What's the biggest risk you've taken with your career?

The single choices. I remember telling the head of Warner Brothers that if they'd just make a video for 'Ol' Red' ... and if it didn't work, they could drop me from the label. I talked him into it, which was a big risk at the time because this was in 2001 when there really weren't any songs about going to jail, killing somebody ... or dogs! It could've easily backfired. If we hadn't made that video, people wouldn't have gotten the song.