Washington State native Nate Mendel is best known for being Foo Fighters bass player. His first solo project under the Lieutenant moniker, was something that Mendel initially had little confidence in. It was Head and the Heart's Josiah Johnson that gave him the necessary assurance. "I've got a lot of respect for (Johnson) as a musician, and he said to me, 'I don't know what it is about this song. It just got stuck in my head and there's something compelling about it,' and he agreed to sing on it," Mendel explained to Billboard magazine. "At that point I was like, 'OK.' That was a stamp of approval that I needed to feel like I'd done something worthwhile."
Mendel told American Songwriter magazine this was probably the most difficult song to write for the album. "Going into the studio I pretty much had things mapped out for all the songs, second guitar parts, third guitar parts, BGV's, everything," he explained. "And that song, I had a suspicion it could be something good, but it only had a couple of parts and guitar line and vocal melodies. It wasn't really a song yet."
"I went in to record it without realizing what the backstop was gonna be or what the backbone was," Mendel continued. "Luckily I had Paige Hamilton come in and play guitar and he added this beautiful guitar riff on top that kind of changed that song and turned into something great."
Kacey Musgraves originally offered "Follow Your Arrow" to her friend Katy Perry. However, Perry thought Musgraves should record the song herself as it seemed, "like something that you would totally say."
Until December 5, 1998, a song had to be issued as a single to make the Hot 100. Aaliyah's "Try Again" was the first tune to top the chart based on airplay alone, without any sales figures being included.