The Best Man 2005

Childhood friends Olly Pickering and Murray go their separate ways when Olly leaves for university, beginning a tangled ride through ambition, romance, and misdirection. In London, Olly actually meets James, and an awkward moment—Murray vomiting all over James—seals a hostile start between the two men, setting a tone of witty friction that threads through the entire story.

Olly’s talent for writing earns him a breakthrough when he finishes the first two chapters of a novel and earns a hefty offer: a publisher pays him $50,000 to finish it. Yet success proves slippery, as he encounters writer’s block and eventually finds himself short of money. He takes a job in the city as the assistant to Dana, an editor specializing in self-help books for women, hoping the gig will stabilize his life even as it nudges him toward new kinds of storytelling.

Meanwhile, James is preparing for a London wedding and decides Olly should attend his party. Olly arrives late and is humiliated in Trafalgar Square when he’s splattered with pigeon droppings, forcing him to change into a pair of women’s trousers. The party promises to be a turning point, with James asking Olly to be his best man and to craft a funny speech that would win over everyone.

From the moment Olly enters the party, he feels out of place, and misunderstandings cascade. He’s snapped at by Becka for wearing her trousers, and he also encounters Sarah—without realizing she is James’s girlfriend. On the balcony, Olly experiences an immediate, confusing spark with Sarah, while James is convinced that Olly has fallen for Becka. The tension pulls together a small circle, including Harry and Tania, as well as Graham, who discuss the tangled feelings over pints at a pub. Murray, driven by a plan to derail the wedding, makes a covert bid to ensure the nuptials don’t go ahead.

Murray’s schemes extend beyond the party. He phones Sarah on Olly’s behalf to arrange a film date, tries to cast James as a deceitful womanizer, and rolls out a web of misdirection—arranging a pretend wedding list at Selfridges with Olly, calling from Stan’s porn shop, and even showing up at Becka and Sarah’s flat to insinuate that James plans to sell the flat. The rapid-fire tricks escalate the dramatic farce.

Back at Selfridges, Dana catches Olly in a moment with a wedding dress, throwing the day’s plans into question. The next day, Dana fires Olly, and Graham attempts to persuade her to rehire him, though the reconciliation doesn’t materialize. Instead, Olly discovers that Sarah has found red knickers Murray hid to frame James, and she uncovers the phone number of the porn shop on James’s mobile, prompting her to call off the wedding.

A surprise party for Olly is staged by Murray, with everyone but James in attendance. Murray finally confesses that his scheming was all his idea, and Olly writes a letter to [Sarah] on James’s behalf. James pretends to leave for New York, heartbroken, and [Sarah] begins to believe in the emotional ruse. Olly, meanwhile, is left to wonder whether he has done the right thing, while Murray hints at deeper betrayals.

The truth surfaces when Olly attends James’s stag party, where James admits infidelity to Sarah—an admission that complicates everyone’s plans. Olly wants to reveal the truth to [Sarah], but James handcuffs him to a pillar to stop the confession. Once freed, Olly heads to the wedding venue to interrupt the ceremony, a tense chase through time and pressure. Murray flails to buy himself more time, and Becka steps in to help reveal further complications: James has been unfaithful with his secretary, and another unnamed girl becomes part of the mounting drama.

In the end, [Sarah] calls off the wedding. Six months later, Becka and Murray marry, and Olly and Sarah finally come together. Olly returns to writing, channeling the chaos into a bestseller that confirms his voice—and his future—as a recognized writer.