The film opens with Tobias “Toby” Hammel (Thomas Mann) at the airport looking a pretty girl on the escalator in front of him.
“My name is Toby,” he narrates. “I’m seventeen years old. I’m a scholarship winner, and I’ve started and ran an international drug ring. And I am fucked.”
THREE MONTHS EARLIER
We see Toby in his car driving onto the campus of his new school. It is September 1984. Toby says it is Sage Hall, an area that while not far from his home, though it might as well be a different country. He notices the various rich kids, who he labels “preppies” who dress well and seem to have their lives pre-set to greatness because they usually are, given their money and connections.
We see Toby at home with his mother, Ingrid (Amy Hargreaves) and his father Michael (Bill Sage). Ingrid checks the mail and sees that Toby has been accepted to Sage Hall. Toby tells her he didn’t apply since he knew they didn’t have the money, but Ingrid says he has been given a scholarship to attend school there. Ingrid says she is so proud of him, as is his father. Toby narrates to the audience, saying his family line on his mother’s side apparently was rich, but being on the “wrong side” of the Berlin Wall made them lose everything. His mother never stopped hoping for better things for her son, and thought going to Sage Hall would change his life. Toby says that it did.
Toby however, feeling the strain of being a lower class kid, skips out on registration day. That night, his mother is livid with him for missing out on the opportunity, and Toby lies, claiming he couldn’t find the right building. Ingrid tells him that she smoothed things over with the administration, saying she will personally bring him over to Sage Hall to register the next day. Michael, realizing his son was uncomfortable, asks what he wants. Toby says he doesn’t feel like he belongs there. Ingrid says he doesn’t know where he belongs, and that he will thank her one day. Toby says they can’t force him to go, so his mother leaves the dinner table in a huff. Later, Toby relates that when things got bad, his mother would watch TV for nights in a dark room. Her depression only would end when he offered something. Toby lies next to her and says he will show up the next day. Toby tells us he did it for his parents, knowing they only want what is best for him.
The next day, Toby is late for an opening ceremony of the class. He tries to stay in the back, but the elitist kids keep him from sitting down, forcing him to sit in the front. After the speech is over, Toby, along with everyone else is required to sign an honor code pledge in a ledger that has been in the school’s history for over 200 years. However, when it is his turn to sign, the pen doesn’t work, and he splotches ink all over the ledger. His attempts to fix it cause him to knock the ledger over along with himself, embarrassing him in front of the entire student body. A boy, Fidel (Guillermo Arribas), who is sympathetic to Toby, introduces himself.
Toby tells us Fidel was from Columbia, but his racist and ignorant classmates call him “The King of Mexico.” Toby realizes that Fidel desperately wants a friend because like him he’s an outsider too. Fidel tells him that his father is a diplomat, and comes to the U.S. rarely. Toby tells Fidel his father is a deliveryman, underlying his gap of familial success even to a supposed outsider like Fidel. Fidel shows him around campus and Toby sees Alex Hayes (Lucy Fry) and is struck by her beauty. Toby is shown to his dorm, but as a day student, he only attends the school, but does not live on campus. A young man, Ellis (Logan Huffman) comes up to Toby and asks if he wants to share a smoke. Toby says yes.
Toby tells us Ellis is the fourth generation to go to Sage Hall and his father apparently was friends with Ronald Reagan. Toby says Ellis had charisma and he immediately felt like he wanted to be his friend. Ellis notes he trashed a book that his father and other descendants had their names in. Toby apologizes but Ellis brushes it off and tells him he thinks it was kind of cool. Ellis asks if he has seen the TV longue yet. He brings Toby there, where several other students are hanging out. As Toby is distracted by the TV, someone pulls a sheet over his head. Ellis and the other guys strip Toby and beat him mercilessly. After a few minutes, Fidel comes in and pretends that the headmaster is coming in, making the boys flee. He pulls Toby up and gives him some pointers for blending in, including how to dress, and unspoken social rules. He also tells Toby he has been christened with the nickname “Flipper” due what he was watching when he was attacked.
Toby gets to his ECON class late. He is saved though by knowing exactly what his teacher, Mr. Jennings (Sam Page) was talking about when he walked in. Toby says Mr. Jennings saw him as a pet project after he fell off the stage. Ellis pretends to cough and calls Toby “Flipper” to the laughter of the class.
Later, Toby notes he began to take in everything around him, in order to seamlessly blend in more, and forget his past. However a part of his past, his best friend Dennis (Dylan Blue) arrives on campus to catch up with Toby. Ellis and his friends are rude to them at a distance, to the point that even Alex, who is apparently dating Ellis, tells Ellis he is being a dick. Ellis asks a friend if he has any weed, and the friend tells him no.
