While in high school, Donny (played by Adam Sandler) has an illicit affair with his female teacher. They are caught having sex behind the curtains in the school auditorium during a school rally. At her trial, she is given 30 years in prison. She is pregnant. Donny's father is granted custody of the child until Donny turns 18. Donny becomes a hero because of this, gets famous as the boy that lived out every high school boy's fantasy of banging the teacher. They even make a television show out of his story. But after 20 years have gone by, Donny's fame has worn off. He is still recognized as the boy who got his teacher pregnant but he is broke. He owes $43,000 in back taxes and the IRS will put him in jail for three years for tax evasion unless he comes up with the money, fast.
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Donny's son left when he turned 18. Donny hasn't seen him since. Donny learns his son, has changed his name from Han Solo to Todd (played by Adam Samberg). Todd tells everyone his parents died in an explosion, rather than admit the truth about his origins. Donny tries everything he can think of to raise the money he needs to pay teh IRS to avoid going to jail. He asks his old friend Vanilla Ice to help him. But Vanilla Ice can't since he works flipping burgers and doesn't have any money either. He even bets his last $20 on a fat guy running the marathon who is the longest shot in the race with odds against him of 8,000 to 1. After exhausting all other possibilities, Donny talks to a reality TV show producer who agrees to pay him $50,000 if he can get his son to meet with him and they both go to the prison together to see the school teacher who is still incarcerated and the TV crew captures it all on camera.
Donny shows up at the mansion where Todd's boss, Steve (played by Tony Orlando) lives knowing he will find his son there. Todd is planning to marry Jamie (played by Leighton Meester). Father McNally (played by James Caan) is supposed to officiate at the wedding ceremony. Todd is very disturbed that his father suddenly shows up but everyone else seems to like him even though Donny is crude and constantly drinking beer. Todd tells everyone that Donny is his best friend to hide the truth that he is his father. Donny makes up a fantastic fake story about how he saved Todd from death on railroad tracks when Todd was going after a burrito he dropped.
They have a wild bachelors' party. Donny discovers that Jamie is cheating on his son with the boss Steve, but Jamie denies it. Todd goes to the prison to see his mother. Donny tries to talk him out of it, but he can't so he goes also to the prison. During the reunion of the three - father, mother, and son - the TV cameras show up. This enrages Todd who no longer wants to ever see his father again. Todd storms off without signing a release, so Donny cannot get paid by the TV producer. Donny hopes to convince Jamie to help him get back in good with his son and goes to where she is only to find her having sex with her brother. Jamie pays Donny $50,000 to keep quiet. When Donny shows up at the wedding the truth finally comes out.
Best part of story, including ending:
It feels a bit uncomfortable that so much fun is made about molestation, masturbation, an elderly woman having sex with men so much younger than her, affairs, incest, and various other kinds of sexual deviances. It is funny at times but borders on very bad taste.
Best scene in story:
I like the scene where Donny is outside on a window ledge of a hotel on a high floor, sneaking around the corner to spy on Jamie to see what she is doing in the hotel room. We already know Donny is never without a beer from earlier scenes. It is very funny when he stops on the ledge to reach down, pull a beer from his sock, pop the top using the edge of the wall and drinks it, even when he is at risk of falling many stories.
Opinion about the main character:
Donny is stuck in the seventies/eighties time frame and never grew up. His taste in music, his hair-style, the car he drives, his friends (who are all now has-beens that were once-famous during those times), all are from the past. This makes him very immature.