The movie starts with the shot of a truck backing up. This truck, along with about a dozen others are literally packed with shoes with the tag of "Recalled" all over them. We then cut to a helicopter with Drew Baylor (Orlando Bloom) riding in it. In his mind, Drew is discussing the difference between failure, which is the absence of success, and complete debacle, which is where people look at you and can't help but feel happy because the situation did not happen to them. The helicopter takes him to a big office building where EVERYONE he walks past gives him a look that screams "that poor bastard". He simply replies to each look with "I'm fine". As he walks down the hallway, a girl steps out of the office and is shocked to see him there. It is Ellen, Drew's girlfriend. She offers to drive him to Phil. When Drew sees Ellen, we hear him describe that very recently, he has decided to start collecting last looks, the looks you receive from someone when they believe they will never see you again (important throughout film). As they drive, Drew describes the prestige of the shoe company he works for, and showing that they were encouraged to be creative in their job. Their owner, Phil, is displayed in an iconic light and seems to be Drew's mentor. Drew mentions that people that are taken to see Phil are usually up for promotion...or otherwise. Drew recalls the steps that led him here, showing him designing a show that takes influence from sting rays, sacrificing Christmas with his tight knit family to prepare the release of the shoe, and hooking up with Ellen as he parties at the shoe release party. As things reach the peak of enjoyability, reality comes crashing back to Drew as Ellen stops their cart outside Phil's office.
Inside, Phil describes how unsure he is of how to handle failure. Drew's shoe will cost the company 970 million dollars of loss. Phil and Drew take a walk as Phil points out what he will have to cut to save the company, including the Environmental Big Brother department, making Drew literally responsible for environmental pollution (or so it is implied). Phil then recounts a memo he received which said that Drew's shoe make actually cause this generation to rescind back to bare feet, then bursts out laughing at the absurdity of the memo. Drew asks if there is anything he can do and Phil asks him to stand up for his work to a reporter downstairs. This essentially signals Drew's firing from the company and, once the report is published, downfall in the shoe industry.
Drew comes home to his apartment, exclaiming "Home Sweet Home". He then immediately goes to his knife cabinet and picks out the butcher knife. He then proceeds to empty out his apartment of all the gadgets, TVs, computers, etc, and builds his own "suicide machine" out of the knife, a mechanized exercise bike, and a remote control. Once he activated the switch, the bike's handle bars will jerk forward, while the seat jerks up, and the knife is duct-taped onto the handle bars. Drew is just about to push the button when his cell phone starts ringing. He answers it cordially and it's his sister, Heather (Judy Greer) with bad news. Drew tries to get her off the phone so he can commence his "deadly workout", but the sister finally blurts out that his father died, and she needs him to go retrieve his body so she can take care of their mother Hollie (Susan Sarandon, who is fantastic), who is completely in hysterics. Drew agrees to this, but secretly has the plan that he will take care of this, and then get back on the bike and complete his suicide.
Drew must take a red-eye flight to Kentucky, where his father was visiting his family. Apparently, his family never liked Hollie, who was viewed as the "Californian" who stole the father, Mitch, away from them. On the plane, Drew is ready to drift in his melancholy, but a stewardess named Claire (Kirsten Dunst) strikes up conversation with him. She offers to upgrade him to first class, since there are no other coach passengers, to which Drew finally relents. She then keeps up a conversation with him about names, since she describes herself as a student of names. They talk about Drew's dad, though Drew does not mention his father's death, and Claire says Mitch's always seem like fun guys. Then they talk about Drew's ex-girlfriend Ellen, to which Claire recounts she's never known a good Ellen. When Drew tells her he's going to Elizabethtown, Claire draws him a map of streets to take, and she tells him to make sure he doesn't miss Exit 60B (important later). Later in the morning, she wakes Drew up when the plane lands in Kentucky. She gives him a set of wings and a coupon, saying he was their 10 millionth flier. As Drew starts to walk away in the terminal, Claire comes running out and screams at him to make sure he doesn't miss 60B a few times. She also yells to have a good time with Mitch. She lingers as he leaves.