“And then it happened,” Toby states.
Alex stands up and walks over to Toby. She reaches up and grabs the tag he left on the shirt and pulls it off. “I will never forget the back of her hand against my neck,” Toby says. Toby introduces himself, but Alex says she knows, as they have ECON together and he made them all look stupid the other day. Alex asks if they have any pot. Dennis and Toby say no, but Dennis says he can get some for 45 bucks. Alex says that is quite high, but Toby notes, “Ellis can afford it.” Alex, convinced, gives him the money. Toby says he will let them know.
Toby notes, however, neither he or Dennis had no connection to weed, but he was determined to find one if it gets him closer to acceptance. Toby and Dennis spend the night searching for dealers until they finally get one. Toby brings back the pot to the group and he tells them the story while they smoke. Toby relates to the audience about the second couple of the group, Laura (Jessica Rothe) and Ben (Robert Gorrie). Toby says Laura was sweet and always kind to him. Ben was a prick but Toby still liked him. Though he was a fifth wheel, Toby says it felt nice that he was talking and the group were listening to what he had to say.
Suddenly, there is a knock at the door. Ellis, Alex, Ben and Laura escape out the window while Toby is left in the room to face Mr. Gaines (Nat DeWolf). Toby shuts the door and lets the others, especially Alex escape. Toby says he would block a train for her. Mr. Gaines, realizing something is up, ushers Toby out.
Cut to Toby at home with his mother Ingrid crying and his father Michael stoic. Toby has been suspended for the weed. Toby says he’s sorry but his mother leaves the room, devastated that he is throwing away his good fortune. The next day, to punish him, she makes him do lots of yard work. Alex shows up at his home, saying she heard what happened and wanted to come by and see him. His mother comes out and tells him to get back to work. Toby lies and says Alex is a Girl Scout selling cookies. Alex thanks him for his sacrifice for her and her friends.
Toby returns to school after his suspension, and now everyone wants to know him. The pot incident had become urban myth and the preppy elite were appeased by his willingness to keep his mouth shut. Ellis speaks to Toby and thanks him, inviting him to come with a few of his friends at midnight at the golf course. Ellis tells him not to be a pussy.
“Don’t be a pussy,” Toby narrates as we cut back to him at the airport, with a large duffel bag, apparently full of drugs. Toby says he came to find he wasn’t afraid of anything, except losing her. We realize the pretty blonde in front of him is Alex.
Toby meets up with Ellis, Alex, Ben, and Laura, who make cocaine lines on a book. Everyone does one line except for Toby. Alex guesses he hasn’t done it before. “Come on Toby, it’s not gonna hurt,” Alex says. At her insistence, he does a line, and the group devolves into a drug stupor. Later, Toby asks why cocaine is so hard to get. Alex replies because everyone wants it. Ellis notes you need connections. Toby says he can get more. Ellis dismisses his claim, but Alex thinks otherwise. “If anyone can get it, Toby can,” she says which Toby notices. The group then breaks off. Toby and Ben strip and enter the cold pond to swim with laughing watching and laughing. Meanwhile, Ellis and Alex run around in a field before falling to the ground. Ellis tells Alex he is in love with her, with Alex replies that she knows. They kiss, and presumably have sex.
Toby comes home, late, and his parents are waiting for him to ask where he is been. Toby deflects their questions, saying they need to leave him alone. Michael tells his son he can’t afford any more trouble after being suspended. Toby replies that they apparently can’t afford anything, cutting his parents to the bone over their lack of money. Toby goes into his room and has a panic attack, tearing photos off his wall. He knows he is a poseur and a pretender to these kids. All he wants is to belong. In desperation he calls up Dennis for help.
Dennis arrives later, bruised from a drug deal that went bad. However, he was able to steal a small amount of cocaine. Toby is able to sell it to an impressed Ellis. Toby tells Dennis they need to get a lot more.
Toby spends more time with Fidel, constantly asking about Columbia, eventually convincing him to take him on a trip to see his family. He asks about cocaine, and where to get it. Knowing how much he wants to belong too, in order to make Fidel help, Toby convinces him that by getting the cocaine, he can get Fidel into Ellis’ group. Fidel is swayed and his family pays for a ticket for Toby to come. Toby pools money from Ellis, Laura, Ben and Alex to make a big buy, three thousand in total. Toby researches Columbia heavily, learning of the drug cartels, the violence, and numerous politicians and journalists killed in the drug war. Toby says he didn’t care, for he was excited about what he was doing.
