Watch Overnight Delivery

Overnight Delivery is a 1998 romantic comedy directed by Jason Bloom, starring Paul Rudd, Christine Taylor, Reese Witherspoon, and Sarah Silverman. The movie revolves around Wyatt Tripps (Paul Rudd), a college student who sends a nasty letter to his girlfriend, Kimberly Jasney (Christine Taylor), back home in Iowa after she breaks up with him. In a state of drunk distress, Wyatt vents his frustration entrusting a close friend to mail the letter for him, however, he later has a change of heart, believing that it was a mistake to write the letter in the first place, and decides to travel to Iowa to stop the letter from being delivered.

He enlists the assistance of a sassy and streetwise fellow student, Ivy Miller (Reese Witherspoon), to accompany him on his journey to Iowa. Along the way, the two confront several obstacles and get into some misadventures including an altercation with a truck driver, a robbery, getting stranded in a snowstorm, and being chased by the police. Ivy's devil-may-care attitude helps them navigate their way through the predicaments, though she eventually starts to fall for Wyatt along the way.

Meanwhile, Kimberly receives Wyatt's letter and is devastated by its contents which lead her to make a drastic decision that forces Wyatt and Ivy to race back to school before it's too late. Along the way, they discover more about each other, themselves, and the relationship they have established while on this impromptu trip. The tale ends with a plot twist that leaves the audience stunned.

The movie's plot has been compared to the iconic 1987 film, "The Sure Thing," starring John Cusack and Daphne Zuniga, but Overnight Delivery has a more modern and fresh approach to the storyline. The film is a mixture of comedy, romance, and road trip movie genres. The humor present throughout is relatable and well-acted, especially by Sarah Silverman, who plays Ivy's roommate. The witty one-liners and situational comedy provide excellent comic relief for the audience.

Paul Rudd's portrayal of Wyatt is charming and amusing, while Reese Witherspoon's portrayal of Ivy is spunky and unapologetic. The two have flawless chemistry and complement each other perfectly. The addition of Christine Taylor's character Kimberly adds tension and drama to the storyline, which provides a change of tone midway through the movie.

Overnight Delivery is not just a movie about a road trip and a boy chasing a girl, it defines love in an unconventional way. The film has showcased the turmoil someone goes through when they break up with their partner, the desperation one might feel when trying to mend their mistakes, and the unconditional connection that they might have with their closest friends. The movie raises some pertinent questions like when does one know it's too late to make amends; when does one give up on somebody they love or how far they can go to express their love for someone.

Overall, Overnight Delivery is an entertaining and gripping movie that leaves a lasting impression on the viewers. It is a unique blend of humor, romance, and drama that is enjoyable for everyone to watch. It is a perfect example of the romantic comedy genre of the 90s, and it will leave audiences laughing, rooting for the characters, and eagerly anticipating what is to come next.

Overnight Delivery is a 1996 comedy with a runtime of 1 hour and 27 minutes. It has received moderate reviews from critics and viewers, who have given it an IMDb score of 6.1.