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The radio version of "I'll Be", which was released on a CD-single with "Grind Me in the Gears" as the B-side, differs from the album version. Its opening melody is played with electric guitar (as opposed to acoustic on the album) and the vocal and saxophone lines differ. On December 22, 1999, McCain also recorded a version with Warren Haynes on the live concert album from the 11th Annual Christmas Jam, a benefit concert for Habitat for Humanity in Asheville, North Carolina. The album is titled Wintertime Blues: The Benefit Concert.

Although "I'll Be" has become a popular wedding song, McCain said "it's really more of a prayer" written in a moment of personal desperation after a break-up, the idea being that "maybe if I write my future, it'll come true."

At the height of the song's popularity back in 1998 it was featured during a pivotal moment in the first season finale of the hit WB series, Dawson's Creek, titled "Decisions". In 2000, the song was featured in an episode of the television show Higher Ground. The song was used in the masquerade ball scene in A Cinderella Story. It was covered by Dean Geyer on his debut album Rush. In the episode of The Office Here Comes Treble, the song is covered by Andy Bernard's a cappella group. Blake Jenner performed the song in the finale of The Glee Project.

"I'll Be" ended up being a success for McCain in the United States, peaking at #5 on the Billboard Hot 100 after debuting at #7 on the issue dated September 26, 1998. While it was only his second single to chart, it became his first and only Top 10 hit and his biggest hit.

In an interview with Digital Spy, Egan said I chose Ill Be for my second single, as Ive always absolutely loved this song. This song means a lot to me and being able to record it was an honour. Im incredibly excited to be able to perform this for all my fans."