Toby and Fidel were watched by a bodyguard at all times, who only let them travel to specific safe places around town. With Fidel distracting the bodyguard with haggling over an item, Toby runs off to find a cocaine connection. He goes into a bar and gets a beer. He then heads into a bathroom and hides the money in case he gets mugged. He goes out to a group and asks if they know about getting cocaine. They pretend to agree, and then proceed to beat him in an attempt to rob him. The bartender stops them and pulls him up, showing him the money roll, telling Toby it was a smart move, but not smart enough. Toby asks why he didn’t keep him and kill him. The bartender says that cocaine is his true business, and he loves American customers. He tells Toby to come, and they do business.
Later, the bodyguard is chewed out for losing sight of Toby, who lies and say he was mugged. He tries to take full responsibility saying he went off on his own, but Fidel’s father is having none of it. Fidel later tells Toby what he did was stupid and he never wants to lie to his parents like that again. Toby and Fidel head back to the U.S. with Toby declaring the statue he had bought for Alex as the only thing to declare. When the Custom agent asks what he did in Columbia, Toby lies and says he went to lose his virginity. The Custom Agent smirks and lets him through.
Toby says many students were not back at Sage Hall from the long weekend. Alex was, as her parents were never around at home anyway and thus stayed in the dorm for the solitude. Toby shows up at her room and shows her the statue, which he proceeds to break open and show the cocaine he bought with their money. Alex is stunned. “I can’t believe you did it,” Alex says.
Toby shows the group what he bought, an eighth of a key. Ellis takes a bump, and can’t believe it is a pure sample, with no mixers to dilute the purity. Toby notes there are many schools that could want drugs of this quality. Ellis offers to buy the rest but doesn’t have the money yet, so Toby tells him no. A knock on the door startles them, but is only Fidel. Toby shows him the drugs and asks if he wants to party. Fidel rushes out in a panic and Toby pursues him. Toby asks him what is wrong, that he thought Fidel wanted to be part of the group. Fidel tells him he wanted no part, because as a Columbian he is an easy target to be arrested for drug smuggling. Fidel only wanted a friend, and he realizes Toby just used him as a pathway to drugs. Fidel says Americans are all alike; they only use people. Toby snidely says that Fidel can be so self righteous when he has so much. Fidel calls him out for his real reasons for getting drugs; he is obsessed with Alex. Fidel tells Toby he will never have Alex; she will use him and then spit him out.
Toby is at home one night when he hears his parents arguing over money problems. He realizes how hard they are struggling, and realizes he has a means to help. He narrates that he bought 125 grams of cocaine. He made a deal with the preppies that he got to keep half of it or sixty two grams to himself. He gets materials to mix the pure cocaine with, to increase the amount he has. He then proceeds to sell it at 50 bucks a gram, hoping to make six grand. Word spreads, and Toby becomes quite popular. Ellis still offers to buy it whole sale, but another kid says he knows people that will pay upwards of double of what Ellis can offer.
Toby and the kid go to a party. Toby notes he wanted to belong, but became something better, their dealer. He no longer needed invites to parties; he was the party, and thus exerted control over those who previously looked down on him. Toby makes a deal with a man for all he has on him. He sits in the den, smoking pot while a couple has sex on a couch next to him. He notices a man next to him. It is Mr. Jennings, his teacher, who recognizes him.
Toby asks what Mr. Jennings what he will do. Mr. Jennings says he likes Toby, and finds him very smart. However, it warns him of the danger he is in. If Toby is caught, he will not have the means to get out of trouble like his rich classmates would. Mr. Jennings says they didn’t see each other that night. Toby says that was fine for him, but unlike what Mr. Jennings thought he was going to keep going and sell it all. Toby fakes a letter from his uncle to his mother, claiming to send money to help them, giving his parents all the cash he made.
One day, while dealing, Alex approaches him. He shares the last bit of his drugs with her. At his urging, Alex recites a poem she had to speak in class. Alex tells him Ellis is having a party at his parent’s apartment and he can come if he can score more drugs. Toby says he will just go back to Columbia, and can be back in 36 hours. Alex says they can cover for them, as Ellis can forge the attendance sheets. When the students learn of his new trip, money pours in as kids scramble to make orders. Toby packs up and lies to his mother, saying he is attending an overnight prep course but of course is actually heading to Columbia, make a deal, then get back before anyone notices.
