, limb and imprisonment to retrieve the 'lucky ring' his girlfriend Amber had given him: becoming involved in an Escalating War with the tycoon who stole it. At the end of the film, Amber presents him with the ring; having retrieved it herself. Amber then presents Kevin with an ultimatum: he can either keep the ring or her, as his obsession with the ring is driving them apart. Kevin considers this for a few minutes, then throws the ring away (where it gets run over by a truck).
- Jerkass: Corrupt Corporate Executive Max Fairbanks. He cheats on his wife, insults his mistress, belittles his attorney, shamelessly uses his personal assistant, and steals Kevin's ring as an act of sheer petty-mindedness.
- Kick the Dog: Max Fairbanks just cannot stop performing this, anything from being a two-timer (and a shitty husband and lover) up to dropping a Cluster F-Bomb in the middle of a Congressional hearing airing live on C-SPAN (seeming more important to tell Kevin he will not return the ring and he can go Sound-Effect Bleep himself than... well... not looking like he should be arrested for misconduct).
- Laser Hallway: Kevin and Berger get trapped in a laser hallway when Max turns on the security system, not realising anyone is in his home.
- Mister Muffykins: Gloria owns a yappy Brussels Griffon (incorrectly identified as a Yorkie) named Pumpkin, that barks at everyone except her and Detective Tardio.
- The Mistress: Max Fairbanks is two-timing his wife with a mistress and is an asshole to both of them. Strangely enough he still is afraid of this affair being discovered (maybe because he doesn't wants to lose any money in the divorce) so Tiffany (the aforementioned lover) manages to make Max do what she wants a couple of times during the film by threatening to tell Max's wife.
- Mugged for Disguise: Edwina and Windham steal uniforms from the wait staff they leave Bound and Gagged when working the auction.
- Only Sane Man: Walter Greenbaum, Max's attorney. He spends the entirety of the movie attempting to extract Max from holes that he insists on digging for himself. He repeatedly tells Max to give the ring back, as the longer he keeps it, the more money it winds up costing them. When Max refuses and insists on going down the path he is on, Walter quits, gets out of the car and walks away, never to be seen again.
- Password Slot Machine: Berger uses one to crack Max's alarm code when he and Kevin break into Max's townhouse. Later Windham uses a similar device when he has to break in to Max's townhouse to rescue Kevin and Berger.
- Pinocchio Nose: Kevin cannot lie without blinking uncontrollably.
- Please Put Some Clothes On: When Max is holding a burglar at gunpoint, Tiffany gets out of the bath to see what is happening. Max tells her in disbelief to go and put some clothes on.
- Potty Emergency: Berger finds himself desperately needing to pee while trapped motionless in the Laser Hallway.
- Race Lift: John Dortmunder is established in the books' cover art to be Caucasian. Kevin Caffery is played by Martin Lawrence.
- Rhymes on a Dime: Playful Hacker Shelly Nix is a wannabe rapper who insists on constantly speaking in rhyme; much to the annoyance of those around him.
- Spill Stain Sabotage: Max inflicts a deliberate Wardrobe Wound on Kevin by dumping a glass of red wine over his white jacket and shirt at the banquet.
- Tarot Troubles: Every time Gloria does a reading on Max, she draws the Five of Swords, which depicts a king with five daggers in his head.
- Title Drop: When Walter is attempting to explain the implication of the bankruptcy deal, Max sneers "What's the worst that could happen?"
- Unspoken Plan Guarantee: The scheme that Lutetia and Amber cook up in the restroom. While Kevin's elaborate heist to retrieve the ring is going down, Amber manages to slip the ring off Max's finger by posing as a masseuse, and presents it to Kevin at the end of the film.
