Plot: Dan Landsman is the self-appointed chair of the twenty year reunion committee of his class' graduation from Grant Barklidge High School in Pittsburgh, where he still lives with his wife, the former Stacey Polster, who graduated in the same class. He tries to control everything about the reunion to appear the big, successful man that he was not but so wanted to be in high school. To furthest bolster himself, he, to his former classmates, refers to himself as "cool" nicknames he gave himself, as no one else would or does. His high school experience clouds the way he parents his and Stacey's fourteen year old son, Zach Landsman, who needs some male parental guidance as he contemplates entering the dating and sexual world. Dan's current actions and how he was in high school irks the other committee members, who still shun him behind his back. As the response rate by their classmates to attend the reunion is less than overwhelming, Dan believes he can be the toast of the class if he can convince who was arguably the most popular person in their class, Oliver Lawless, now a Hollywood actor, to attend the reunion, Dan who likes to think that they were friends in high school which is the farthest thing from the truth. Even if Dan can find and meet with Oliver, convincing him may be difficult as he is probably too cool a person to partake in things like high school reunions. Dan's actions to persuade Oliver to attend the reunion turns to a full on obsession with the occurrence of a specific incident. That obsession will affect Dan's job and his relationship with his boss, Bill Shurmur, who is still stuck in the pre-computer age, Dan's relationship with Stacey and Zach, Dan's thoughts about the reunion and his friendships especially with the other committee members, and Dan's own opinions about what he thinks he wants in life.
Alternative Plot: A nebbish (Jack Black) spins a web of lies around a famous former classmate (James Marsden) to win his friendship and persuade him to attend their high-school reunion.
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