Drew gets in his rental car to drive to Elizabethtown, and notices on the back of the coupon he got are Claire's home and cell numbers, and the number for the Auto Club "in case you get lost". As Drew drives along, we see a lot of Kentucky scenery interspersed with Drew looking for 60B. We then see an Indiana sign, and suddenly Drew is parked on a dirt road. He starts smacking the horn screaming "Did I pass a 60B? DID I MISS 60B????" He gets back on the road and shortly later, finds the exit for Elizabethtown (which is not 60B). As he drives through town, his dad's presence is evident, as there are lots of signs in remembrance of him, and the townspeople literally line the street welcoming Drew. Drew pulls into the funeral home and meets his cousin Jessie (Paul Schneider). Jessie escorts him back to the graveyard, where Jessie's father and Drew's uncle, Dale (Loudon Wainwright) stands with the funeral director Charles Dean. They tell drew they've kept the family plot reserved for Mitch, and Drew replies they are still unsure of their plans for the body, going between burying him and cremating, which everyone in town seems to be against.
Drew and the other men go to his Aunt Dora's house, which is basically a HUGE party with everyone in Drew's family praising him for his success in the shoe business (which is ironic to Drew considering he's about to become a failure in that). His Aunt shows him her picture room, which has pictures of everyone in the family. Then she suddenly stops and says "Except your mother...don't know why I never put a picture of her in here...". She lets Drew look at the pictures alone and he flashes back to memories of his younger self with his father and we can see they were close. As the party goes on, we see Jessie's son Samson, who is about 5 or 6, is a bit unruly and Jessie does nothing to correct this. This culminates when Drew goes outside and sees Samson backing a car out of the driveway! Drew runs and catches the car in time to stop him from doing damage and lots of the elders of the family somewhat scold him inside (but not Jessie, his father). A man walks in and the entire house goes silent. The man starts yelling about how they decided not to invite him. He then breaks out laughing and everyone joins in. His name is Bill Banyon (Bruce McGill). Later that night, we see Uncle Dale reprimanding Jessie, saying he needs to set rules for his son. Jessie tells his father he understands what he's saying, but Jessie is trying to be a non-conventionalist and try a different approach to raising his son. Uncle Dale then delivers the crushing line "You can't be a buddy to your son", which Drew somewhat ponders. Drew walks home with Jessie and Samson, where Jessie relates how his band opened for Lynyrd Skynard. That is, they were scheduled to play on a side stage on a different day of a festival that two surviving members of the band were playing at (did you get all that?). But they never played it, and they haven't played since. Drew takes amusement in this and then in Jessie's singing.
Drew goes to check in to a hotel, which has practically been wholly booked out to the wedding of Chuck and Cindy. Drew takes the last room, charging it on his company card. When he gets up to the room, he tries to call his sister, then his mother, then Ellen, each one not answering. Drew is very lonely and suddenly decides to call Claire. He leaves a rambling message and doesn't even really say why he's calling, just hangs up. Shortly after, his sister calls him, distraught because their mom has seemingly gone crazy. She's decided to learn how to cook organically in the wake of the father's death. Drew says he should be home soon, but then he gets a beep and tells Heather to hold on. The other call is Claire, who is glad to hear from Drew. She starts talking about things as Drew is trying to get her to hold. He finally gets her to hold while he gets back to Heather, who is still frantic about the mother. In the middle of all this, Ellen calls back too, trying to tell Drew goodbye (meaning she is leaving him). This results in a pretty funny scene where Drew is switching between 3 calls all together. After he gets Heather and Ellen off the phone, he calls Claire back just as she is getting home.
