Films Featuring Teens on the Make (Like Gary From ‘Licorice Pizza’)

In Licorice Pizza, Gary (Cooper Hoffman) always has a plan. He is constantly on the make, whether acting, selling waterbeds, or opening the first pinball alley in LA the moment prohibition ends. In the world of Licorice Pizza, that makes him stand out. He’s a teen entrepreneur, a hustler without a peer.

However, in cinema, he would find contemporaries who could relate. Adolescents always trying to pull the next score, teens searching for that angle. Whether they’re overachieving academics or outright criminals or dancing somewhere in the grey in between, they are part of the exclusive club that claims Gary as their most recent inductee. Love Licorice Pizza and want to find more characters like Gary? We have them here in the films featuring teens on the make.

Rushmore

Max Fischer (Jason Schwartzman) is…odd. At 15, he seems to involve himself in every extracurricular activity at Rushmore Academy. He nets less than stellar grades, but who wouldn’t they were as busy as Max?

Max takes it even further when he becomes infatuated with Rosemary Cross (Olivia Williams), an elementary school teacher at the Academy. Extracurriculars give way to building a giant aquarium, blackmail photography, and cutting people’s brakes. With the internet in play, things escalated quickly.

Regardless of what mode Max finds himself in, whether overachiever or sociopathic wooer, he makes things happen. Not always things anyone wants to have happen, perhaps, but things nonetheless. Who else can nearly kill a man one week and mount a massive play about the Vietnam war with only high school students the next?

Easy A

Olive Penderghast (Emma Stone) has great parents, Rosemary and Dill (Patricia Clarkson and Stanley Tucci)—seriously greatest of all-time parents!—a cute brother Chip (Bryce Clyde Jenkins), and a best friend, Rhiannon Abernathy (Aly Michalka). But she doesn't have much going on in the romance department. Nonetheless, when her best friend leaps to the conclusion that Olive had a hook-up one weekend with an older college guy, Olive doesn’t correct her.

A minor lie, perhaps, but one overheard by the gossipy, very “Christian” Marianne Bryant (Amanda Bynes). Marianne decides to dedicate her life to “saving” Olive, primarily by shaming her repeatedly. In response, Olive decides to go all-in on the rumors of her promiscuousness.

For classmates who need to cover up for their sexuality, gain social cache, or cover for some other indiscretion, Olive begins to sell her services. She’ll let them say they copulated with her in exchange for gift cards. She took the world’s oldest profession and adapted it for the rumor-riddled high school years.

Risky Business

Speaking of hooking, Joel Goodson (Tom Cruise)—not the subtle surname—decides to forgo the whole “adapt it to the era” thing and just go right ahead with the traditional version.

A high achiever trying to secure a slot at Princeton to impress his dad, Joel seems like the kind of kid who’d never take a sip of his father’s beer, never mind raid the liquor cabinet. Still, when his parents go away, he lets his less scrupulous friend Miles (Curtis Armstrong) convince him to abuse the privilege.

The first night brings some standard shenanigans—“borrowing” dad’s sports car, turning up the stereo as loud as it will go, dancing around the house in his underwear—but Miles finds no satisfaction with such vanilla misbehavior. So, like any average 17-year-old, Miles calls a working girl for his best friend. You know, like kids in the ’80s did all the time.

Eventually, Joel connects with Lana (Rebecca De Mornay). Unfortunately, their first night sets off a series of events that puts Joel in conflict with Guido (Joe Pantoliano), a pimp. Facing massive car repair bills, a missing Fabergé egg, and several items stolen from his home, the teen decides to beat Guido at his own profession.

Joel converts his home into a suburban brothel with the help of his friends, Lana, and several of her fellow street walkers. Being the overachiever he is, he turns out to be very good at it. Again, just a typical ’80s experience.

The Girl Next Door

What is it with teenagers and fornication work? Well, as long as we are on the topic, we might as well keep going.

Matthew Kidman (Emile Hirsch) is ready to graduate high school at the top of his class. However, he feels nothing for his high school years. Despite his success and having friends, he’s certain he hasn’t experienced anything memorable.

However, when 20-something Danielle (Elisha Cuthbert) moves in next door, that starts to change. The two begin a relationship that sees Matthew open up and act spontaneously or recklessly—depending on viewer valence—for the first time.

The revelation of Danielle's film career causes some strife as Matthew reacts with implicit misogyny and fornication-negative judgment. While he manages to make amends, doing so attracts the attention of her ex and former producer Kelly (Timothy Olyphant). As with Guido above, Olyphant decides to ruin the teen boy’s life. In response, Matthew does the only reasonable thing. He teams with a different adult film producer and goes into the industry himself.

Without spoiling the film entirely, Matthew proves as adept at risque photography as he does at school. Moreover, his solution to his problems turns out to be a massive win-win for basically all—save Kelly—involved. Teenagers surrounded by adults who would rather pretend fornication doesn’t exist, especially benefit.

Catch Me if You Can

Everyone else on this list accomplishes tremendous and impressive things. However, none started drawing paychecks from a major airline at 15. But Catch Me’s protagonist, Frank Abagnale Jr. (Leonard DiCaprio), sure did.

Abagnale takes “teen on the make” to its absolute extreme, defrauding various businesses of millions of dollars throughout his crime spree. A gifted con artist, he repeatedly outthinks the FBI, passes the Bar exam despite never taking a day of law school, and convincingly impersonates a Secret Service agent. His wheeling and dealing got him more than anyone else on this list, but it also brought him far worse consequences. This is a “teen on the make” movie for those wanting something a bit heavier on the pathos. In particular, viewers get to see some darker results for the precocious adolescent at its center. It also features DiCaprio at his most slippery charismatic.

