On July 29, 2011, Charles is killed in a hovercraft accident and his soul is promptly sent to the high spiritual palace of Saint Peter. It is there that Saint Peter determines that Charles is too good for Hell but not good enough to get into Heaven. Consequently, Charles is sent back to Earth in 1987, to re-join his life during the teenage years in order to help himself, through the younger Chazz, make more moral choice.
Charles moves in with his younger self Chazz and his mother. Chazz, Booch and Eugene have a beach party at Venice Beach. Charles tries to prevent Chazz from having the worst night of his life.
Charles tries to convince Chazz to take his sweet but unpopular and geeky neighbour Jane to the Junior Prom instead of the shallow airhead Yvonne.
Charles accidentally changes history when he convinces Chazz to help his mother's boss Wendy Worth, who then tries to seduce him. St. Peter tells Charles that he must stop them from having an affair.
Using cough and sneeze signals, Chazz helps Booch to cheat in their mid-term history exam. Chazz is caught with an incriminating note and it is going to be placed on his permanent record. Helen grounds him for two months. Charles must convince Booch to step forward and take the wrap.
Charles takes steps to change a camping trip he remembers taking with Eugene and Booch that ended with Eugene accidentally shooting him with Booch's gun.
Chazz tries to find a way to get his own car in order to impress the new girl next door.
Booch, Eugene and Chazz head to Las Vegas in search of excitement.
The boys' crazy Las Vegas adventure screeches to a halt when Chazz's mother hunts them down.
Booch bunks with Chazz after a fight with his father, but when he decides to go home, he learns his father dropped dead right after their quarrel.
Chazz encourages a grieving Booch to have fun, which results in a foolish prank
Jealousy strikes when Debbie catches Chazz with another woman.
When Booch's truck breaks down, the boys find themselves stranded at a cantina in Tijuana.
Booch falls for a gang member named Kyla. Her ex-boyfriend Choke swears vengeance
Chazz and Booch drop out of school to pursue a get-rich-quick scheme.
Booch tries to win over the father of a girl he wants to date.
A baby is left on the doorstep, and Booch is its father.
