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The Best Man (2005) Plot Summary & Timeline

The Best Man (2005) movie poster

The Best Man is a 2005 comedy and romance film directed by Stefan Schwartz, running 1 hour 36 minutes. This page retells the whole story in 655 words (about 3 minutes to read) and covers 14 key events in order, 13 characters, where and when it is set and 3 themes. Looking for the cast, ratings and where to stream it? See the movie page for The Best Man.

to read the plot summary
3 min
key events in the timeline
14
characters profiled
13
themes explained
3
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The Best Man (2005) movie poster
Released
Runtime
1h 36m
Director
Stefan Schwartz
Genres
Comedy, Romance
Original language
English
No spoilers

What Is The Best Man About?

The premise of The Best Man in 316 words, with nothing given away. The full story follows below.

In contemporary London, a city that feels both intimate and relentlessly noisy, Olly Pickering is grappling with a sudden creative drought that threatens the future of his writing career. With savings dwindling, he is forced to take up temporary lodging in the flat of his long‑time friend Murray, whose own life is a restless mix of ambition and improvisation. The cramped, slightly chaotic living arrangement becomes a crucible for humor and tension, as the two navigate the uneasy balance between loyalty and personal aspiration.

The friendship between Olly and Murray stretches back to childhood, yet years apart have left subtle frictions that flare up when old acquaintances reappear. Enter James, a college mate now on the brink of marriage, whose brusque introduction to the pair sets the stage for a series of awkward, yet oddly endearing, confrontations. Their interactions are laced with sharp British wit, the kind that thrives on miscommunication and the occasional uncomfortable silence, establishing a tone that is both comedic and surprisingly tender.

When James asks Olly to stand as best man, the invitation drags him into a wedding orbit he never anticipated. At a pre‑wedding gathering, Olly encounters Sarah, a striking woman he initially mistakes for a peripheral guest. The instant, unspoken chemistry between them hints at deeper connections, while the surrounding cast—Murray’s scheming energy, James’s nervous optimism, and Olly’s own self‑doubt—adds layers of playful uncertainty. Meanwhile, Olly’s stint as an assistant to Dana, a self‑help editor, offers a glimpse into a world of polished professionalism that clashes with his own disheveled creative process.

The film thrives on the restless pulse of a metropolis where personal crises are amplified by the city’s kinetic rhythm. It blends witty banter, awkward social rituals, and the fragile hope of rekindling artistic spark, all while allowing the characters to stumble, argue, and perhaps discover something unexpected about love, friendship, and the stories they’re destined to write.

Full plot

What Happens in The Best Man?

The complete story of The Best Man, from the first scene to the last, in 655 words (about 3 minutes). Spoilers throughout. Names in the text link to 8 cast member pages.

Spoilers ahead

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.

Timeline

The Best Man Timeline: Every Key Event in Order

14 key events in the order they happen, from “Olly's windfall from early writing” to “Six months later: Becca, Murray, and a new life for Olly and Sarah”. 14 events name a place, across 10 locations.

  1. 1

    Olly's windfall from early writing

    Olly completes the first two chapters of a novel and an editor pays him $50,000 to finish it. Writer's block soon hits, and he loses all the money, leaving him broke. The setback forces him to rethink his career and seek steady work.

    When:Early in his career Where:Home

  2. 2

    Olly moves to London to work for Dana

    He moves to London and takes a job as assistant to Dana, an editor of self-help books for women. This new position puts him in the city’s publishing orbit and closer to the social circle he will later encounter. The money trouble from before drives him to accept steady work rather than ideal acclaim.

    When:Shortly after the windfall Where:London

  3. 3

    James's London wedding and party invitation

    James is planning a wedding in London and throws a party to celebrate. He invites Olly to be part of the festivities and to act as his best man. Olly attends, not realizing how tangled his feelings will become.

    When:Before the wedding Where:London

  4. 4

    Pigeon droppings in Trafalgar Square and change of clothes

    On the way to the party, Olly is stuck in Trafalgar Square and is covered in pigeon droppings. Embarrassed, he improvises and changes into a pair of women's trousers. The mishap sets a comic yet chaotic tone for the evening.

    When:During travel to party Where:Trafalgar Square, London

  5. 5

    Love at the balcony: Olly meets Sarah

    On the balcony at the party, Olly finds himself falling for Sarah. James, however, suspects Olly is attracted to Becka instead. The moment sparks a confusing love triangle that drives the rest of the plot.

    When:During the party Where:James's party, London

  6. 6

    Pub debate about the situation and Murray's plan

    In a pub discussion, Harry, Tania, and barrister Graham talk through the situation. Murray reveals that he intends to see the wedding canceled. The mood is tense as alliances shift and plans intensify.

    When:Shortly after the party Where:London pub

  7. 7

    Murray's manipulation of Sarah and Olly's social life

    Murray phones Sarah on Olly's behalf to set up a film date and sow doubt about the wedding. He also stages meetings for Olly with Sarah at Selfridges to shape the wedding list. From Stan’s porn shop, he even phones James, hinting that he should sell the flat.

