Continuity mistake: At the cemetery, when Jessie and Drew walk over to Dale and Charles Dean, who are standing at the burial plot, the men's positions move a few feet between shots. (00:27:00)
Continuity mistake: During Mitch's memorial, after Claire tells Drew, "I want you to get into the deep beautiful melancholy of..." there is a shot of the audience as Ruckus plays Freebird, and Hollie and Heather have their backs to the stage as they speak to someone, while everyone else is going wild. When it cuts to close-ups, both face the stage and Heather is jumping up and down yelling, and Hollie is laughing. (01:39:05)
Continuity mistake: When Drew is standing over his father's coffin, the position of his bangs keeps changing every time they cut back to him. Throughout the film his hair changes position in consecutive shots.
Continuity mistake: When Jessie hugs Drew in the parking lot, there is an outline of the suit within the garment bag, which hangs from the single hanger that Drew holds. However, when Drew greets Dale and Charles Dean the bag is thicker and he holds two hangers. (00:26:55)
Continuity mistake: When the sprinklers go off, Mitch's ex-fiancée grabs his portrait and runs out, but in the next shot of guests running out of the ballroom, you can still see it in the background. (01:41:00)
Factual error: In the scene where Drew begins his road trip to Elizabethtown, you see him traveling across a bridge into the city of Louisville. Elizabethtown is located south of Louisville as is the airport. Unless he was already lost, there's no way that he would have traveled that particular route. (The scene was obviously used to highlight the city in the movie).
Continuity mistake: When Drew stands in front of the Lorraine Hotel holding the photograph, the way he grips it noticeably differs between shots. (01:47:10)
Continuity mistake: After Drew rescues Samson from the car, when everyone stands together in the house "discussing" it, Bill Banyon walks in, and everyone's position changes, especially Samson's. Every time it cuts, either Jessie has his arms around Samson or Samson stands beside Dora, with her arms around him. (00:36:15)
Audio problem: In Drew's hotel room, while he sleeps, when Claire and her red sandals stomp over towards the TV to try and wake Drew, she is making loud stomping noises as if she and her heels are stomping around on a bare wood floor, but there's carpet on the floor. Obviously deliberately done for the humor. (01:20:20)
Audio problem: Outside the hotel, Drew tells Claire about the "fiasco" and says, "And by the way, I didn't say million. I said billion!" In the next shot facing Claire, he is still talking though nothing is heard. (01:23:55)
Continuity mistake: When the airplane lands in Kentucky, Claire hands Drew the hotel coupon with her phone numbers written on the back, which he looks at as he walks through the terminal. When Drew phones Claire from his hotel room, he holds up the coupon and everything differs, even the cute dotted line around "don't miss 60B!!" is now a solid line. (00:23:00 - 00:43:50)
Continuity mistake: In Drew's hotel room, when Claire tries to rouse him from his sound sleep, he doesn't wake, but Drew's position, blanket, pillows, etc., change in the following shots. (01:20:15)
Continuity mistake: In the hotel we see Drew, while on the phone with Claire, as he washes his garish orange-white socks, and hangs them to dry. A few shots later he is wearing them, and later (still on the phone with Claire) he wears dark green socks. (00:48:45)
Continuity mistake: When Claire greets Drew and then takes a seat beside him on the airplane, the part in her hair repeatedly differs between shots. Later, when Drew and Claire run back to the ballroom, where they left Mitch, her hair is pulled into a barrette, and some of her hair alternates between loose or not. This type of thing occurs numerous times in the film. (00:17:20)
Continuity mistake: When Drew was standing over his father in his coffin, there is a wide shot of Drew, and his mouth is slightly open. It then cuts to a head shot of Drew, and his mouth is suddenly closed, with no time to change between shots.
Continuity mistake: A wireless microphone was laid down near the front of the stage so the speaker could dance. In many subsequent shots the microphone changed orientation and location. (01:34:50)
Audio problem: On the flight to Kentucky, Claire tells Drew, "Cause the roads around there are hopelessly and gloriously confusing." When she says the words, "There are hopelessly" it cuts to Drew's close-up as she pats his arm and smiles broadly, obviously not saying the words we hear. (00:17:05)
Continuity mistake: At Mercury Headquarters, when Phil speaks of "Sh*t hitting the fan globally," and reads the memo from the DCS CEO, in Drew's close-ups he has a bruise on his upper lip, which is gone in previous and following close-ups. (00:08:25)
Continuity mistake: In his hotel room, when Drew phones his sister and leaves a message, in the shot from behind him the box in front of him is open, but in the next shot from the front it is closed, and so on. (00:42:40)
Continuity mistake: When Drew shows Claire the site of Mitch's memorial, there are tables, chairs, balloons etc., set up in the ballroom from Chuck and Cindy's rehearsal. Balloons' and chairs' positions change, disappear or reappear between shots here and when Drew and Claire run back to get Mitch.