Three boys and a girl giddily exit a fancy school. Judging by the suits and the girl's ruffled lavender party dress, they're on their way out of a school dance. It's raining and one of the boys opens an umbrella and holds it so the girl can stand under it. They all get into a car.
The boy in the pink polo shirt, Rolader, goes into a liquor store. He sets two bottles of champagne and a bottle of vodka on the counter. The clerk knows the kid is underage and asks for his ID. The kid offers the clerk $100 in lieu of ID, which the clerk accepts. The kid also picks up a package of that party essential: red Solo cups. On a yacht tied off at a marina, the boys pop the cork on the champagne and pour the girl a glass. They're all laughing and having a great time.
The next day, a little boy on a bicycle is doing his paper route and finds a teenage girl's body in a ditch. There's mud all over her and she's wearing a silk lavender dress, so we immediately know it's the girl from the dance. At the Chapel, Jenko briefs his team on the victim. Her name was Kim Morgan and the cause of death was alcohol poisoning. She had a stamp on the back of her hand from a dance at West Chadway Prep School. She left the event with 3 senior boys and that was the last time anyone saw her alive. There were possibly drugs in her system, but the tox report is still pending.
Doug and Tom will be going undercover to West Chadway as transfer students from another prep school. "Tom, for once, you got the right duds," Jenko remarks. Doug's facial expression says he's clearly not looking forward to this assignment. Can't say as I blame him either; if there's one stereotypical student I can't stand, it's the snob.
At West Chadway, Doug and Tom are given a tour by the headmaster. The school is "coordinate" but there's a separate girls' wing of classrooms for some reason. There's a common student lounge called The Hut. Doug looks extremely goofy with a relatively conservative haircut and the prep school's coat-and-tie uniform.
As always on Jump Street assignments, their first class of the day is English. At West Chadway, the subject is taught by a pompous British man in a cardigan. Doug quietly asks Tom what the hell "AP English" means. Tom explains the concept of Advanced Placement courses. The exchange was later appropriated into the movie version, where one officer asks his partner what "App Chemistry" is.
Class begins. The boys have been assigned to read All the King's Men. The teacher starts a discussion of the opening chapter. Doug surprisingly answers the teacher's first question correctly. Tom interprets the book's imagery of tires slipping onto the shoulder of the road as a lesson to not drive long-distance without resting. He is roundly mocked by the other boys, who begin chanting: "State College!" Apparently at West Chadway, that's a terrible insult. A weasel-like blond boy, Crowe, counters with an interpretation that satisfies the teacher.
In the hall, Doug tells Tom that he answered the question right through sheer dumb luck. All the King's Men was the only book he actually read at his last school. Doug hates the school because all the kids think they're smarter than everyone. Tom points out West Chadway's average college board score was 1300; however, he doesn't know if that's good or not 'cause he's apparently headed for State. Doug tells him there's nothing wrong with state colleges because his brother went to one. Doug has a brother?
Tom tells Doug to hang back and follow his lead because these are Tom's people. Doug rolls his eyes and says, "Tom Hanson: born to prep." On the stairs, a boy named Cary informs his friends Rolader and Crowe that Kim Morgan is dead. He's worried about it being investigated. The others are too.
At the Hut, we see that the girls at West Chadway don't have to wear uniforms, which makes no sense whatsoever. The Hut looks like a bar, right down to the little bowls of peanuts on the tables. Very weird. Doug flirts with a girl and ends up trying on her earring. Crowe, Rolader, and Cary join them. Doug sends Tom for drinks and tells Rolader he should get his ear pierced too. Rolader's girlfriend agrees it would look good. "Great," says Doug, "hand me that fork." Not sure if using a virgin pin would be better or worse.
Rolader's girlfriend asks Doug if he was kicked out of Westminster Prep because of his earring. Doug says he and Tom got in trouble for violating the honor code. The rich boys are disbelieving that goody two-shoes Tom would do such a thing. "He's really quite corrupt when you get to know him," Doug assures them.
Meanwhile, Judy is at a modest home interviewing Kim's mother. Mrs. Morgan feels guilty about letting Kim go to so many parties and admits her daughter was difficult to handle. Kim wanted to marry money despite her mother's warning that "those boys don't marry anyone from the East Side." I'm starting to get an Outsiders vibe from all this, especially when Kim's greaser-looking brother Vinnie appears.
Vinnie is sullen and thinks the case is gonna be swept under the rug. Judy asks if he knows anything that can help; Vinnie doesn't know anything other than "3 rich boys got my sister so drunk that she died."
Rolader, Crowe, Cary, and Doug drink Absolut vodka on the rocks in someone's living room. We have a saying at my college that goes: "Vodka effs you up, Absolut effs you up absolutely." Anyway, Crowe proposes a toast to the Fun Club: "thrill-seekers, risk-takers, and wealth-makers dedicated to competition and recreation." Judging from the lines of coke on the coffee table, "recreation" equals recreational substances.
