21 Chump Street is a fifteen-minute musical written by composer Lin-Manuel Miranda, who most notably created the Broadway musicals In the Heights and Hamilton. The show was based on an episode of This American Life, where a high school student fell in love with an undercover police officer, and ultimately was arrested for selling drugs to the officer in an attempt to impress her. The musical premiered in a showcase put on by This American Life, held at the Brooklyn Academy of Music on June 7, 2014.
The show opens with the story's narrator telling the audience about a plan called 'Operation D-Minus.' He introduces the story's hero, Justin Laboy, who is an eighteen-year-old senior honors student attending Park Vista Community High School in Lake Worth, Florida.
In Justin's final semester, a beautiful Puerto Rican-Dominican girl by the name of Naomi Rodriguez appears in two of his classes. Justin is instantly smitten by everything Naomi does.
He begins to go out of his way to make Naomi fall for him, repeatedly asking her, in person and in text, what he needs to do to make her fall in love with him. She won't "be straight up and just tell him what the heck [he] gotta do to be with her" no matter how much he texts her. Justin and Naomi soon become close friends, and Justin asks Naomi to go to prom with him. 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")
Naomi confirms to the Narrator that she was asked to prom but denies ever telling him she would think about it. The Narrator then reveals that Naomi is actually a twenty-five-year-old undercover cop working for the Palm Beach Police Force. Her assignment is to pretend to be a senior and discover which students are dealing drugs.
After explaining to the Narrator that she did everything she could to stop Justin from asking her to prom, Naomi goes up to Justin and asks him if he smokes. Justin tells her he doesn't, but if that's what she needs to go to prom with him, then he'll get her weed. He then divulges to the Narrator that he has no idea what he's doing, but he just cares too much about Naomi to have told her no ("One School").
Justin then goes on a mission to find Naomi weed. He calls a cousin, who in turn calls up a seemingly endless cycle of other cousins and friends in an attempt to get Justin the weed. Three cousins in particular argue over if they should help Justin or not, and are surprised that he would even ask such a thing due to the fact that he's such a successful student. Meanwhile, Justin is hounded by Naomi who keeps asking for the weed.
Eventually, Justin is able to convince his cousins to get him the drugs by telling them that he's in love. One of them hands Justin a bag of weed pellets, and he goes off to find Naomi ("Cousin").
Justin tries to meet up with her as soon as he acquires the weed, but she convinces him to meet at the school the next day instead. He slips it into Naomi's purse, and she tries to give him money. Justin refuses, insisting that the weed is a gift to her to prove just how much he cares about her. Knowing that she can't properly bust him without the sealing the deal with a monetary transaction, she shoves it into Justin's hands just as the teacher comes into the room-keeping him from returning it to Naomi and kisses him. ("The Money").
As soon as the deal is completed, the Narrator explains that Justin would soon find out that it's a felony to sell marijuana in Florida. Selling it on school property is even worse, and since Justin is eighteen and legally an adult, he had made an "irreversibly bad decision." Naomi reiterates that she's doing the right thing, though she seems to be upset about what she's done. She explains that there are smart and defenseless kids that she thinks about after the job is over, obviously talking about Justin.
In May, the police arrest thirty-one Florida high-school students who sold weed to undercover cops. One of them was Justin. He tries to argue, but in vain, as they have all the proof they need from his texts with Naomi. Justin realizes that he'll lose in court, and pleads guilty to the felony. 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.
Later, Naomi sits with the Narrator and discusses the effects drugs have had on her family. She reaffirms that she's doing the right thing, and wishes that someone had done her job when she was in school. However, she admits that she's never going to forget Justin, and that he did touch her.
During his time in jail, Justin can't stop thinking about Naomi. The Narrator asks Justin what he would say to Naomi if she was in the room with them. Justin responds, echoing his earlier sentiments: "What the heck did you do?" ("Epilogue").
The show is performed in one act, and is only fourteen minutes in length. The characters of the students, cousins, and cops are played by three ensemble members. The order of characters is the order of the character's importance to the song."What the Heck I Gotta Do" – Justin, Narrator, Naomi, Tevin, Derek, and Andrew
"One School" – Naomi, Narrator, Justin
"Cousin" – The Cousins, Justin, Narrator, and Naomi
"The Money" – Naomi, Justin, Narrator, Tevin, Derek, and Andrew
"Epilogue" – Narrator, Naomi, Justin, Cop, Lawyer, and Boy