This film was inspired by Cameron Crowe's visit to his own father's grave. It was his first trip to Kentucky since his father died 16 years earlier, and he found himself overwhelmed with emotion.
Cameron Crowe had written the role of Drew Baylor with Orlando Bloom in mind. When Crowe originally offered Bloom the part, Bloom was unable to take it due to scheduling conflicts with Kingdom of Heaven (2005). Crowe then cast Ashton Kutcher in the part but later felt that Kutcher and co-star Kirsten Dunst had no chemistry and decided to let him go. Crowe then pushed his January 2004 start shoot date back to July 2004 for a summer shoot. Many young actors that included Seann William Scott, James Franco, Colin Hanks and Chris Evans auditioned for the part of Drew. Scott was seriously considered and nearly nabbed the part but Crowe pushed to get Bloom instead. When Bloom was able to work the film into his schedule, Crowe cast him in the part.
While filming, Orlando Bloom first tasted Ale-8-One, a soda produced only in Winchester, Ky. He enjoyed the drink so much that he started receiving shipments to his personal address.
While shooting a scene in a cemetery with actors Orlando Bloom and Kirsten Dunst, filming was interrupted due to an unexpected rain storm. Cameron Crowe suggested they shoot the scene anyway because it looked more beautiful and natural.
Jesse's band comprises members of Kentucky's native band My Morning Jacket who are also featured on the soundtrack.