1998 – Overnight Delivery

Paul as Wyatt Trips
Directed by: Jason Bloom
Written by: Kevin Smith
Produced by: Dan Etheridge, Brad Krevoy, Steven Stabler
Production year: 1997
Original release: April 7, 1998
Running time: 1 hour, 28 minutes
Other cast: Christine Taylor, Reese Witherspoon
Misc: IMDB | Amazon | iTunes

College student Wyatt (Paul Rudd) is convinced that his hometown girlfriend, Kimberly (Christine Taylor), is cheating on him. Disconsolate at a strip club, he nonetheless tries to defend the honor of Ivy (Reese Witherspoon), one of the dancers, who befriends him for his gesture. Ivy convinces Wyatt that he should send Kimberly a vicious breakup letter, which he does, by express mail. When he has second thoughts, he and Ivy hit the road to retrieve the note before it reaches its destination.