"Timber, I'm Falling In Love" was Loveless' first No. 1 record on Billboard's Hot Country Singles chart and according to her, "I was in my producer, Tony Brown's office, and we were looking for material. He played it and I remember thinking it sounded like an Everly Brothers tune."
Relying on the instincts, Tony Brown brought in a relatively new country artist at the time, Vince Gill, as background vocalist for this song. Loveless said, "I think a lot of people in the industry knew who Vince was, but the public didn't know enough about Vince Gill yet. Before I recorded 'Timber', Vince sang on a song called 'I Did' from my debut album. It was just one of those things that felt like blood. It felt like I was singing with a family member. I thought it turned out to be a wonderful record."