They end up having a long phone conversation about everything and nothing while they do routine things like laundry, changing a cat litter box and Drew relieving himself (and he holds the phone outside the bathroom when he flushes). Eventually, Drew sneaks out of his room and discovers the wedding party has left a room open with a bathtub full of beer bottles. Drew starts telling Claire he is stealing the wedding party's beer when he comes face to face with Chuck (Jed Rees). Chuck asks who Drew is and Drew explains he's there for his dad's funeral. Suddenly Chuck starts bawling and hugging Drew and telling him he's there for him, anything he needs. Drew is a little freaked out by this, but he seems to get along with Chuck and Chuck lets him keep the beer. Claire and Drew keep talking right up until around 4 or 5 in the morning. Claire happens to mention something about maybe it's better for them to be on the phone and Drew jokingly agrees. Eventually, they're both about ready to go to sleep. Both click their lights off at the same time, while still on the phone. Suddenly, Claire asks Drew if he'd like to meet somewhere between them and watch the sunrise, since he's only 45 minutes away. Drew says nothing at first but clicks his light back on, and then agrees. So they both stay on the phone and drive towards a mid point. They finally meet and hang up. They sit on a stone wall overlooking a lake for a moment, and then Claire says "Yeah, I think we peaked on the phone", to which Drew goes "Yeah, let's go" and they leave. There's a great shot where Drew and Claire's roads diverge, and there's a stoplight there. Claire says she's going to Hawaii (as a stewardess on a flight) and Drew asks her to call when she gets back. They then both say Aloha to each other and drive off.
As Drew drives back into town, he goes on more about this last looks thing as he looks around the town at memorials of his father. When he gets back into town, there is more discussion about burial or cremation and it's obvious that the family back home, "The Californians" as the Elizabeth townsfolk call them even though they live in Oregon, want cremation. Drew mentions Bill Banyon to his mother on the phone and she flies into a rage. She says that Bill Banyon conned Mitch out of lots of money years ago and that he should even be trying to attend the memorial is an outrage.
Later Drew is walking back into his hotel, very tired, when Claire calls him from another hotel, looking quite similar...She says something about checking out a pretty cute guy, which Drew gets kind of irritated about and says why are you telling me this when all of the sudden a balloon pops loudly. Drew stops and turns around to see what happened, when suddenly Claire sneaks up behind him and covers his eyes. Drew is amazed Claire is there and before he can ask about Hawaii, she takes him urn shopping. After picking out an urn and having a wonderful day out, Claire explains why she talked to Drew in the first place. She says the are both "substitute people" that do best on their own, or being partner to someone who is usually not around, as in the case of her boyfriend Bob. When they go to part, Drew and Claire nearly kiss, but don't, and Claire comments how she's glad she didn't, that way they still have a chance at being friends. She then says she has a personal interview tomorrow and if she fails, she gets transferred, which would kill Bob. So they part, again, but not before Claire gives Drew a videotape, saying "Play this for the (either last or loudest, couldn't make it out) kid in the world".
The next day, the Elizabethtown family is discussing burial arrangements and the memorial, and the family keeps pressing for burial. Finally, Drew erupts and says that he is being cremated because it is his mother's wishes and because she is only doing what Mitch wanted and they're not really from California, they are from Oregon, so you should just listen to the Californians advice. Drew suddenly realizes his Californian slip and starts laughing, to which everyone else joins in and everything's ok. Then, Drew goes into where Samson and a bunch of kids are being loud and unruly and sits Samson down and asks him to watch this with him. He then puts in the tape, which is of a burly man in a pickup truck. The man says he built this house behind him, but now termites have eaten it all up. So now he's going to blow it up! But he asks the kids to be quiet and promise to listen to their parents before he will. All the kids look up and go "yeah, listen to our parents. blow it up!". Then the guy says "Okay then, let's LIGHT THIS PUPPY" and proceeds to blow up the house in a very extreme fashion. Jessie sits and watches with his son, and we see Uncle Dale look on in astonishment. Later, Dale thanks Drew for taking an interest in Jessie and Samson. They stand around in the kitchen while Aunt Nora has the stove on, and Drew concentrates on the flame. Suddenly, we see him bolt to the crematorium, pounding on the door to stop the cremation. But it's already done, and the man gives Drew the ashes.
