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Brian Stimpson (Cleese), headmaster of Thomas Tompion Comprehensive School, has been elected to chair the annual Headmasters' Conference. Extremely disorganised as a young man, Stimpson is now obsessively organised and punctual, and his school runs "like clockwork". He is the first headmaster of a comprehensive school to chair the Headmasters' Conference, that honour usually being reserved for heads of the more elite private schools.

Despite repetitive rehearsal of his speech and preparations for the journey to the conference, Stimpson's ordered world unwinds as a series of misadventures plague him en route. He misses the train to Norwich, loses the text of his speech, and is left at the train station by his wife, who thinks he departed on the train. Frantic to get to Norwich on time, Stimpson searches for his wife at home and at the hospital where she volunteers, but just misses her. Commandeering the car of a sixth form student, Stimpson travels to the conference with the student, called Laura. Stimpson's wife sees him with Laura at a petrol station and assumes the worst, suspecting that her husband is carrying on with the student and bringing her along to attend the conference. Mrs. Stimpson (who is looking after three senile women) drives after Stimpson and both parties forget to pay for their petrol. The police are called and, responding to a call from Laura's parents (reporting the car as stolen) as well, attempt to find Stimpson and arrest him for kidnapping. Stimpson's wife, Laura's parents, the police and Mr. Jolly, a teacher at Thomas Tompion who has secretly been dating Laura, all pursue Stimpson and Laura to the conference.

En route, Stimpson and Laura try to call the conference from a telephone box. A local mistakes them for vandals when the phones don't work and calls the police. The local sends her daughter to Stimpson, but she turns out to be a childhood friend and former girlfriend of Stimpson. Stimpson coerces her into driving them to the Conference.

The group drive into a farm field and get stuck in deep mud whilst Stimpson's wife and the others arrive at the Conference uninvited, much to the annoyance of the headmasters. Brian leaves the stuck car to seek help, but ends up instead having a bath at a nearby monastery. His ex-girlfriend finally drives away in the car but is soon arrested for assaulting a police officer. Stranded without transport, Laura and Stimpson (who is dressed in monks' robes) attempt to hitchhike. They are picked up by a wealthy car salesman, whom they persuade to come for a walk in the woods. They trick the traveller into swapping clothes with Stimpson under the ruse of naughty fun, but Stimpson and Laura run away and steal his car.

Stimpson finally arrives at the conference in the torn suit of the car salesman and gives an improvised, abrasive speech to the shocked headmasters. During his speech various characters including the old women, Mr. Jolly and Laura's parents walk into the hall. Finally, he directs all of the headmasters to stand and sing the hymn "To Be a Pilgrim", as he often would to his own pupils. He is then accosted by his disappointed wife, Laura's worried parents and several other parties he had hurt over the course of his journey. The film ends as he is led away by several policemen.

• John Cleese as Brian Stimpson
• Penelope Wilton as Pat
• Alison Steadman as Gwenda Stimpson
• Stephen Moore as Mr. Jolly
• Sharon Maiden as Laura Wisely
• Geoffrey Palmer as Headmaster
• Peter Cellier as Headmaster
• Joan Hickson as Mrs. Trellis
• Pat Keen as Mrs Wisely
• Constance Chapman as Mrs. Wheel
• Ann Way as Mrs. Way
• Tony Haygarth as Ivan with the tractor
• Michael Aldridge as Prior
• Sheila Keith as Pat's mother
• Mark Burdis as Glen Scully
• Nadia Sawalha as Mandy Kostakis
• Richard Ridings as Policeman at crash
• Alan Parnaby as Policeman at phone box

The film was an original script by Michael Frayn, then better known as a novelist and playwright. Frayn wrote it on "spec". He said, "I had always wanted to write something about a man who is late because I have considerably problems in relation to that myself, and only get places early by enormous expenditure of psychic energy."

He showed it to theatrical producer Michael Codron, who had produced five Frayn works on stage including the hugely successful Benefactors and Noises Off, and asked if Codron would like to produce it. "I said, 'Why not?'" said the producer. "I've always been interested in movies."

Codron showed the script to Nat Cohen at EMI Films who gave it to the company's head of production Verity Lambert and she agreed to finance. The title was originally Man of the Moment but this was changed when it was realised that had been used for a Norman Wisdom film.

John Cleese was signed to star. "No one will believe it but I didnt have an idea for casting," said Frayn.

Cleese later said the script was "the best I've ever seen. The same day it landed on my front door, I rang my agent and said, 'I have to do this.' "

"Stimpson is a victim of circumstance," Cleese said. "As the pressures increase, his behavior becomes more and more erratic. Comedy is about things always going wrong, and that's just what happens to him. When you first see him, he's in charge. But as events take over and he can't cope-that's when he falls apart."

Codron, Cleese and Lambert had a meeting to decide the director. They selected Chris Morahan, who had directed Frayn's Chekov adaptation Wild Honey on stage and had recently directed Jewel in the Crown for TV.

Filming took eight weeks in June and July 1985 in Hull, Shropshire and Birmingham.

The film was popular in Britain but only played art houses in the US. This prompted Cleese to make A Fish Called Wanda to be accessible to American audiences, to "get out of the art houses" there.

Cleese later recalled a scene, "there was a scene where I had to make a call from a public phone booth. None of the phones worked and I had to go from booth to booth with increasing fury before I found one that did. In England, that scene got a big laugh because no one here expects the phones to work. But it played to total silence in America, where they all expect to get through on a phone the first time."