Toby heads to a nightclub, and after being checked out, heads inside with a guard, so he can make a buy from Raoul, the bartender/drug baron he met last time. Raoul talks about plans for the next day, but Toby counters he has to return home, as he is still in school, which makes Raoul’s friends laugh at how young he is. Toby does lines with Raoul and his friends and talks about Alex. He admits that she isn’t actually his girlfriend as he stated, but wishes she was. However, she is rich, like her friends, and he doesn’t feel he is worthy of her, or that she would even go for a guy like him. Toby narrates that he perhaps said too much. Raoul tells Toby he will be rich soon enough.
Toby notes that Raoul gave him cocaine and didn’t even count his money, trusting him. Toby says the myth of guys with guns didn’t happen with him. Raoul made it fun even. Toby dances with a girl at the club, further entranced with his new life.
Toby goes back through customs again, apparently trying the statue again. The agent breaks the head off the statue, apparently busting him. However, we see Toby meet up with Alex and the rest of her friends. He saw that the statue trick would probably only work once, and especially not with the amount he was bringing in. Toby travels with the group by bus, and watches Ellis kiss Alex on the neck. But Alex looks at Toby forlornly and Toby can’t help but look at her even as she gets even more hot and heavy with Ellis on the bus.
The group gets to NYC, and with fake ID’s get into numerous clubs, going to a rock show. They go back to Ellis’ apartment, drink and do drugs. Ellis starts to notice how close Alex and Toby are and voices his concerns angrily, asking him if he is “making a play” for his girl. Toby tries to deflect, but Ellis says Toby is being too close with them. Toby tells him to calm down, saying they were just having fun. Ellis says okay let’s have some fun, and proceeds to throw a TV out the window, which lands on a car. Alex loses it, slapping him, screaming at him for his behavior, as he could have killed someone. “Don’t hit me,” Ellis tells her. “You don’t have the right.” Alex slaps him again, so he slaps her in response, Alex falling to the ground. Shocked, Toby and Ben pull him away, telling him to calm down. Ellis finally realizes what he did and apologizes profusely, leaving the room. Toby checks on Alex, who says she’s fine and she will look after Ellis. Laura, who has witnessed all this, realizes what the drugs are doing to them and tries to stop her boyfriend Ben from doing more, which he refuses to. Laura storms out of the room, while Ben does another line of cocaine.
In that moment, Toby’s illusion shatters. He realizes he has nothing. These people are not his friends. He is nothing more than a servant to a bunch of “sad, rich orphans.”
Toby continues to sell drugs, do drugs, and send money to his mother under the guise of his uncle’s help. However, this eventually starts to catch up with him, and his teacher Mr. Jennings notices. He confronts Toby and tells him to stop what he is doing, but Toby tells him he is a hypocrite. Toby relates Mr. Jennings didn’t stick around for the potential fallout; he quickly resigned, knowing Toby was a liability to his future as a teacher.
Ellis and Alex are in his room. Ellis wants more cocaine, so Alex says he should go to Columbia like Toby did and buy it. Ellis says he won’t go with Toby, so Alex says she will go instead. Ellis vehemently objects to that, so Alex points out that Ellis is fine with Toby being on the line because he is the “mule” and because he thinks he’s better than Toby. Ellis firmly tells her she can’t go with Toby, and Alex says okay.
Toby’s recent antics are chalked up to a panic attack and his mother comes to get him. On the way home, they are stopped by Alex, who asks if it is okay if Toby accompanies her to Palm Spring for Thanksgiving, indirectly letting Toby know she wants to make another trip to Columbia. Toby tries to decline, perhaps realizing he is about to cross the line, but Alex pushes, and charms Ingrid with tales of her father’s connections to Senator Strom Thurmond and that the tickets would be free of charge.
Ingrid is convinced by Alex and buys Toby a bag for the trip from the drug money he had sent to her. His mother tells him to go on the trip and be with Alex.
The two of them get on a plane to Columbia. At the hotel pool, Alex tells him she got their room fares combined to get the Honeymoon Suite. “She was fucking with me,” Toby notes, because that was what she did with people. But Toby notes he didn’t care.
In their room, Alex mixes drinks while Toby plays the piano. Alex asks for him to play something, so Toby plays while singing some lyrics, which are somewhat directly linked to his desire to be with her, which makes Alex tear up at the realization. The two of them kiss, and eventually have sex.
