After a near twenty year creative partnership, Yoakam and bandleader Anderson went their separate ways after recording Population Me in 2003 when the singer opted to tour with a small group rather than a full band.

This was in part due to financial necessity after Yoakam bankrolled his 2001 film project South of Heaven – West of Hell, which was a critical and commercial bust.

Yoakam cited Simon and Garfunkel’s masterpiece Bridge Over Troubled Water as an inspiration for the sound he was going for as a producer, detailing to biographer Don McCleese: I think I did some things with EQ differently.

The song talks about actually having a band, performing live music, or cutting a record, or at sixteen waiting for that opportunity...And it's not easy to get back to that place, that space...[7] Although steeped in Bakersfield honky-tonk, Yoakam chose to experiment on several tracks, the most obvious examples being “She’ll Remember,” which contains a synthesizer introduction and Yoakam speaking in a quasi-British accent until the songs falls into heavy honky-tonk mode, and the heavily-orchestrated losing track.

His acting chops come to the fore again on the storytelling title track as he assumes the role of an awestruck bystander describing the apoplectic woman in the song.