Drew goes back to the hotel, where he sees Claire partying with the wedding party. She comes over to talk to him and he asks what happened to Bob. She says all the flights were grounded out of his city and he got held up and asked to do more work. They walk around some and happen to go into the reception area for the wedding the next day. Claire goes up to microphone and in her joking around, blurts out "I like you". Drew then says that whoever Bob is, he doesn't deserve Claire, because she shouldn't be a substitute person for anybody and Bob doesn't give her what she deserves. When she asks what she deserves, Drew finds Chuck's wedding toast and reads it for Claire, but he admits it wasn't his words. The two of them end up kissing. They start up to Drew's room, forgetting they left the urn in the reception area! But Claire remembers this before they get to the room and they grab the ashes. They return back to Drew's room where they spend the night together. In the morning Claire goes to leave after she can't seem to wake Drew. As she's getting to her car, Drew finally wakes up and runs after her. Before he can stammer out anything, Claire asks him to get it over with and tell her he loves her already. Drew then tells her about the shoe mistake and how he's about to be a failure and all he can think about is not wanting to be here, which obviously hurts Claire because he's not thinking about her leaving and further that he thinks she'd really care about him having a failure. She leaves and says she'll try to make it to the memorial service.
At the memorial service, Jessie has managed to reunite his band to play at the end. Drew's sister and mom show up, drawing surprise from some of the crowd. Several people give speeches, some of them saying things about "The Californians" as a bit of a joke. Finally, Drew's mother gets up and her speech is practically a stand up comedy routine. She talks about how she's tried to fill her life without Mitch with tap dancing, cooking, working on the car (which was a hilarious scene where she literally gets eaten by the car), and fixing the toilet, but she noticed that no one else cared about Mitch's passing the way she did. Her speech moves many of the Elizabethtown people to respect her and they applaud her speech, which is ended by her tap dancing Mitch's favorite song. Drew steps out of the room to collect himself, and Claire is standing there. She gives him a road map and tells him he needs to take a roadtrip home and really soak up everything that has happened. He wants to be with her but she makes him promise to take the trip and just call her when he gets home from it. Meanwhile, Jessie's band is rocking out Freebird, and Jessie has arranged a big stuffed bird to fly out over the crowd. Unfortunately, the bird catches fire and starts a big fire in the hotel. Sprinklers go off and people start rushing out. Claire uses her stewardess training to direct people towards exits, but Drew and Heather seem to stand in the sprinklers as it were a cleansing rain. Drew looks at Claire and mentally says that this last look definitely sums up Claire, as she has a half crying, half smiling look and then turns away to escape.
After the memorial fiasco, Drew gets in the car and opens the travel map, which is complete with mix music for it. Claire leads him on quite and adventure with his dad's ashes. Drew decides rather than dumping all the ashes in one place, he'll scatter them in many important places, such as a river leading to the Mississippi River, the hotel where Dr Martin Luther King was shot, Dinosaur World. Drew also takes time to stop at a few interesting places as well, such as an old bar in Memphis. He also sees the article on his shoe disaster, which Claire instructs "take 5 minutes to wallow in melancholy, then get over it and move on". As he goes on, he still talks about failure and life and how he wish he'd spent more time with his dad. He finally comes to an understanding of his father's death and for the first time, cries. He had postponed this roadtrip with his dad for his work, and now he was taking it just too late. As a final spot, he rolls down the window, and lets and handful of ashes go as he journeys down the road.
His next stop is the world's 2nd largest farmer's market, accompanied by the direction "Don't get lost!" As he's driving, he sees a highway sign for Route 60B!!!! He finally gets to the market, where he is to look in a dog pamphlet. There's a note inside, telling him to look in one of his shoes on display nearby. He does and the note says "He is a fork in your journey. The directions in the car will guide you home, or you can go to the merry-go-round where a girl in a red cap waits with an alternate plan". Drew remembers the red cap Claire wore when they watched the sunrise and breaks out running for the Merry-Go-Round. After a few minutes on confusion with many people wearing red caps, Drew is about to give up. Suddenly, he looks and sees Claire standing there, grinning widely Drew runs to her and embraces her tightly.