Smile was the fifth project by Lovett that did not introduce a new collection of his own songs during the expanse of time between his 1996 Grammy winning The Road to Ensenada and My Baby Don't Tolerate (released later in 2003).

The release of Smile led some reviewers to speculate the Lovett might be experiencing some sort of writer's block.

[1] Another possibility is that Lovett was taking it easy following a 2002 injury from an accident involving a bull on a family farm in Texas.

During the incident Lovett's leg was broken in 20 places.

A fracture to his thumb also left him unable to play guitar for an extended period.