Howie D of the Backstreet Boys credits his older sister Pollyanna Dorough for inspiring him to be an entertainer. Pollyanna, who is also a singer and vocal coach, is one of the songwriters on Howie's solo children's CD. "Pollyanna's Shadow" reflects her slight frustration of having little Howie follow her wherever she goes, and she encourages him to step out of her shadow and take the lead. Broadway singer Lisa St. Lou, also a cowriter on the CD, voices Pollyanna's perspective on the track.
Howie spoke about the song in his 2019 Songfacts interview
: "I just followed [Pollyanna's] footsteps as a little kid. At the young age of 6 or 7 years old, I was in my very first musical with her, The Wizard of Oz
. She was playing the Good Witch at 17 or 18 years old and they needed a bunch of people. They had their younger brothers and sisters play Munchkins, so she asked me to come out and be one of the Lollipop Guild guys. I was actually just a Munchkin at first and when they asked whoever wanted to audition, believe it or not I had the nerve to want to do it, and I was truly Mr. Shy. But I think about how I would always sing with her in church as a little kid. I couldn't even read, but I'd memorize the words. When I was like 6 years old, I'd be singing with her in the folk mass on Sundays. I truly was my sister's shadow. I would follow her wherever she went. I would even go to the contests that she would compete in or she would take me as her show-and-tell for school. I love her so much."