He was originally my favorite of the Drake and Kendrick group breaking through. I'm still not sure why he never gained any real traction. I know his first official album was a dud. A LOT of his fans were really disappointed in Live From The Underground. It definitely was not up to par with his mixtapes.
I thought Cadillactica was a good album and I was surprised the title track and Pay Attention never gained any attraction. I thought those were both tailor made, quality singles and they did nothing. After that, I knew it was never gonna happen for him. His subject matter and sound started getting repetitive after that. Krit's still my guy though.
If Country shyt, especially the remix with Luda and Bun woulda been on his debut album, maybe things woulda been a little different.
Had he arrived ten or so years earlier when the south was breaking through, he probably would have sold really well.