The film gained some recognition due to James Rolfe slyly promoting the film in a top 10 video he produced the same year the film was released. This is due to his friendship with von Manahan, the filmmaker.
At the dawn of his quarter-life crisis, Caleb Callahan (Jeremy Luno) returns home to Bucks County after recently dropping out of college. Upon his return, he discovers a note from his lifelong friends Montag (Michael Hampton) and Swank (Nikitas Manikatos) to meet and catch up on old times. Montag, an eccentric man-child and serial prankster, requests that Caleb joins him and Swank on one of his many schemes. After seeing his old bandana mask from his pranking days with the two, Caleb agrees to join them.
Caleb, dressed in cape and mask, distracts the Washington Elementary School’s noon aids and causes bedlam among the students with a soapbox speech on recess grounds. Meanwhile, Montag and Swank discover a map that leads to an old time capsule after randomly searching the principal’s office. Caleb (having escaped from the noon aids’ clutches), return inside the school to return an old overdue library book, When the Leaves Fall. He hears music, following it to the school’s music room to find Cole (Mackenzie Firgens) playing piano, he’s speechless by her presence. The trio are immediately confronted by Cole’s father, the principal of the Washington Elementary, but they escape his clutches and their scheme a success. Later that night at Sherrwood Tavern, Caleb and Swank go out for drinks and darts. Caleb, an avid darts player, shows Swank how to play, only to be disrupted by Officer Scar (Jeff Berg), Caleb’s old arch nemesis. Scar, the dart champion of Sherrwood, prevents them from further playing, who nightly guards the area by the dartboard to prevent possible rivals at the game. As they leave, Caleb runs into Cole, who runs a nighttime taxi service to prevent drunks from roaming the streets. Cole playfully informs Caleb that she has his book (left behind after his confrontation with her father), and Caleb responds by saying he’ll call her tomorrow.
While Montag discusses his next scheme with Caleb and Swank at the park, Montag gets into a fight with his long-time rival, the obnoxious Tanner (Billy Tanner) after being loudly insulted by him. Meanwhile, Caleb sees James Paddington (Paul Gleason), the county’s gubernatorial candidate, discussing to a crowd of potential voters the history of the Revolutionary War and the town’s history behind it. Caleb argues with Paddington that Washington’s attack on the British was considered cheating for fighting on Christmas. After Paddington publicly berates Montag and Swank before the crowd, Caleb says out of all the pranks Montag has done in the past, their upcoming scheme against Paddington is the one he can truly agree on.
At 2:00 a.m., Montag and Swank hide on a stakeout by Caleb’s house where they are interrogated by Scar. Scar informs Montag that he knows that he was behind the trespassing at Washington Elementary, and warns that the next scheme they concoct, he will intervene. Caleb and Cole begin seeing each other more and more and eventually become lovers, much to Montag’s annoyance. Caleb introduces Cole to Montag and Swank so they can get to know her, but Scar intervenes, revealing to Caleb that he had a relationship with Cole before him, reveling in Caleb’s anger at this revelation.
Caleb, Cole and the others return to Sherrwood Tavern for drinks and darts where they again run into Scar, who prevents them from further playing. Cole insults Scar by proclaiming that Caleb will take his dart champion title from him. They play a single match, with Scar being victorious. When Cole asks Caleb about his history with Scar and of the diamond shaped scar on his cheek, Caleb refuses to answer, considering the inquiry to be rude. As Caleb leaves for the restroom, Swank reveals to Cole their history with Scar dating back from high school. Montag challenged Scar and his crew to a basketball match, only to lose miserably. As Scar reveled in his victory, Montag shoved Scar, only to receive a beating in retaliation. Caleb defends Montag by throwing a garbage can at Scar, the impact pushed Scar's face against a wire fence and ripped a bloody diamond shaped mark into his left cheek. Humiliated, Scar swears vengeance against Caleb and his friends and disappears.
Wintertime, Caleb and Cole meets up with Montag at the site of Paddington Brothers Construction, where Montag plans on leaving upper deckers in every master bathroom on the block. Caleb refuses to go along with the scheme and leaves with Cole. Cole confronts Caleb, who plans on ducking out of a date to join Montag and Swank with Operation: Sorbet, a scheme where they dig up their old elementary school’s time capsule and replace the capsule's contents with pornography. Caleb explains that he tries to keep a balance between his relationship with Cole and his friendship with Montag, but Cole explains that it’s not good enough and gives Caleb an ultimatum: either not follow through with Montag’s ongoing schemes or their relationship ends. Caleb backs out of Operation: Sorbet, and Montag is forced to hire the inexperienced Simon (Brett Jacobsen) to proceed with the prank. Scar foils Montag’s plans (while Tanner further humiliates Montag and Swank with water balloons) and beats him mercilessly. Operation: Sorbet ends in failure.
