Songfacts®:

• Drivin N Cryin is a Southern Rock band who have been together since the mid-1980s. This track, from their third album Mystery Road, is their best known track. Frontman Kevn Kinney, who penned the tune, explained the story behind the song:
  
  "It's just about a latchkey kid whose mother is dating and they have different rules. It's got a little bit of 'Romeo and Juliet' to it, but it's mostly about my sister's life, but it's also about everybody's life, that's why I think people identify so much with it. There were a lot of single parents at that time. Divorce was kind of new back then and that happened to a lot of kids."
• R.E.M's Peter Buck was originally earmarked to be the producer of the Mystery Road album. He was a friend of the band, and they recorded demos together. However, Island Records refused their choice and picked Scott McPherson to be the producer.
• Darius Rucker's fifth album, When Was the Last Time, features a cover of this song. "When it was played in the bar, every single person in the bar was singing and hugging their best friend," Rucker told Nash Country Daily. "I've wanted to cut that song since I came to Nashville, and I kept saying I was going to cut it someday."
• Rucker's version features guests Jason Aldean, Luke Bryan, and Charles Kelley. It was the latter who persuaded him to record it. "Charles calls me out of the blue and says 'Hey man I just listened to this Drivin' N Cryin' song, you should cut that 'Straight to Hell,'" Rucker recalled to Taste of Country Nights. "I thought that was the universe telling me to cut the song. And at the end of it he's like, 'I wanna sing it with you!'"
• The original Drivin N Cryin version of "Straight to Hell" is about six minutes long. Rucker shortened his recording as he thought he might release it as a single.
• Luke Bryan, Charles Kelley and Jason Aldean joined Darius Rucker for the video, which features the country stars in a speakeasy during Prohibition back in the 1920s. Rucker said:
  
  "I went to Capitol and said, 'I've never asked for anything, but if you guys would just do me a favor. Whether 'Straight to Hell' is a single or not, I really want to make a video, and I want it to be a Western video.' I was thinking horses and stuff. I'm really glad they weren't thinking that [laughs], 'cause I don't want to be riding nobody's horse out there. I'd kill myself. It was so much fun."