The next morning, Toby gets a call from Raoul to meet in two hours. Alex and Toby meet him at a house party, and tells them to enjoy while he gets them drugs. Toby does drugs and dances with Alex but gets overwhelmed. Going outside, he hears Raoul arguing with some men. It turns out, Raoul has figured out (thanks to Toby) that Alex comes from rich a family and plans to kidnap her for ransom. When one man objects to the plan, seeing how Raoul botched a previous kidnapping, Raoul stabs him to death, shattering Toby’s picture of Raoul as an easygoing drug baron. Toby sees the bag of drugs, and grabs it, leaving the money. He grabs Alex and they escape, with Raoul and his henchman not far behind. They hide out in a house, and when Raoul sees the man who owns the place and asks about Toby, the man lies for them, allowing them to escape. The man gives them safe passage, and Toby pays him with a parcel of cocaine in gratitude.
Ellis comes to Alex’s house looking for her, only to hear she is away on a trip with a friend. Realizing that friend is Toby, Ellis asks to use the phone.
On the plane ride back, a shell shocked Alex tells Toby she has a very bad feeling, and recommends he throw away the cocaine before they get back through security. “We don’t need it Toby,” Alex says, having realized she likes Toby more than the drugs.
Ellis sits near the phone, and then finally makes a call to a Dr. Fielding, saying it is important.
Toby goes into the airplane restroom intending to flush the drugs, but he hesitates.
Back at the terminal, he goes up to Customs, and makes it through. However, as they grab their luggage and are about to head out the terminal, DEA agents swarm him and thoroughly check his luggage, finding the cocaine he did not flush away. Toby is arrested, while a heartbroken Alex is led away.
Ben and Laura speak to Ellis about Toby’s arrest and are fearful about being brought up on charges. Ellis reveals he is the one who got Toby busted because he called the headmaster Dr. Fielding and told him everything Toby was doing. Dr. Fielding alerted the DEA, which led to Toby’s arrest. Toby will go down, while the rest of them will get suspensions at most. When Laura asks about Alex, Ellis’ lack of response makes her realize that he sold Toby out because Alex chose to be with Toby instead of him. Laura leaves the room inconsolable, realizing the true nature of her supposed friends.
Toby is in court, while his mother sobs. The prosecution is charging him with Federal Drug Trafficking. His actions become a national news story and the press wants any part of the story they can get. 60 Minutes tries to interview Dr. Fielding over the epidemic of drugs at his school but he brushes the reporter off.
Laura, overwhelmed by recent events, tries to contact both her mother and father for emotional support, but they are too busy to talk to her, despite her pleas.
Dennis raids one of Toby’s cash drops before it can be recovered by the police.
Toby narrates that Laura went into the woods and disappeared for two days. The police found her, dead in a stream, an apparent suicide.
Ben tracks Ellis down and gives him the beating of his life, holding him directly responsible for Laura’s death. Ellis breaks down after, seemingly understanding the weight of his petty actions.
Toby has a conversation in jail with his parents. Michael says the judge wants to make an example out of him, but if Toby spends a little time in jail, perhaps he can get bail, though they will have to put up the house. Ingrid tells her son to give a full confession, give up every name, in the hopes of getting a reduced sentence. Toby tells her it was all him; he bought it, smuggled it in, and sold it. Toby asks about Alex; Ingrid tells him her father made a deal. If Alex stays in South Carolina, she will not be extradited on charges. Ingrid asks if he understands how rich people like her get away while he will suffer. Toby narrates that he understood a long time ago that he would always be an outsider, that he would never be let into their club, though his mother never could. Toby just asks if Alex is okay, which his father affirms. Michael then asks why he didn’t dump the drugs when he had a chance. Toby just says he is sorry and then has to leave.
As he walked back to his cell, Toby tells us the fates of everyone involved. His parents eventually divorced, with his mother feeling someone had to be responsible for what Toby became. Ellis and Ben, along with many other students were expelled from Sage Hall. Ben never got over Laura and eventually disappears from the preppie scene. Ellis, in a stroke of twisted, unjust luck, never had his “pre-ordained” path changed despite his deplorable actions. Toby says he knows he should feel guilty and bad and he does. However, he misses all the times he had, even with Ellis, the kid who sold him out. He misses the brief moment he had with Alex, and that’s all it would ever be; for he never saw Alex again after he was arrested.
As the credits roll, we are shown a brief clip of the real life 60 Minutes report of the incident the film was based on. Derek Oatis (who Tobias Hammel is based on) eventually pleaded guilty and was given mercy by the court. Derek was sentenced to five years probation, and 5000 hours of community service. He has since turned his life around and currently works as a lawyer.
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