- Actor-Shared Background: Chiles parents are revealed to have served time in prison. Leighton Meester was in the same situation.
- Dueling Movies: With Crazy Heart.
- Irony as She Is Cast: Tim McGraw, a successful country singer, is the only one of the four leads who does not sing in the film.
- Missing Trailer Scene: A music video for the song "Summer Girl" contains a few shots of Chiles performing in the bar that don't appear in the final film. She's shown only performing the end of the song in the actual scene.
- Oscar Bait: Troubled country singer? Check. Mentally ill female? Check. Redemption Quest storyline? Check. It didn't take, and only got a Best Original Song nomination.
- Shown Their Work: Garret Hedlund and Gwyneth Paltrow learned how to play guitar and underwent extensive vocal training to believably play country singers.
- Star-Derailing Role: The successive failures of this movie, Monte Carlo and That's My Boy ended any chance Leighton Meester had at becoming a bankable Hollywood star. She has found a little more success as a singer.
Trivia / Country Strong