Doug pretends to snort some coke and offers up Tom's house for the club's next meeting. A drug dealer named Kurt shows up with a briefcase full of money and wants them to make another drug run that week. Crowe doesn't want to until after mid-semester break because they have too much homework. Aren't we good little students?
Kurt wants to know about Kim's death. The boys partied with her on Kurt's boat and apparently made quite a mess. When he leaves, Rolader tells Doug that he has potential. He offers to initiate him into the Fun Club. Crowe tells Doug to find his passport so they can all "go on an adventure." Which is probably to Bogota.
Judy isn't so sure that Kim was murdered. Doug automatically assumes that there wasn't a rape either; Judy gets defensive. Doug says the guys don't strike him as murderers. People said the same about Ted Bundy...
Tom voices his opinion that Doug hated rich kids until he had a chance to be one. Doug counters that he knows the Fun Club better than Tom; Cary, Crowe, and Rolader think Tom is a dork and won't let him hang out with them.
Jenko stops the argument only to have another break out. "Kim Morgan may have just been a party animal who died in the woods," Doug says. Judy stands up and demands: "So only good girls get raped? Is that it?"
Doug turns his attention back to Tom. He had to arrange for them to meet at Tom's house to keep him in the loop. Jenko hands down his case strategy. If they're wrong about the murder/rape, they'll bust the boys for the drug smuggling. He tells Doug to go along on their buying trip. Harry asks why kids with rich parents would bother running drugs and Doug sums it up: "No risk, no rush."
At The Hut, the boys plan out their trip to Puerto Vallarta. I guess Bogota would've been too cliche. They can't take Tom because the private plane only seats 4. Crowe suggests "they assemble for cocktails" at Tom's when they get back. Tom goes to Jenko's office with the worry that the house won't be fancy enough. It will be; they got it from a sports car designer who had his assets seized by the IRS.
Judy visits Vinnie at the garage where Vinnie works. He knows about the 3 boys now because he broke into his sister's diary. He still thinks his family isn't rich enough for anyone to care about Kim's murder.
The private plane with Cary, Rolader, and Crowe aboard lands at the airport. Tom is waiting in a limo. Harry is with him, dressed in a chauffeur uniform. The Fun Club made Doug fly back commercial so they wouldn't run the risk of Daddy Crowe's plane being seized.
Doug meets them in the main parking lot dressed like a stereotypical tourist: goofy hat, Hawaiian shirt, and khaki shorts. Tom bosses Harry around for a while before he and Doug get in the limo by themselves. The rest of the Fun Club will follow in their own limo.
In the backseat, Doug tells Tom that the trip was fairly uneventful. Except for the part where Doug walked through Customs with a kilo of cocaine in a false-bottom suitcase. Tom is not happy; now they won't be able to bust the boys for drugs because Doug is technically an accomplice. Doug didn't really have much choice, but that won't matter to a judge. Doug tells Tom to shut up because he feels bad enough. Harry informs them that Kim's body showed signs of rape.
Kurt comes to "Tom's" house to pick up the merchandise. Tom and Judy follow Kurt to bust him for possession. They see him proposition a hooker. Turns out the hooker is a Vice detective. He's taken and booked into the 77th Precinct, which is run by Jenko's old rival Jacobson. Jenko goes to get Kurt out.
The Fun Club talks to a lawyer (one of their uncles, not sure whose) about bailing Kurt out of jail. They mention Kim Morgan and their worries that Kurt will roll over on them.
When Jenko learns Kurt made bail, he asks Judy and Harry to follow Kurt. They do, eventually arresting him. In the interrogation room, Kurt insists he doesn't know a thing about Kim. Doug plays "bad cop." He grabs Kurt by the front of his shirt and asks him how much the boys paid him to go to prison for something they did. He leaves.
Outside, Doug tells Tom that when Kurt finishes doing 2 years for possession, "I'm gonna be waitin' at the gate wit' a bat." Ah, the old Italian tough-guy routine. He thinks the rich kids' feelings have been bred out of them and all they do is compete. It's possible. Where I live, people say the same thing about Thoroughbreds.
Doug kicks in the door of a very nice house, the same one where the first Fun Club meeting took place. Doug goes into the living room closely followed by Tom. Crowe somehow knows they're cops. When the boys gets snotty, Doug tips over the coffee table they were doing lines off of. "We should've anticipated that," Crowe deadpans. This is funnier than it should be.
Doug and Tom tell the boys that Niles will roll over on them. The boys aren't worried. They say the cops are bluffing. Eventually, Tom and Doug admit that they are, in fact, bluffing.
Rolader cracks and goes to the police station to confess what really happened to Kim Morgan. The catch is that he wants immunity. When that news arrives at Jump Street Chapel, the cops bemoan the fact that Rolader got to walk free.
But not for long. Vinnie shows up in the parking lot of West Chadway, leaning against Rolader's car. He demands to know what Rolader and the others did to Kim. Rolader smirks. Vinnie shoots him. Karma will get ya every time...