Plot
Tim Conrad (Paul Rudd) is a mid-level financial executive, who acquires a negotiation over special novelty lamps with wealthy Swiss businessman Martin Mueller (David Walliams). Impressed by Tim's ingenuity, his boss Lance Fender (Bruce Greenwood) invites him to a "dinner for winners" in which he must find and bring an eccentric person with a special talent; the winner earns a trophy and the executive that brought him or her gets glory. He soon learns it is more of a "dinner for idiots," and the partygoers will be mocked mercilessly. Meanwhile, Tim's girlfriend Julie (Stephanie Szostak) lands a curator deal for eccentric artist Kieran Vollard (Jemaine Clement), and Tim unsuccessfully proposes to her, as he has done several times before. After learning of the cruel nature of the dinner party, Julie becomes upset and asks him not to attend and he agrees.
The next day, Tim accidentally hits IRS employee Barry Speck (Steve Carell) with his car when Barry tries to retrieve a dead mouse in the road. Witnessing Barry's bizarre behavior (he taxidermies mice and arranges them into elaborate dioramas), Tim realizes he is the perfect loser for the dinner. That night, Barry shows up at Tim's apartment unannounced and accidentally invites over Darla (Lucy Punch), who had a one-night stand with Tim years ago and has been stalking him. Barry decides to guard Tim's apartment from Darla to make up for inviting her. When Julie arrives at his apartment, Barry mistakes her for Darla and sends her away, giving Julie the mistaken impression that Tim is cheating on her. Barry decides to call Vollard and finds the number saved in the phone. While talking to him, he and Tim think they hear Julie in the background and head to Vollard's apartment. Barry tosses Tim's keys through Vollard's apartment window and must break in, only to find out she isn't there and head back home.
Afterward, Barry opens the door to find Darla waiting outside. Julie calls and asks Tim if he's having an affair and Darla steals the phone and stuffs it down her pants. While Tim hides in his bedroom, Darla and Barry get into a bar-styled fight, scaring Darla away. Julie accidentally left her phone at Tim's apartment and a voice message from Vollard reveals to Tim and Barry that Julie is leaving for his ranch. Barry works for the IRS and offers to take Tim to work to find Vollard's ranch address, where they meet up with Barry's boss and rival, Therman Murch (Zach Galifianakis) (who stole Barry's wife), who displays his "mind control" power over Barry. Tim leaves the next day for his brunch with the Muellers but Barry crashes, with Darla pretending to be Julie, when he gets a call from Tim's assistant telling him to bring a still missing Julie. Tim is pushed into asking Darla to marry him by Barry and Julie walks in during. Tim and Barry chase Julie down to Vollard's ranch, where Tim accidentally offends Barry (which further hurts his and Julie's relationship).
To Tim's surprise, he finds Barry already at Fender's dinner party. Barry is a hit with the group and is a shoo-in for the trophy, but unexpectedly, Barry's boss arrives. Tim then tells Barry everything and, after some encouragement, gets Barry to win, before causing his boss and fellow executives to reveal the truth. A guest reacts badly to the news and inadvertently causes chaos in the process, with Mueller losing a finger. A fire breaks out, while a bird brought by one of the guests flies away with Mueller's finger. Tim is fired, as is Julie after Barry makes Vollard realize it would be a problem to have her continue working for him. In the end, Tim marries Julie, Barry enters into a relationship with Darla, does some artwork with Vollard, and hosts a monthly "breakfast for champions" for all of the losers. Therman writes a new book in the mental hospital and Tim gets a new museum started in Switzerland for Mueller. After the closing credits, it is revealed Fender's company has gone under and Forbes Magazine has named him "Wall Street's Biggest Loser."
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