Jack Ingram found that success came easy with his diligent work ethic. He was earning six-figures just playing regionally. But there wasn't a lot of fulfillment in it for him. There were also elements of the Texas scene that didn't suit Ingram or his artistry. "I always suspected that I had an audience that didn't really like who I was ultimately going to be," he explained in an interview with Texas Monthly.
"They were there for the party," he continued. "That's where it gets a little strange for me. You want to lump me in with everybody playing that scene? I can't control that. But I was also very aware that it wasn't cool to tell people why I thought that was offensive. So I just told myself, 'I don't know how long it's going to take, but when I'm done I'll either have failed to reach my goals or I will reach them — and they won't care that I got my start playing frat country.' I figured, if you want to come at me because of the early audiences I played for, I'll take it till I'm great. And at that point, it'll be a footnote."
In 2005, big changes came when Ingram signed to Big Machine Records, once home to Taylor Swift. A year later, he delivered the label's first hit, "Wherever You Are," the first number one for both Big Machine and Ingram on the Billboard country singles chart (per CMT). He wound up parting ways with the label in 2011, with Ingram wanting to take his music in a different direction.
