Overnight Delivery 1998
Directed by
Jason Bloom
Made by
New Line Cinema
Overnight Delivery Plot Summary
Read the complete plot summary and ending explained for Overnight Delivery (1998). From turning points to emotional moments, uncover what really happened and why it matters.
Wyatt Trips is a student at Twin Cities College in Minneapolis, Minnesota. He is in a long-distance relationship with his high school girlfriend, Kimberly Jasney, who is studying at the University of Memphis. Wyatt loves Kim, even though they have never consummated their love.
One day, after a phone call with Kim, a roommate’s remark leads him to believe Kim is cheating with some guy named “The Ricker.” Heartbroken, he goes to a strip club and meets a dancer, Ivy Miller, who suggests he break things off with Kim by sending a scathing letter and a topless photo of himself with Ivy. Wyatt follows the plan and sends the package through Global Express, hoping to sever the relationship for good.
The next morning, Kim calls Wyatt claiming “The Ricker” is a dog she had to dogsit. Regretting his rash action, he learns he has only 24 hours to intercept the package before it reaches her. Wyatt and Ivy head to the Global Express office, where they run into a spiteful classmate of Wyatt’s who refuses to help. Wyatt tries to persuade Hal Ipswich, the deliveryman, to hand over the package, but Hal worries Wyatt is a spy for the company and refuses to break the rules.
Wyatt buys a flight to Memphis, but his co-passenger turns out to be a serial killer, John Dwayne Beezly. Wyatt manages to escape and reunites with Ivy on the road. Fearing FBI scrutiny if he returns to the airport, he convinces Ivy to drive him all the way. They soon encounter the Global Express delivery truck at a gas station, and Wyatt breaks into the truck to locate the package, only for the vehicle to pull away again. Ivy gives chase, but they fail to retrieve the package.
At their next stop in Des Moines, Iowa, airport officials won’t let Wyatt board a connecting flight, so they press on toward St. Louis, Missouri. En route, an argument leads to an accident that sends their vehicle tumbling into a river. After a playful dinner at a cowboy diner, they are arrested for dodging the bill. After bail, they discover the delivery truck parked outside a diner. While Hal is dining, Wyatt tries to drain the truck’s gas to stall him, but a stray cigarette sets the fuel ablaze and the truck explodes. The truck rumbles away, undeterred, and Wyatt and Ivy steal a drunk’s car to press on toward Kim’s campus.
Wyatt finally says goodbye to Ivy and chases Hal to stop him, arriving just in time. Yet after meeting Kim, Wyatt realizes his true feelings lie with Ivy, not Kim. He breaks up with Kim and, moments later, spots another man wearing the same locket Kim once gave him, recognizing him as “The Ricker” and realizing Kim’s betrayal. He lets Hal complete the delivery and confesses his love for Ivy, who accepts his feelings with a kiss.
Overnight Delivery Timeline
Follow the complete movie timeline of Overnight Delivery (1998) with every major event in chronological order. Great for understanding complex plots and story progression.
Wyatt's relationship and distance
Wyatt Trips is a student in Minneapolis and is in a long-distance relationship with Kim Jasney, who is in Memphis. They have never consummated their love, which already creates tension. Wyatt worries about the state of their relationship as the story opens.
Suspicion of infidelity
Wyatt's phone call with Kim is interrupted by her roommate, who hints that Kim might be seeing someone else, the so-called 'The Ricker'. Wyatt's heart sinks as he misreads a situation as infidelity. He becomes convinced something is going wrong in his relationship.
Ivy the stripper offers a plan
Wyatt goes to a strip club and meets Ivy Miller, a dancer who becomes entangled with his plan. Ivy suggests sending Kim a harsh breakup letter along with a topless photo of Wyatt with Ivy. Wyatt reluctantly agrees and sets up an overnight delivery to Kim via Global Express.
Package sent by Global Express
Wyatt completes the plan and sends the scathing letter and the topless photo to Kim via Global Express, hoping to end the relationship quickly. The package is in transit, and Wyatt feels he has taken decisive action. Ivy agrees to help but remains uneasy about the consequences.
