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Overnight Delivery

Release: 1998
Genres: Comedy, Romance
Summary: Wyatt writes an angry letter to his girlfriend, believing she’s dating Ricker. Ricker’s a dog. Helped by stripper Ivy, he tries to get the letter off a truck the next 24 hours.
Rating: PG-13
Runtime: 1h 27m

Overnight Delivery

Nov 11, 2023

For many people, this is a favorite sick-day movie. An underrated and forgotten gem of a romantic comedy starring a very youthful Paul Rudd (his second movie after Clueless, and his first as lead) and Reese Witherspoon (the same year she was in Pleasantville, maybe her most breakout role). It is wacky, it has some charm, but ultimately, for my taste, I don’t think it is a very good movie.

Overnight Delivery is part of a reasonably small sub-genre that mixes two classics of Americana in film: the road trip and the romantic comedy. The concept of mixing travel and romance is nothing unique in world cinema, but America’s deeply rooted love of cars and lack of alternatives like an efficient and modern rail network, as well as the nostalgic mystique of roadside attraction speckled transit corridors like Route 66, make this kind of movie an essentially singularly American twist on the romantic comedy. It is found in films such as It Happened One Night, the first third of When Harry Met Sally (with a twist), in the oft overlooked John Cusack vehicle The Sure Thing, among others.

For direct comparison, the Overnight Delivery calls to mind two films: Road Trip and the aforementioned The Sure Thing. All three involve college students making a trip across a large chunk of the country and, during that journey, finding a fresh perspective on love. Tonally, Overnight Delivery sits in between the two. Road Trip is more a 2000s era sex comedy than a romcom and The Sure Thing, while not authored by John Hughes, shares in his 80s early adult sincerity. Overnight Delivery is zanier than the later but more subdued than the former.

Road Trip and Overnight Delivery’s plots are eerily similar, with Overnight Delivery preceding Road Trip by a few years. They both have leads with high school sweethearts that are attending a different school, fears over infidelity leading to rash decisions, a road trip structured around preventing a package from reaching its destination (said high school sweetheart), and a journey that serves up wacky, barely believable hijinx along the way. Despite that, while watching I found myself much more comparing Overnight Delivery to The Sure Thing.

Road Trip only really uses its plot to set up raunchy gags and ridiculous situations. The Sure Thing, on the other hand, is a film with a big heart where the romance takes center stage. The Sure Thing, like Overnight Delivery, has two characters who are not supposed to be falling in love fall in love over the course of the journey, despite prior entanglements. The Sure Thing is also, unluckily for Overnight Delivery, a much better movie.

Overnight Delivery, despite its fun premise, never really figures out how to walk that line between the heart and humanity of the two people falling for one another, something that usually requires a certain degree of groundedness, and its desire to punctuate the film with all the zany moments the scriptwriters thought would be funny. The closest they come to getting this right are the numerous interactions with the delivery driver and his truck which, thanks to their immediate pertinence to the plot and grounded absurdity, feel natural in a way. The furthest is when the main character ends up sitting next to a serial killer on a plane flight, leading to them fleeing FBI custody because staying around to be questioned would allow the doomed package to arrive un-intercepted. This unevenness of tone and resulting difficulty keeping up the suspension of disbelief creates something that, despite its best efforts, lands only a few charming moments while feeling relatively charmless the rest of the time.

This disconnected tone and lack of grounded believability is, unfortunately, also true in the performances. While he became a much better actor later in life, this film really shows Paul Rudd’s immaturity as a performer early in his career. The charisma and chemistry of its central duo never fully seems to click or have time within the narrative to gel the way you might want. Both characters, for different reasons, struggle to come across as likable, but Paul Rudd’s more so. Scenes always feel a little pushed, like borderline Disney Channel acting pushed, which is most noticeable in Paul Rudd’s performance. There is a pair of scenes in the beginning where he goes with some friends to get drunk at a dance club that are just…not good, and it very much sets the tone for the rest of the flick.

In the end, the main feeling I get from Overnight Delivery is a film that just missed the mark. It has a fun premise, a cast with a lot of (perhaps yet unrealized) potential, and there are moments that shine that give you a glimpse at what could have been. Unfortunately, those moments are few and far between and what remains is something that feels a bit like a 90s rip off of a much better 80s film with the same core DNA.

Would Recommend: If you love a good road trip romance.

Would Not Recommend: If you are hoping for a romantic comedy where the romance is put first.