Dirty Deeds 2005

On the Friday night of the high school’s homecoming weekend, the bold and impulsive Zach Harper [Milo Ventimiglia] throws himself into the infamous Dirty Deeds, a brutal list of ten challenges that must be completed between dusk and dawn. The urban legend around the list is clear: the last student to finish it, Duncan Rime [Charles Durning], did so back in 1989 when only eight tasks existed, and Rime later reveals that every time someone completes the entire sequence, new tasks are added to the tally. This twist fuels Zach’s resolve as he chases a sense of achievement that feels dangerously close to a win.

Zach’s motive is personal and charged with care for Meg Cummings [Lacey Chabert], a classmate who wants nothing more than to see her younger brother Kyle avoid trouble. Kyle’s desire to prove himself to the school’s jocks pushes him toward the challenge, a path Meg fears will only invite trouble. Meg’s protective instincts clash with Zach’s determination, and while she never intended for Zach to take on the deeds in place of her brother, he chooses to see the night through for them both.

The night unfolds with a mix of daring and deception. Zach begins by slipping a beer into a coffee cup and drinking it in front of the cops, a sly move meant to mask his real purpose while the authorities stand watch over those who chase the list. With each new task, the atmosphere grows tenser as the school’s toughest crowd, the jocks, do everything possible to stop him. Throughout the journey, Zach leans on people around him to pull off the more difficult challenges, and an unexpected encounter with Duncan Rime itself yields a stark warning: victory can feel hollow if it’s earned at others’ expense.

As the clock ticks, Zach confronts moments of doubt. He considers quitting, but interference from Dan and JD—the tough duo from Deed #2—threatens to derail his mission by trying to ruin the carnival and pin the blame on him. A last-minute lifeline comes from Vincent Scarno, the owner of the car used in Deed #8, whose aid helps Zach flip the situation just in time. The night’s chaos crescendos into a revelation about what the deed’s true price might be, and, in a surprising turn, Zach and Meg find common ground and grow closer as they reflect on the exhilaration and risk of the challenge, culminating in a shared bond that hints at something deeper beyond the thrill of the list.