Guiltfree

Bootstraps is the singer-songwriter Jordan Beckett, who released "Guiltfree" on his self-titled debut album. The song is about a difficult breakup where the girl declares she is leaving guilt-free. The singer begins to reconcile this, knowing that time and distance will soon put some space between the two of them. At the time, Beckett was in a healthy relationship, which made his girlfriend wonder just what was going on in his head. "A lot of my music is less of an autobiographical storytelling of something that happened last night, and more of all of the things that are percolating in my brain on any given day," he explained in a Songfacts interview. "'Guiltfree' is a weird song because it's a breakup song, but I was in a really good relationship at the time. I don't know why I wrote that, but it's the best breakup song I've been able to articulate."

With an ambient sound and an emotional lyric, this song became a popular placement for movies and TV scenes. Jordan Beckett is good friends with Sam Jaeger, an actor who at the time was starring in the TV series Parenthood and directing a film called Take Me Home. Jaeger used "Guiltfree" in Take Me Home, which was released in 2011, and in 2012, the song appeared in the Parenthood episode "I'll Be Right Here." The song was also used in the films The Cottage (2012) and Beyond the Mat (2013), and in two 2017 episodes of the series Suits: "Character and Fitness" and "She's Gone." Bootstraps got many more placements over the next several years, many for his cover of "Stand By Me," which was used in the Power Rangers movie and in the TV series MacGyver and Lethal Weapon.

The song was originally called "When You Leave Guilt Free," and had more of a folk feel. When Bootstraps took the demo into the studio, his collaborators Dave Quon and Nate Warkentin suggested he truncate the title to "Guiltfree," so Bootstraps reworked the song.