Caleb later meets up with Montag at his current residence (their childhood tree house) finding him defeated and demoralized by Operation: Sorbet’s failure. Caleb apologies for bailing out of him and proclaims his full involvement with Montag’s next upcoming scheme. Montag, Caleb and Swank plan on sabotaging Paddington’s annual reenactment of Washington Crossing of the Delaware as Native Americans. The trio attack Paddington’s crew with jousting cardboard tubes, while Montag swipes Paddington’s costume wig of George Washington, claiming it as his prize. Montag trips as he tries to escape, falling victim to Paddington’s impending attack with a replica saber. Caleb quickly disables Paddington with a throwing dart before he can attack Montag and falls in the icy Delaware.
The next day after their victory celebration, Caleb discovers that a bounty has been placed on him after a picture of him (in disguise) is shown disarming Paddington. Caleb is distraught, but Montag reassures him that his identity will remain safe. Meanwhile, Scar, who still harbors feelings for Cole, deliberately gets drunk at Sherrwood Tavern and calls her for a ride home. During the ride, Scar reveals to Cole photographic evidence of Caleb’s involvement in the Reenactment sabotage, where he will reveal them to the authorities unless Cole has sex with him. Cole and Scar engage in the act in her car, and Cole becomes in sole possession of the photos, proclaiming to Scar that she’s doing this because she loves Caleb. Montag runs into Cole while she tears up in her car, revealing that he knows about the affair.
Later at Sherrwood Tavern, Paddington, having recovered from his injuries, announces the tavern’s annual dart championship tournament, where the winner of the tournament gets a prize pack, including debt-free rights from the tavern. Paddington believes that the dart thrower who injured him will attend the tournament, and he will be able to catch him and arrest him for the assault during the Reenactment. Scar thanks Cole for the ride home from the tavern earlier and requests another ride. Through heavy implication, Scar reveals to Caleb of Cole having sex with him. Caleb is angry at Cole’s actions, but understands the reasons behind it.
Caleb later visits Montag, who is busy cleaning up his tree house after it burned down sometime earlier from an accidental electrical fire. Caleb asks Montag for advice on how to get back at Scar, Montag answers by beating him at the dart tournament. He goads Caleb into regaining his confidence in his dart throwing ability and Caleb enters the tournament in disguise. Caleb and Scar make it to the finals, where Caleb narrowly beats Scar and claims the title of champion. His throwing darts match the same one used by during the Reenactment, and Caleb is promptly arrested by Paddington. However, Montag exonerates Caleb with a signed confession of his involvement of the scheme and delivers Paddington the wig stolen from him, claiming that Paddington doesn’t have enough valid evidence to lock Caleb away. Enraged, Scar attacks Caleb with a pool cue, but Montag defends him with his own pool cue, claiming that Scar’s anger has always been towards him, not Caleb. Scar overpowers Montag, and before he delivers the final blow, Swank hits from behind with a pool cue of his own, giving him a second scar and knocking him unconscious.
Springtime, Montag visits Caleb at Sherrwood Tavern, where he reveals that he’s chosen self-exile from Bucks County over jail time thanks to an old county law. Montag plans on returning to Bucks County one day by running for county commissioner, despite his lack of political experience. He says his goodbyes and Caleb takes over Montag’s role as serial prankster of Bucks County.Jeremy Luno as Caleb Callahan: The titular character, Caleb is a neutral, easygoing college-dropout who tries to appease everyone around him. Longtime friends of Montag and Swank, their schemes and pranks has inevitably pushed Caleb away from them and off to college, but eventually he made his way back to them.
Michael Hampton as L.R. Montag: A serial prankster, Montag's secret to life is the accomplishment of many short-term goals. Often unpredictable with radical personality swings, Caleb's justification for his friendship with Montag has been for him being "the most persistent son of a bitch" he's ever known.
Nikitas Manikatos as Swank: A sidekick of Montag's many schemes, he accompanies Montag's pranks for the sake of curiosity rather than that of loyalty, belief or trust.
Mackenzie Firgens as Cole: Caleb's girlfriend. She is often dumbfounded by Caleb's commitment to his friendship with Montag despite his erratic behavior. She is proficient in playing the piano and runs a nighttime taxi service for Sherrwood Tavern.
Billy Tanner as Tanner: A fellow prankster, Tanner has an antagonistic relationship with Montag, resulting in brawls, prank wars, and unpredictable verbals attacks of “Goddamn you, Montag!” His trademark standpoint is his “Tanner Dance”, which involves quick jarring motions of the neck and arms as Ween's "Where'd the Cheese Go?" plays in the background.
Jeff Berg as Jim "Officer Scar": Egotistical, violent, overly-dramatic, this self-appointed officer of the law has a constant, antagonistic relationship with Caleb and anyone associated with him. Scar is an exceptional darts player and former lover of Caleb's current girlfriend, Cole.
Brett Jacobsen as Simon: Hired to be Caleb's replacement for Operation: Sorbet, his sole qualification was he could fit into Caleb's mask and cape costume. He is shunned by Montag after being halted by Scar, despite Simon's determination to resume being a co-conspirator in Montag's upcoming schemes.
Paul Gleason as James Paddington: Real estate mogul and gubernatorial candidate of Bucks County, Paddington is an avid historian of George Washington. Self righteous, he diverts his wrath towards Caleb and his co-conspirators after getting injured and frozen after his sabotaged reenactment of Washington crossing the Delaware.