    When:Between the party and the wedding Where:Selfridges; Stan's porn shop, London

  8. 8

    Dana's wedding dress moment and Olly's firing

    Back at Selfridges, Olly watches Dana try on a wedding dress, despite her supposed marriage and a meeting. The sight unsettles Olly and soon afterward Dana fires him. Graham tries to persuade Dana to hire him back, and instead ends up with a date.

    When:The day after the party Where:Selfridges, London

  9. 9

    Sarah discovers red knickers and James's frame

    Sarah discovers red knickers Murray had hidden to frame James and also finds a porn shop number on James's phone. The evidence convinces Sarah that James has been unfaithful. She immediately calls off the wedding.

    When:After Dana's firing Where:Sarah's home

  10. 10

    Murray's surprise party for Olly

    Murray throws a surprise party for Olly, inviting everyone except James. He finally admits to having plotted everything, and Olly writes a letter to Sarah on James's behalf. James pretends he is leaving for New York, a ruse that deepens the rift.

    When:Sometime soon after Where:London

Show the other 4 events of The Best Man
  1. 11

    James's alleged infidelity surfaces

    Murray tells Olly that James has slept with someone else while dating Sarah. Olly chooses not to believe him, clinging to a fragile loyalty. The rumor further complicates the wedding plans.

    When:Following the party Where:London

  2. 12

    Stag party confrontation

    Olly attends James's stag party, which turns wild with two stripper policewomen. James admits he has been unfaithful and reveals he wants to marry for money and status. Olly contemplates exposing the truth but is restrained when James handcuffs him to a pillar.

    When:Night before wedding Where:James's stag party

  3. 13

    Final intervention at the wedding venue

    Olly reaches the wedding venue and with Becka's help counters James's deception. Becka exposes James's infidelity with his secretary. Sarah decides to call off the wedding.

    When:Wedding day Where:Wedding venue

  4. 14

    Six months later: Becca, Murray, and a new life for Olly and Sarah

    Six months later, Becka and Murray marry. Olly and Sarah end up together, and Olly returns to writing, producing a bestseller. The success seals the new chapter of their lives.

    When:Six months later Where:London

Characters

Who Are the Main Characters in The Best Man?

13 characters, among them Olly Pickering (Stuart Townsend), Murray (Seth Green) and James (Tom Ellis): who each one is and the part they play in the story. Every profile links to the actor’s page.

  • Stuart Townsend as Olly Pickering (Stuart Townsend) in The Best Man

    Olly Pickering (Stuart Townsend)

    Played by Stuart Townsend

    A childhood friend who tries his luck as a writer and ends up navigating love and social awkwardness. He experiences writer's block after a cash windfall and becomes Olly's assistant to Dana's self-help publishing world, ultimately entangled in James and Sarah's wedding drama while seeking to prove himself in love.

    • 💘 Romantic
    • 😅 Awkward
    • 🧠 Ambitious
  • Seth Green as Murray (Seth Green) in The Best Man

    Murray (Seth Green)

    Played by Seth Green

    Olly's friend who plays puppet-master, scheming to derail the wedding. He uses manipulation and schemes to influence Sarah and undermine James, masking his actions with a veneer of mischief.

    • 🕵️‍♂️ Cunning
    • 😈 Manipulative
    • 🎭 Entertaining
  • Tom Ellis as James (Tom Ellis) in The Best Man

    James (Tom Ellis)

    Played by Tom Ellis

    The groom whose outward charm conceals a more calculating desire for status and wealth. He starts the wedding with ambitious plans and becomes entangled in infidelity that threatens the relationship.

    • 💼 Charismatic
    • 😏 Calculating
    • 🗺️ Social climber
  • Anna Chancellor as Dana (Anna Chancellor) in The Best Man

    Dana (Anna Chancellor)

    Played by Anna Chancellor

    An editor who hires Olly and later fires him. She is professional and wary of Olly's personal drama, while pursuing her own romantic connection with Graham.

    • 💼 Professional
    • 🧭 Pragmatic
    • 💬 Witty
  • Amy Smart as Sarah Marie Barker (Amy Smart) in The Best Man

    Sarah Marie Barker (Amy Smart)

    Played by Amy Smart

    James's girlfriend and the wedding's intended bride who unexpectedly falls for Olly. She is decisive and emotionally driven, ultimately canceling the wedding after discovering the truth.

    • 💖 Independent
    • 😌 Love seeker
    • 🎯 Decisive
  • B(

    Becka (Kate Ashfield)

    Played by Kate Ashfield

    Owner of Olly's trousers and a practical voice in the plot. She helps unravel the deception and ultimately solidifies Olly's relationship with Sarah.

    • 🧵 Practical
    • 📣 Direct
    • 🤝 Loyal
  • David Oyelowo as Graham (David Oyelowo) in The Best Man

    Graham (David Oyelowo)

    Played by David Oyelowo

    A barrister who interacts with Dana and provides the moral counterpoint in the group. He navigates the social web of the wedding and dating dynamics.

