National Lampoon’s The Legend of Awesomest Maximus

Awesomest, a rather dim-witted general in the city of Troy, Will Sasso, finds himself embroiled in a series of bizarre and humorous events that threaten to change the fate of Troy forever. His father-in-law, Rip Torn, plays the comically eccentric King Looney, who is secretly conflicted about his heir, Orlando, the king's gay son, played by Gary Lundy. Awesomest’s loyal right-hand man, Quantus, constantly wins battles for him and keeps him alive, but Awesomest’s personal life is fraught with dissatisfaction, leading him to frequent strip clubs seeking entertainment.

Hotessa, played by Kristanna Loken, is Awesomest's wife and the princess of Troy. She harbors worries that her father might choose Orlando to be the next ruler of Troy, an idea that causes her significant anxiety. In an effort to prevent war and keep Orlando safe, King Looney sends Awesomest on a diplomatic mission to the Greeks—an unprecedented task for him, as it’s his first solo assignment of such importance. Hotessa warns him not to mess up, as she aspires to become Queen herself.

The Greek King Erotic, portrayed by Khary Payton, is a peculiar character with a bizarre obsession with sex, making him quite a controversial and unsettling figure. His top warrior, Testachillies, played by Ian Ziering, is a cocky and irritating man who believes himself to be indestructible thanks to a legendary origin involving a goddess dipping him into a magical river—but with an unfortunate vulnerability in his testicles, born from his mother's carelessness.

Orlando is enjoying himself in Troy, particularly with Ellen, played by Sophie Monk, who is Erotic’s wife. Orlando, eager for adventure and motivated by his sizable trust fund, invites Ellen to accompany him to Troy, promising her excitement over the possibility of a future war that would give her a story to tell. Ellen agrees, and Awesomest, ever eager to please, agrees to escort her, especially after she exposes her breast to him.

King Looney, pleased that Orlando isn't a fairy, grants refuge to Ellen, while Erotic's ambitions grow—he desires to fight in the war to gain glory, especially through his warrior, Testachillies. Testy, as he’s called, seeks his mother Milfia’s approval to leave for Troy, but she warns him of imminent death if he goes. Despite her warnings, Testachillies chooses to leave to escape her suffocating clutches.

Meanwhile, Hotessa fears that Looney might declare Orlando the next king, prompting her to send Awesomest to the F’Ers, a group of diseased priests eager to exploit their supposed divine powers. The F’Ers, high on drugs and perversion, tell Awesomest to pick a number—he chooses 300—and that he must fight with 300 men, throwing him into a whirlwind of chaos and comic mishaps.

In Troy, Testachillies is eager to prove himself but is hindered by poor equipment supplied by Erotic. During the treaty negotiations, Erotic takes a liking to Orlando's wife Ellen, complicating diplomatic efforts. The talks falter, and Erotic retaliates with an attack. The iconic fight ensues, with the famed 300 troops bravely repelling the Greek invaders, pushing them off the cliffs, as Awesomest falls during the chaos, much to the relief of Quantus.

King Looney bestows Orlando with the legendary sword of Troy, entrusting him with its safety. Ellen, embracing her liberated identity, gives Hotessa a dildo in a humorous gesture, while Erotic cunningly seduces Minorities, a dwarf played by Tony Cox, with nudity and allure to facilitate a covert escape over Troy's walls.

Surviving the initial battle, Awesomest is captured and sold into slavery, forced to participate in a gladiator event. Under the ownership of a brutal event organizer, who has a contract with Erotic, Awesomest undergoes rigorous training. Among the revelations he uncovers about his own past, he learns that his father once discarded him in a thunderstorm to adopt the child of his maid, shaping his sense of identity.

In the arena, Awesomest proves his mettle by defeating Testachillies’s cousin, who arrives to challenge him, culminating in a brutal fight where Awesomest exploits Testachillies’s weakness in his balls—delivering the decisive blow and bringing the Greek warrior’s reign of arrogance to an end. This act ultimately helps save Troy from destruction.

As the Greeks retreat, inspired by the absurdity and heroism of the battles, Erotic is defeated, and he and Orlando declare their love for each other, ending the war in an unconventional but humorous resolution. Ellen, embracing her sexuality and independence, moves in with Hotessa and Awesomest, celebrating their bizarre yet victorious life together.

Throughout all the chaos, the movie delivers a satire-filled parody of classic war stories, filled with absurd characters, exaggerated action, and comedic moments that challenge traditional hero tropes with vulgar humor and over-the-top antics.