At the end of the movie, Drew's voiceover says, "The motto of the British Special Service Airforce is 'those who risk, win'." The unit is actually called the "Special Air Service", it is a special forces unit and not an airforce at all, and the motto is "Who Dares Wins".
At the memorial, when the people are leaving the room because of the fire, there's a shot of a woman taking away Drew's father's picture, a giant portrait in black and white. In the next shot, the picture is seen at the back of the room.
When Hollie is giving her speech at the memorial, we see her walk across the stage and as her pant legs sway they reveal pointy toe stilettos - clearly not suitable for tap dancing. However, when she puts the microphone down and begins her performance, she is suddenly wearing tap shoes.
When the neighbors are loading Drew's belongings from the curb into their car near the beginning of the movie, there is a white box with holes in it (similar to a large wine rack). One of the guys loads this box into the car, but in the next shot it is back on the sidewalk with stuff piled on top of it.
When Drew is arriving at the funeral home in Elizabethtown, he grabs his jacket and then closes the door of the vehicle. It then pans to his cousin Jesse for a few seconds. When it returns to Drew, he now is holding the blue suit.
When Drew is on his road trip that Claire planned out for him, we see a shot of him driving along a road, a lot of dust rising from the car behind him, due to driving on a gravel road. In the next shot, we see that he is clearly driving on a paved, cement road.
When Claire and Drew are in the ballroom, Claire is holding a champagne glass. When she steps up onto the platform area of the main table, she sets it down. Drew lifts her off and puts her down, and she doesn't have it, but in the next shot she is holding it again.
During the scene where the band is playing "Free Bird" and the hall catches fire, the banner across the stage burns in two and falls to either side. Later in the song there is a long shot of the band onstage and the banner is intact.
When Drew is on his trip planned by that Claire, we see a series of scenes suggesting that a lot of time passes. Drew browses through the book, changes CDs and from time to time takes a look at the father's urn. In these moments the book is opened always on the same page.
After Orlando Bloom gets off plane he gets lost in his car. He starts banging the wheel in frustration. While filmed from the inside of the car you see a fence in the background. In the exterior shot of the car the fence is on the opposite side.
When Claire sits down with the urn with the ashes, she reaches across her body with her right hand (as she is holding a glass in her left hand) and touches the urn saying "Hello, Mitch". In the next shot, the glass is in her right hand and her left is on the urn.
When Claire is leaving Drew's hotel room in the morning she has a flower in her right hand. In the next shot she takes the imaginary photo with empty hands. After this she walks away and rests the flower on the dressing table.
Towards the end of the movie, when Drew is driving, the camera shows a Wichita sign next to road. For a second, the very dirty top of the windshield (that the wipers can't reach) is visible. In the next shot, showing Drew from the side, the windshield is totally clean.
When Drew is on his road trip home, he stops to spread his dad's ashes. The urn is tucked under his left arm and his right hand is full of ashes but the lid is already back on the urn. How did he replace the lid before spreading the ashes?
While Drew is Driving into Elizabethtown and is waving to all the
townsfolk you can see reflections in the windows of some buildings, The reflections are of the car that Drew is in and it is on a trailer with a camera attached to the bonnet.
The movie is set in 2005. But when Drew steps out of the car upon reaching the funeral home, the sound of 17-year-cicadas is very evident. Cicadas were not active in 2005, however, they were the year before.
When Drew is looking at his dad in the casket you can see his "dead" dad quite clearly crack a smile. However, based on the context of the story, this clearly was an attempt by the filmmakers to show Drew daydreaming and/or hallucinating when faced with the emotion of seeing his dead father.