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The film opens as we see Wayne (Steve Zahn) watching a videotape of a 1972 concert featuring Neil Diamond. We find out that he was born during this concert when his mother went into labor while Neil was performing. He explains (into the camera) that he, Darren Silverman (Jason Biggs), and JD McNugent (Jack Black) are huge Neil Diamond fans and in fact, they even have a band called DIAMONDS IN THE ROUGH.
In flashbacks he explains that the 3 of them have been friends since grade school. Silverman, even in grade school was too trusting of girls. We then see them in high school where JD is the school mascot (an eagle), Wayne is 3rd string QB and Darren is a male cheerleader.
The football coach is a Bobby Knight like coach. In a locker room scene, he explains that they should stay away from girls and sportsmanship is the most important part of the game. Meanwhile, during the game he is constantly throwing tantrums.
We also learn that Silverman's one true love left High School and he hasn't seen or heard of her since. The reason she left high school is that her parents joined the circus. Her mother was the bearded lady and her brother was the dog-faced boy.
After the flashback has ended, we see the three playing a sidewalk concert of Neil Diamond songs. A beautiful young women smiles and seems interested in Silverman but when he goes over to talk to her, she says she has a boyfriend (a street mime).
We next see the three of them in a bar and JD and Wayne are telling Silverman that he needs to get a new girlfriend. He says he always has such bad luck and besides, his only true love was Sandy from high school. In walks Amanda Peet (Judith). Wayne goes over and talks to her and before he can even say a word, she says she's not interested and to get lost. He says that it's not for me, it's for my friend (Silverman). She's still not interested. He goes back and tells Silverman that she wants to talk to him. Silverman goes over, starts to talk to her and she says she's still not interested, so he leaves.
As soon as Silverman is gone, an older man who is a magician sits down. He is so obnoxious that she grabs Silverman, pulls him back and tells the magician that Silverman is her boyfriend.
They begin dating and it eventually becomes serious enough that he moves in with her. After six weeks, he suggests that they have sex. She says that she does not believe in sex before marriage but there are other things they can do to pleasure each other. She pushes his head down to her crotch. We next see them in bed and he is hinting that he would like to be pleasured also. She says, of course and tosses him a girlie magazine and hand lotion.
Silverman takes Judith over to the house where JD and Wayne live. It's a pigsty.
After five minutes, she ends up covered with beer and salsa. She and Silverman leave and she tells him that she can NEVER see his friends again and has to give up the band.
His two friends are upset because they realize that she's controlling plus they just miss Silverman. They can't convince him to give up Judith so they try to bribe Judith to give up Silverman. They offer her Wayne's house but she refuses. Finally, they decide the only way to get rid of her is to kidnap her. They sneak into her house and after a tremendous struggle, in which she definitely has the upper hand, they shoot her with a tranquilizer dart. They take her back and put her in Wayne's garage, chained to an old truck engine. At the same time, Silverman's old girlfriend (Sandy) comes back to town. JD and Wayne try to get Silverman and her to date.
Sandy says that she will see Silverman but in five days, she's going to become a nun and wants it to be strictly friendly. The reason she's becoming a nun is that in the circus, she was in a trapeze act and the man she loved after doing the world's most complicated stunt, slipped through her hands and fell to his death.
Silverman agrees to go on the date because he believes that Judith has died. JD and Wayne dug up a body, put it in Judith's car and pushed it off a cliff.
While keeping an eye on his victim, JD talks with Judith and Judith uses her training as a psychologist to reveal to JD that he is a homosexual. She smashes a lamp on his head, gets the keys and makes her escape. After a long chase, she's just about to get to the police station when Wayne shoots her with a dart and they take her back to his garage. JD and Wayne are worried about what to do with her so they go to the local prison to visit their old football coach. He's in prison because he got mad at one of the referees, picked up the yard marker and threw it at the referee and impaled him.
The coach tells them to kill her.
They try but they can't do it and in fact, Wayne and Judith actually begin to seem interested in each other.
Silverman's date with Sandy is a disaster, mostly because JD and Wayne set him up with electrodes that shock him every time he mentions Judith. Things go wrong and he ends up setting himself and the bar on fire.
We see Wayne and Judith talking and he has done something nice for her. He's brought her food from Arby's. In order to feed her (she's still chained up) he has to remove a catchers mask from her face. After one or two bites, they start kissing passionately. Before things go too far, the football coach shows up. He's been let out of prison and wants to stay with Wayne and JD.
When the coach finds out Judith is still alive, he goes to the garage to kill her. When he gets there she is loose and makes her escape. She runs to Silverman's house and finds Silverman and Sandy on the couch getting ready to make love. When Silverman finds out she's alive, he's torn between the two women but Sandy goes back to the convent.
JD and Wayne go to jail, and Silverman and Judith decide to get married. On the day of the wedding, JD and Wayne are broken out of jail by the football coach. He rams the jail with Wayne's truck. They go to the convent and prevent Sandy from taking her vows. They then go to the local coliseum and kidnap Neil Diamond. They explain to him that they hope his music will prevent Silverman and Judith from marrying. He says he's written all these songs of love and now he's going to see if he can make them work.
We see the wedding about to take place. The minister is reciting the vows to Silverman and Judith and just before they say I do, Neil Diamond walks out on a balcony and starts singing and playing his guitar.
At the same time, Sandy starts walking up the aisle wearing some clothes they got from Wayne's hooker sister. Silverman sees her and realizes that he loves her and tells Judith he can't marry her and rushes to Sandy.
Judith asks what will happen to her when suddenly, Wayne walks up. She walks over and hits him, knocking out a tooth. He slugs her back and knocks out one of her teeth. The fighting soon turns into passionate kisses. (Judith has always been interested in strong opinionated men but settled for Silverman because her first boyfriend was killed in a kickboxing fight.) She is now interested in Wayne because he is what she's really looking for in a man.
This leaves JD and in walks the football coach.
The next scene we see the minister saying "I now pronounce you man and wife" and we see Silverman kissing Sandy.
The minister says it again and we see Wayne kissing Judith.
He says it a third time and we see JD kissing (very passionately) the football coach.
The film ends with Neil Diamond and all the others, singing on stage, back at the concert he was kidnapped from.
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