Kim reveals the truth and Wyatt's deadline
The next morning Kim calls, explaining that 'The Ricker' is actually a dog she had to dogsit, which undercuts Wyatt's assumption. Wyatt regrets his actions and discovers he has 24 hours to retrieve the package before it reaches Kim. He realizes the countdown has begun.
Global Express chase begins
Wyatt and Ivy go to the Global Express office to retrieve the package, where they meet Hal Ipswich, a stubborn deliveryman who refuses to break the rules. Wyatt tries to appeal to Hal, but the firm rule-bound employee won't cooperate. The encounter signals the start of a scavenger hunt for the valuable package.
Tangled escape and road alliance
Wyatt buys a ticket to Memphis, but his co-passenger turns out to be a serial killer who takes him hostage. Wyatt escapes and runs into Ivy on the road, who agrees to drive him toward Memphis to beat the deadline. They become reluctant allies in the cross-country chase.
Gas station truck encounter
Wyatt and Ivy locate the Global Express delivery truck at a gas station. Wyatt breaks inside to seize the package, but the truck drives away before they can grab it. Ivy gives chase, but they cannot retrieve the package before it disappears again.
Des Moines to St. Louis detour
Their journey continues to Des Moines and then St. Louis after an accidental detour. Airport officials refuse to let Wyatt board a connecting flight, forcing them to improvise. They share a diner moment where tensions rise as they travel through the Midwest.
Dramatic car crash and chase resurfaces
A river accident follows their argument as their rental car falls into a river, stranding them briefly. After posting bail for a run-in with the law, they spot the delivery truck again outside a diner, renewing the chase. The dramatic sequence raises the stakes for keeping the package safe.
Gas-tank sabotage and truck explosion
Wyatt empties the truck's gas tank to stall Hal, but a stray cigarette butt ignites the fumes and the truck explodes. Hal remains unshaken and continues delivering the package, proving just how relentless he is. Wyatt and Ivy are left to improvise once more.
Campus chase concludes
Wyatt and Ivy steal a drunk's car and drive to Kim's campus for a final confrontation. Wyatt chases Hal to stop him and arrives just as he reaches Kim. His feelings for Ivy begin to crystallize during this tense moment.
Truth surfaces and love shifts
Wyatt realizes he loves Ivy after meeting Kim and re-evaluating his feelings. He breaks up with Kim and seemingly accepts his new love. In a twist, he encounters another guy wearing Kim's locket who is revealed as 'The Ricker' and confirms Kim's infidelity.
Resolution and new romance
Wyatt allows Hal to deliver the package, choosing honesty and commitment with Ivy. He confesses his love to Ivy, who responds with a passionate kiss, sealing the new relationship. The package is delivered, and Wyatt has chosen his future with Ivy.
Overnight Delivery Characters
Explore all characters from Overnight Delivery (1998). Get detailed profiles with their roles, arcs, and key relationships explained.
Wyatt Trips (Paul Rudd)
Wyatt Trips is a Twin Cities College student whose long-distance relationship with Kim triggers a desperate, impulsive pursuit. After believing Kim is cheating, he sends a dramatic letter and a photo with Ivy, launching a chaotic chase for the overnight package. The journey forces him to confront his true priorities and, by the end, realize his love for Ivy.
Ivy Miller (Reese Witherspoon)
Ivy Miller is a stripper Wyatt meets at a club after a night of drinking. She suggests a provocative way to break up, and then joins in the pursuit to retrieve the package. Through the road-tripping chaos, she becomes a catalyst for Wyatt's emotional awakening and a potential romance.
Kimberly Jasney (Christine Taylor)
Kim Jasney is Wyatt's long-distance girlfriend, a student at the University of Memphis. She becomes the target of the misunderstanding about 'The Ricker', and the package Wyatt sends is meant for her. Her role is mainly as a catalyst for Wyatt's actions, and the ending reveals the truth about her relationship.
