The show was based on the second act of episode #457 of This American Life, titled "What I Did For Love" and reported by Robbie Brown, in which a high school student, Justin Laboy, falls in love with an undercover police officer, and is ultimately arrested for selling drugs to the officer in an attempt to impress her.

The title is a satirical reference to the 1987 TV show 21 Jump Street which was about undercover narcotics agents in a high school.

He introduces Justin Laboy, an eighteen-year-old senior honors student attending Park Vista Community High School in Lake Worth, Florida.

Though other students say that Naomi rejected him, Justin insists that she tells him that she'll think about it, and he is overjoyed ("What the Heck I Gotta Do").

The Narrator then reveals that Naomi is a twenty-five-year-old undercover cop trying to learn which students are dealing drugs.

Three cousins argue if they should help Justin and are surprised that he would even ask such a thing due to his being a successful student.

Knowing that she can't properly bust him without the monetary transaction, she shoves it into Justin's hands just as a teacher comes into the room which prevents him from returning the money.

Justin receives three years' probation and has to spend a week in jail while the other students point out that he'll never get into college now.