The Wackness

It takes a particular breed to see a therapist and then be that therapist’s drug dealer. Luke Shapiro (Josh Peck) belongs to that specific breed. Initially just trading marijuana for therapy with psychiatrist Dr. Squires (Ben Kingsley), events soon conspire to force Luke to take the dealing more seriously. With his parents facing eviction and no money for college, he has no choice but to commit to the criminal enterprise fully.

Unfortunately, he also keeps getting distracted by his feelings for his psychiatrist’s stepdaughter Steph (Olivia Thirlby). Negotiating his infatuation, his ill-advised choices with substances, his enmeshment with Dr. Squire, and his parents’ economic woes pull Luke in opposing directions.

The Wackness exists as something of a counter-narrative to many of the other “teen on the make” films. Josh is unquestionably competent, but reality limits his machinations far more than, say, Joel Goodson’s incredible successes. In Wackness, Lucas’s ability to adapt and run his business feels more like skills and less like superpowers.

Ferris Bueller’s Day Off

Ferris Bueller’s (Matthew Broderick) plotting and planning seem both weirdly low-stakes and wildly over the top compared to others on this list. Ultimately, he just cuts school for the day using a tape recorder, some pillows, and his wit. However, that he takes those modest skills and that relatively low-key goal and ends up in a parade lip-synching for thousands is an undeniably impressive escalation.

Recent years have been less than kind to Ferris. Viewed at the time as a lovable scamp involved in a delightful day-long romp, many these days tend to label Bueller as something more akin to near sociopathic and his antics as profoundly unfair and unpleasant. Regardless of a viewer's particular lens, though, Day Off is undeniably well-paced and entertaining. Even horrifying people can amuse in film, after all.

Election

If Max of Rushmore had a public-school twin, Tracy Flick (Reese Witherspoon) would be that cousin.

Ambitious, overprepared, and overinvolved, she belongs to every club and plans every event. While not especially well-liked or popular, Flick keeps moving forward, goal-driven and unapologetic.

Election, however, is the rare film that casts this teen on the make as the lead’s antagonist. Rather than make Tracy the POV character, viewers observe her through history teacher Jim McAllister’s (Matthew Broderick) eyes. Thus, audiences feel repulsed instead of delighting in her antics as viewers would typically do with films in this subgenre. Her ability to assert her will on the world isn’t celebrated; it’s denigrated. She’s not a charismatic delight; she’s a strident self-involved annoyance.

And yet, she still wins and vanquishes the increasingly unhinged and morally compromised McAllister. In an inversion of how some people have come to view Ferris Bueller as selfish and awful, distance has given many viewers an appreciation that the Flick we see on-screen is likely filtered through a teacher’s judgmental eyes.

Pump up the Volume

Unlike everyone else on this list, Mark Hunter (Christian Slater) doesn’t want anyone to notice his activities. Well, he wants them to notice, but he doesn’t want anyone to realize it’s him.

That’s why he’s conducted his pirate radio program under the aliases of Hard Harry and Happy Harry Hard-On. He’s an ambitious teen with plenty to say, much of it amorous, but he has no interest in getting recognized for his work. Instead, he wants the work, not himself, appreciated.

The radio station alone might qualify him on this list, but Hunter doesn’t stop there. After connecting with a fellow student but not being able to dissuade him from pondering suicide, Mark banks hard into taking the job more seriously. He starts talking more honestly about life as a teenager and urges his listeners to resist conformity.

Before long, he becomes so successful that the FCC and local police begin to search for him. Not bad for a kid who started just wanting to spin records and talk about his erection a lot.

Charlie Bartlett

Charlie Bartlett (Anton Yelchin) has gotten kicked out of many high schools by the time we catch up with him. He’s come to the proverbial end of the line, and, despite his family’s ostentatious wealth, he must now attend his local public high school.

Initially, things go quite poorly. The private school blazer, briefcase, and general demeanor mark him for bullying when he shows up on his first day. However, he refuses to let the mockery and beatings drag him down, and before long, he’s connecting despite the odds.

Like Gary, Bartlett can’t help but see business opportunities everywhere he looks. This leads him to team up with school bully Murphy Bivens (Tyler Hilton) on several business endeavors, including selling videos of Murphy attacking fellow students. However, the real breakthrough comes when Charlie sets himself up as the school therapist, offering counsel and feigning ailments to his psychiatrist to bring those medications to school for classmates with the symptoms.

Becoming something of a mythic figure at school, Charlie also begins to become key to agitating against changing rules and helping kids realize their goals. Unfortunately, he’s also making choices and engaging in activities no teenager should, and with dire consequences. Can he recover and find a new way to keep helping his classmates and friends?

Don't Tell Mom The Babysitter's Dead

Ok, so Swell Crandall (Christina Applegate), the teenager at the center of this 90s cult movie, doesn't start out as a 17-year-old trying to succeed in business. Happenstance, however, puts her in charge of providing for her siblings, not to mention disposing of the body of a tyrannical babysitter who happened to die while on the job. To make ends meet, Swell impersonates a recent college grad and enters the fashion realm, becoming an influential assistant at a major design house. 

We include here because Swell survives by her wits, much like the other vibrant characters mentioned here. It also helps that Christina Applegate gives one of her best performances in the lead.

The Garbage Pail Kids Movie

Lord, help us all. Let's be clear here: The Garbage Pail Kids Movie might actually be the worst movie ever made, and if not, it comes dangerously close. 

That said, the movie does feature some teens on the make: Dodger (Mackenzie Astin) and Tangerine (Katie Barberi), who put together their own fashion business with the help of the titular…creatures. And that, kids, is the only redeeming quality of this mess of a movie.