The second single from Brad Paisley's debut album, Who Needs Pictures, this became his first Country #1 in December 1999, holding the top spot for one week.
The song was penned by Paisley with his frequent co-writer and best friend Kelley Lovelace and based on the latter's relationship with his stepson McCain Merren. "'He Didn't Have to Be' was probably the most life-changing three minutes that I've ever written, because I really believe we wouldn't be sitting here anymore talking," Paisley said. "Maybe we'd be sitting here with me having written a #1 song for somebody else, but I don't think I'd still have a record deal without that song. It broke the ice for me with radio. It was like you could see potential in it, and that's an important thing. I was really lucky, it wasn't like we knew what we were doing. I just happened [to write] that with my best friend from the bottom of my heart about his situation."
This was written from the perspective of a son of a single mother; we hear how the single mom begins dating a new man who immediately builds a relationship with the child as well. Lovelace co-penned it from personal experience having become a step-dad to McCain Merren when he married his wife, Karen. According to an interview with the songwriter in USA Weekend magazine, Paisley said to him, "Let's make a song about you two that will make your wife cry."
Top session drummer Eddie Bayers played on this. The winner of the Academy of Country Music's Drummer of the Year Award for eight straight years, Bayers has played on songs by the likes of John Denver, George Straitt, The Beach Boys, Garth Brooks, Glen Campbell, Kenny Chesney and Elton John.
The song was later included on Paisley's 2009 album, Playlist: The Very Best of Brad Paisley, as well as on his 2010 Hits Alive record.