Joe (Daniel Craig) is a has-been actor who seemed to have had great success at one time, but who now just spends his time drinking, doing drugs and sleeping with random women. The only person he has in his life is his personal assistant Ophelia, and even she is getting tired of him.

He receives a call from his mother to say his childhood best friend Boots, whom he has not seen in years, has died. He attends to a disastrous meeting with his agent, who has lost interest in Joe and his career. Joe then meets with an up-and-coming director, during which his excessive drinking causes him to lose the part he had hoped would restore his flagging career. His agent tells him that he is washed up, no one wants to work with him, and quits. This causes Joe to go for a drunken swim and have a flashback of his teenage years and his best friend.

The film flashes back 25 years, to a 16-year-old Joe (Harry Eden) and his best friend Boots. We find out Boots has epilepsy and has recently had an attack in the cinema. Joe’s next-door neighbor, a bored housewife named Evelyn, comes on to him and invites him over that evening, where they are almost caught by her unsuspecting husband.

The next day Joe meets up with a popular but quirky girl his own age from town, Ruth. She invites him back to her house where they find out how much they have in common and arrange to meet the next day. On his way to his date, Evelyn coaxes Joe to stop with her and they end up sleeping together. Joe arrives late to meet Ruth, who has been kept company by Boots. Ruth sees love bites from Evelyn all over his neck and storms off. In his frustration, Joe has a fight with Boots.

The next day Evelyn comes on to Joe again and they both go to her house. She proceeds to force her little girl Jane, who was watching the tv, out to play so they can have the house to themselves. While Joe and Evelyn are in bed, Jane finds an old sea mine and detonates it, perishing instantly. Joe, who blames himself, runs away and has not been home since.

We flash-forward to the present day, where Joe has managed to not drown in the sea and goes back to England to attend Boots' funeral, for which he is 3 days late and has missed. His mother and Aunt tell him that Boots died of an aneurysm and has left behind his wife, Ruth, four young children and a lot of debt. Joe goes to visit Ruth at the graveyard who tells him how much she loved Boots and what a wonderful person he was, but how she cannot cry even though it is the saddest moment of her life. His sister tells him that Evelyn also died a few years ago. Her marriage had broken up after Jane died and she married a cruel man who beat her to punish herself. When she finally found the courage to leave him, she was struck and killed by a truck (her head was never found, officials said that it was taken by a fox).

Joe goes back home to the grand house he purchased for his family when his career was going well. He listens to the same music he and Ruth listened to the night they met, and decides to write her a cheque to help her out enclosed with a letter which had a special phrase written in it from a song they shared the night they met. When Joe's sister gives it to her, Ruth breaks down crying.

Chastised by all that has occurred, Joe heads back to Los Angeles and is met by his personal assistant with whom he starts talking about his possibilities as an actor in the future.

The film was mainly shot in Cape Town, South Africa and Malibu, California.

Flashbacks of a Fool is director Baillie Walsh's first feature film. Walsh has directed music videos for, among others, Massive Attack, Oasis and INXS.