Hal Ipswich (Larry Drake)
Hal Ipswich is the deliveryman for Global Express who refuses to break the rules and suspects Wyatt of espionage. His stubborn adherence to protocol drives much of the obstacle-filled chase. The dynamics create tension and comic interplay in the pursuit.
The 'Ricker' (Matt Klemp)
The Ricker is the mysterious figure Wyatt believes is his girlfriend's other lover. The character's true identity ties to the locket clue, and the pursuit revolves around uncovering who this figure really is.
John Dwayne Beezly (Tobin Bell)
John Dwayne Beezly is a serial killer Wyatt encounters as a flight passenger who takes him hostage. Wyatt somehow escapes and continues the chase, adding danger to the journey and escalating the stakes.
Overnight Delivery Settings
Learn where and when Overnight Delivery (1998) takes place. Explore the film’s settings, era, and how they shape the narrative.
Time period
late 1990s
The events take place in a late 1990s setting, a time when long-distance relationships relied on phone calls, letters, and road trips. The backdrop features roadside diners, airports, and early digital communication, shaping the pace of Wyatt and Ivy's pursuit. The era's limitations drive the tension and humor of the chase.
Location
Minneapolis, Minnesota, Memphis, Tennessee, Des Moines, Iowa, St. Louis, Missouri
The story moves from a campus setting in Minneapolis through a cross-country chase that hits several midwestern and southern cities. It centers on a college student navigating a chaotic, relationship-driven crisis while using a delivery service as the conduit for the plot. The setting blends urban spaces with highway towns, framing the road movie atmosphere.
Overnight Delivery Themes
Discover the main themes in Overnight Delivery (1998). Analyze the deeper meanings, emotional layers, and social commentary behind the film.
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Romance
Wyatt's heartbreak launches a journey that tests loyalty and honesty. He evolves from seeking revenge to recognizing genuine feelings for Ivy, showing how love can blossom from chaotic misreads. The road trip becomes a catalyst for emotional growth and a real connection.
🔎
Trust and Deception
Miscommunication drives the plot as suspicions of infidelity ignite a reckless quest. The pursuit rests on misreads and secrets, forcing characters to confront what they truly value. Truths eventually unfold, reshaping relationships.
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Road Trip
The film unfolds as a travel-turned-morality tale, using a cross-country chase to explore character choices. Each stop exposes flaws and strengths, turning a delivery into a journey of self-discovery. The road becomes a playground for comedy, danger, and romance.
Overnight Delivery Spoiler-Free Summary
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In the bustling corridors of a Midwestern college, Wyatt Trips finds his world upended by a sudden bout of jealousy that sends him careening toward a rash decision. His long‑distance romance with Kimberly Jasney, a fellow student half a thousand miles away, has always been a quiet, hopeful connection, yet a misinterpreted conversation ignites a frantic need to act before the moment slips away.
The film unfolds against a backdrop of relentless motion—a ticking twenty‑four‑hour countdown that transforms ordinary errands into a high‑stakes race. The tone is a lively blend of comedy and suspense, where the absurdity of a misplaced letter collides with the urgency of a courier who will stop at nothing to see his parcel delivered. The cityscapes of Minneapolis, the open road, and a series of quirky pit stops create a kinetic rhythm that keeps the audience’s pulse in step with the chase.
Enter Ivy Miller, a magnetic presence who offers a daring alternative to Wyatt’s turmoil, and Hal Ipswich, the stoic deliveryman whose single‑minded dedication adds a formidable shadow to the pursuit. Their interactions spark a volatile mix of attraction, friction, and unexpected camaraderie, turning a simple miscommunication into a journey of self‑discovery. Wyatt’s impulsive nature clashes and harmonizes with Ivy’s bold confidence, while Hal’s unflinching focus serves as both obstacle and catalyst.
As the deadline looms, Overnight Delivery paints a portrait of youthful desperation, humor, and the frantic search for clarity when emotions run wild. The story promises a whirlwind ride through mistaken assumptions, relentless pursuit, and the possibility that love might be found in the most unlikely of companions, all while the clock keeps ticking toward an uncertain but electrifying climax.
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