What's the Worst That Could Happen?

What's the Worst That Could Happen?

Year: 2001

Runtime: 94 min

Language: English

Director: Sam Weisman

Budget: $60M

ComedyCrime

A ruthless entrepreneur, Max Fairbanks, and a charming thief, Kevin Caffrey, find their lives unexpectedly intertwined, leading to a series of comedic misadventures. Their differing personalities and ambitions clash as they navigate a chaotic situation, resulting in a battle of wits and egos where the stakes keep rising with each unexpected turn.

What's the Worst That Could Happen? (2001) – Spoiler-Free Movie Summary & Plot Overview

Get a spoiler-free look at What's the Worst That Could Happen? (2001) with a clear plot overview that covers the setting, main characters, and story premise—without revealing key twists or the ending. Perfect for deciding if this film is your next watch.

In a sun‑drenched coastal enclave where sleek high‑rise condos loom over breezy boardwalks, business deals are whispered over martinis and the line between legitimate ambition and reckless excess blurs with every sunset. The city pulses with a restless energy, its glossy veneer hiding a undercurrent of mischievous opportunism that feels both glamorous and absurd. The tone is a bright, fast‑moving comedy, a whirlwind of witty banter and unexpected twists that keep the audience guessing what will tip over next.

Enter Max Fairbanks, a flamboyant entrepreneur whose confidence is as expansive as his towering portfolio. He lives life on his own terms, indulging in lavish parties and extravagant displays while staying blissfully unaware of the precarious financial cliff that may lie ahead. His charm and bravado mask a deeper vulnerability, setting the stage for a collision of ego and circumstance that will test his swagger in ways he never imagined.

Opposite him is Kevin Caffrey, a smooth‑talking thief whose reputation rests on a razor‑sharp wit and an effortless charisma. He glides through the city’s upscale venues with a mischievous grin, always on the lookout for the next clever score. Beneath his carefree exterior lies a keen sense of timing and a talent for reading people, making him an equal parts opportunist and unlikely romantic.

When these two disparate worlds intersect, the result is a cascade of comedic misadventures that hinge on clashing personalities and competing ambitions. Their interactions become a battle of wits and egos, each trying to outmaneuver the other while navigating an increasingly chaotic situation. The stakes rise with every unexpected turn, turning ordinary encounters into a lively game of one‑upmanship that promises both hilarity and high‑octane tension.

Last Updated: August 10, 2025 at 11:44

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Fast-paced rivalry comedies like What's the Worst That Could Happen?

Energetic stories where two opposing personalities engage in a chaotic game of one-upmanship.If you enjoyed the chaotic battle of wits between Martin Lawrence and Danny DeVito in What's the Worst That Could Happen?, you'll love these movies. This section features similar comedies where charismatic rivals engage in escalating pranks and schemes, all delivered with a fast pace and lighthearted tone.

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These narratives typically begin with a personal slight or conflict that sparks a feud. The story unfolds through a series of escalating retaliations, with each character trying to outsmart the other. The structure is built on comedic set pieces and confrontations, leading to a final showdown where the underdog usually wins through cleverness, often with a happy resolution.

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Movies in this thread share a core dynamic: a charismatic duo in opposition, a fast-paced sequence of comedic confrontations, and a focus on witty banter and clever antics over serious stakes. The unifying elements are the light tone, high humor score, and the enjoyable spectacle of a personal war fought with pranks instead of violence.

Charming criminal caper comedies similar to What's the Worst That Could Happen?

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The narrative follows a charismatic criminal or team as they plan and execute a caper, often targeting an arrogant or unlikable figure. The plot is driven by a cat-and-mouse game with authorities or a rival, but the stakes remain comically low. Unexpected twists and humorous failures add to the chaos, leading to an ending where the protagonist's wit and charm ultimately prevail.

Why These Movies?

These films are grouped by their core premise of treating crime as a source of comedic entertainment. They share a light emotional weight, a fast pace to keep the caper energetic, and a central character who is a clever, if sometimes foolish, rogue. The experience is unified by a mood of mischievous fun rather than criminal tension.

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Characters, Settings & Themes in What's the Worst That Could Happen?

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