National Lampoon’s The Legend of Awesomest Maximus

Awesomest, a not very bright general in Troy, is introduced along with his father-in-law King Looney and his right-hand man Quantus. The story highlights Awesomest's dissatisfaction with his marriage and his tendency to visit strip clubs for entertainment. Looney's family dynamics hint at political tensions over potential succession.

King Looney sends Awesomest on an important mission to help Orlando, his son, negotiate with the Greeks and avoid provoking a war. This is Awesomest's first solo assignment, and Hotessa, his wife, warns him not to mess up, as she aspires to become Queen.

The Greek king Erotic is depicted as a strange, sexually wild character, and his best warrior Testachillies is presented as an indestructible but vulnerable warrior due to his birth circumstances. Erotic insists on involving Testachillies in the conflict for glory, but Testachillies is reluctant, especially after consulting his mother Milfia.

Orlando, Loony's son, enjoys time with Ellen, Erotic's wife, and invites her to Troy, promising her a large trust fund and excitement over the impending war. Ellen is eager for the chaos and agrees to come with Orlando, leading to her refuge in Troy upon Loony's intervention.

Hotessa worries that Loony might crown Orlando as king and sends Awesomest to consult the F'Ers, diseased priests who indulge in perversions. The F'Ers tell Awesomest to choose a number and predict a battle involving 300 men, foreshadowing the Greek attack.

Testachillies, seeking to escape his overbearing mother Milfia who disapproves of his plans to fight in Troy, departs early with his cousin. His crew attempts to delay him, but they are all killed by arrows from the beach once he reaches Troy.

Testachillies refuses to fight initially due to poor accommodations. The treaty talks between Troy and the Greeks fail when Erotic attacks, and the 300 Spartans fight valiantly to push the Greek forces off the cliffs, causing chaos in Troy.

Loony gives Orlando the treasured sword of Troy, emphasizing its importance. Meanwhile, the Greek leader Erotic seduces Minorities with his tactics to breach Troy's defenses, expanding the chaos within the city.

Awesomest survives Troy's fall when he is captured and sold into slavery in a gladiator show. Under Erotic's orders, he's trained for the entertainment event, learning about his troubled past and proving his strength by killing Testachillies' cousin during the contest.

Testachillies arrives at the arena intending to kill Awesomest but finds him being tortured. He retreats to Troy. In the chaos, Erotic constructs a giant phallus with Greek soldiers inside, leading to the city's destruction as Greek forces emerge from it.

Awesomest challenges Erotic to a one-on-one duel, with Testachillies as a substitute. During the fight, Awesomest exploits Testachillies' vulnerability in his testicles, leading to Testachillies' fall and ultimately saving Troy.

With Testachillies defeated, Erotic and Orlando declare their love, ending hostilities. Ellen, revealing her sexuality, moves in with Hotessa and Awesomest, indicating a resolution of personal and political conflicts.