The song features harmony vocals by Trisha Yearwood. Garth provided the following background information on the song in the CD booklet liner notes from The Hits:
"Shameless" was the longest shot we took with a song. I was talked into becoming a member of a CD club... you know, the 40,000 CD's for a penny deal. With those clubs they write you with the selection of the month. If you don't write back and cancel, then they send it to you and charge you for it. I was on the road for six months with no one to check the mail and came home to find six compact discs in my mailbox. Storm Front by Billy Joel was one of them. I hadn't listened to Billy Joel since the late seventies, probably since Glass Houses. I fell in love with the album and fell back in love with Billy Joel's music. One of his songs really captured me, a song called "Shameless." I kept watching it, and when he did not release it as a single, we contacted his people in the hopes that we could cut it. His people sent us a letter acknowledging that he knew who I was and was very honored that I was cutting it. That was quite a compliment for me then, as it is now. My hope is that Billy, as writer, hears this cut and says, "Yeah, man, the guy's got balls."
Garth Brooks performed "Shameless" with Billy Joel during Joel's Last Play at Shea concerts in 2008, and after Brooks performed it in his Central Park concert in 1999, Joel came out on stage and they sang a duet of "New York State of Mind." In June 2010, Joel and Brooks performed the song together again when Brooks was inducted to the Songwriters Hall of Fame by Joel.
Garth Brooks version
Stephen Thomas Erlewine of Allmusic described Brooks' rendering of the song favorably in his review of the album, saying that Brooks "made his '70s rock influences more explicit" by "transform[ing] the song from a rock power ballad into contemporary country."