A mockumentary-style exposé on the rivalry between two of the greatest tennis players of all time who battled it out in a 2001 match that lasted seven days.
A "documentary" on the rivalry between an American tennis player, Aaron Williams (played by Andy Samberg), and an English tennis player, Charles Poole (Kit Harrington, of Game of Thrones fame). Focuses largely on the match where their rivalry reached a climax - Wimbledon 2001, 1st round - a match that took seven days...—grantss
Aaron Williams (Andy Samberg) and Charles Poole (Kit Harington) are professional tennis players who face off in what becomes the longest match in history. The mockumentary explores the backgrounds of the two competitors.
Aaron Williams is considered "The Bad Boy of Tennis." He was found on the streets and adopted by Richard Williams, who raised Aaron with his daughters, Venus and Serena Williams. At the 1996 Wimbledon Finals, his serve hits a line judge, who has an immediate heart attack and dies. Williams falters and loses the championship. At the ceremony following the match, Williams pushes Prince Edward, the Duke of Kent (Howie Mandel), and disappears.
Charles Poole is a child prodigy forced into a tennis career by his mother (Mary Steenburgen), who threatens to disown him if he loses. He appears on a local show hosted by Caspian Wint (Michael Sheen) as a 15 year old and is on track to become the youngest professional tennis player in history. He tells Wint that he idolizes Aaron Williams.
Williams resurfaces in Sweden creating a male underwear line which causes groin chafing. When Williams runs out of funds, he descends into pornography and an addiction to PCP. He is arrested, convicted, and is sent to a Swedish prison.
Two weeks before 2001 Wimbledon starts, Poole is asked by a reporter if he is a better player than Williams, he says yes. This comment reaches Williams, who escapes prison and becomes a free man, according to Swedish law.
Williams claims he will be playing in Wimbledon. The All-England Chair Committee, led by the Duke of Kent, refuses to let him play. Edward Pudding (Fred Armisen), also a member of the committee, believes that letting Williams play will spike interest for the tournament, and he suggests that Williams play an Englishman who is likely to beat him, which turns out to be Poole.
The night before the match, Poole receives a call from Queen Elizabeth (June Squibb), who tells him to "win."
On the first day of the match, Poole wins the first set 6-0. Before the second set starts, a thunderstorm suspends play for the rest of the day.
On the second day, a revitalized Williams takes the second and third sets. That night, Poole gets another call from the Queen.
On the third day, neither Williams and Poole are willing to surrender the match. After eight hours of intense tennis, the match is suspended.
On the fourth day, a female streaker (Lyssa Roberts) runs onto the court. Williams tries to subdue her, but ends up having sex with her. After they finish, a male streaker (Chris Romano) runs onto the court, with whom Williams also has sex. The female streaker runs back onto the court, and a threesome takes place until the match is suspended on account of darkness.
Before the fifth day, Williams arranges a press conference to announce he has located his birth father, British singer Engelbert Humperdinck. He claims he will dedicate his performance at Wimbledon to all Englishmen. After darkness again suspends the match, Poole is beaten in an elevator by the Queen.
Before the sixth day, Williams is hit by a truck, which is implied to be driven by Poole. Williams leaves the hospital and elects to play with one arm. In the 196th game, with Poole serving 98-97 and triple match point, David Copperfield magically appears on Poole's shoulders. Copperfield later claims he was supposed to appear on the Statue of Liberty. Poole, visibly distracted, fails to win the match in the sixth day.
Before the seventh day, Poole and Williams meet at a joint press conference. Williams reveals that a sex tape of himself and Poole's ex-girlfriend Lily has been leaked, enraging Poole. Poole attacks Williams and removes his wig, revealing Williams's bald scalp. The two elect to settle their matters on the court. Queen Elizabeth makes an appearance at the match, and the two players challenge each other to fight.
Poole and Williams charge the net and kill each other after simultaneously hitting each other in the head with their rackets. The documentary ends with video flashbacks of Poole and Williams praising each other.