    • ⚖️ Respectful
    • 🗣️ Persuasive
    • 🧭 Dependable
  • H(

    Harry (Stewart Wright)

    Played by Stewart Wright

    Part of the pub discussions about the wedding, offering commentary on the unfolding drama and the plans to cancel the wedding.

    • 🏷️ Social
    • 🍻 Outspoken
    • 🤔 Observant
  • Jodhi May as Tania (Jodhi May) in The Best Man

    Tania (Jodhi May)

    Played by Jodhi May

    A friend who is part of the social circle and appears in key conversations around the wedding's dynamics and plans.

    • 👗 Fashionable
    • 🗣️ Opinionated
    • 🧭 Loyal
  • S(

    Stan (Martin Hancock)

    Played by Martin Hancock

    Owner of a porn shop who becomes part of the web of mischief and further complicates the plot with unexpected appearances.

    • 🛍️ Quirky
    • 🕳️ Underworld connection
    • 🗺️ Connected
  • Philip Jackson as Mr. Barker (Philip Jackson) in The Best Man

    Mr. Barker (Philip Jackson)

    Played by Philip Jackson

    Family figure associated with the Barker clan, providing social context and expectations around relationships and status.

    • 👔 Traditional
    • 🧭 Authority
    • 🕰️ Respectful
  • V(

    Vicar (Richard Durden)

    Played by Richard Durden

    Religious figure involved in the wedding and its social fabric, adding formal constraint to the romantic chaos.

    • ⛪ Formal
    • 🗣️ Ceremonial
    • 🕊️ Calm
  • B(

    Bride (Akiya Henry)

    Played by Akiya Henry

    Symbol of the wedding ceremony around which the social circle revolves; her role is central to the nuptial event.

    • 👰 Central
    • 💬 Social role
    • 🧩 Key
Setting

Where and When Is The Best Man Set?

The Best Man is set in London, Trafalgar Square and Selfridges. Here is why the place matters to the story.

Where

London, Trafalgar Square, Selfridges

The story unfolds around central London locations. Trafalgar Square provides a chaotic backdrop for Olly's misadventures, while Selfridges serves as a hub for plotting wedding plans and social encounters. The city’s social scene frames the comedy and relational tensions that drive the narrative.

  • 🏙️ London
  • 🗺️ City life
  • 💍 Wedding culture
Themes

What Are the Themes of The Best Man?

3 ideas the story keeps returning to, among them Romance, Deception and Wedding & Social Rituals.

  1. 01

    Romance

    A love triangle emerges as Olly falls for Sarah while James pursues marriage for status. The film examines how attraction can collide with loyalty and social expectations, steering characters toward dramatic choices.

  2. 02

    Deception

    Murray orchestrates a series of lies and misdirections to sabotage the wedding, testing trust among friends and lovers. Characters manipulate perceptions to control outcomes, revealing the fragility of truth in close relationships.

  3. 03

    Wedding & Social Rituals

    The wedding becomes a focal event that exposes hidden motives and social pressures. Parties, stag events, and social gatherings highlight how appearances shape decisions and alter friendships and romance.

Tone & mood

What Kind of Film Is The Best Man?

Light in tone, with fast pacing and a moderate story, going by the plot summary.

Tone
Light
Pacing
Fast
Story
Moderate
Intensity
Medium
Ending
Happy

A fast-paced and witty romantic comedy that follows a chaotic web of misunderstandings and mischievous schemes surrounding a wedding, filled with awkward humor and eventual happy resolutions.

  • witty
  • romantic
  • farce
  • comical
  • mischievous
  • awkward
  • friendship
  • romantic comedy
  • wedding
  • writer's block

Content notes: infidelity.

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FAQ

The Best Man Plot Questions

5 quick answers about The Best Man, taken from the plot summary, character guide and setting on this page and the film’s credits.

What is The Best Man about?

In contemporary London, a city that feels both intimate and relentlessly noisy, Olly Pickering is grappling with a sudden creative drought that threatens the future of his writing career.

Read the full plot summary

When and where does The Best Man take place?

The Best Man is set in London, Trafalgar Square and Selfridges. The story unfolds around central London locations. Trafalgar Square provides a chaotic backdrop for Olly's misadventures, while Selfridges serves as a hub for plotting wedding plans and social encounters.

The setting explained

Who are the main characters in The Best Man?

The story follows Olly Pickering (Stuart Townsend) (played by Stuart Townsend), Murray (Seth Green) (played by Seth Green), James (Tom Ellis) (played by Tom Ellis) and Dana (Anna Chancellor) (played by Anna Chancellor); the character guide covers 13 characters in all.

All the characters

What are the main themes of The Best Man?

The summary picks out 3 themes: Romance, Deception and Wedding & Social Rituals.

The themes explained

Who directed The Best Man?

The Best Man (2005) was directed by Stefan Schwartz and runs 1 hour 36 minutes.

Stefan Schwartz’s films

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