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). Other projects included a 1998 cover album, a 1999 live album, a 2000 movie soundtrack, and a 2001 anthology. The release of Smile led some reviewers to speculate the Lovett might be experiencing some sort of writer's block.
Lovett's fifth project, Smile, which didn't include his own new song collection between his Grammy-winning album The Road to Ensenada (1996) and My Baby Don't Tolerate (2003), also featured a 1998 cover album, a 1999 live album, a 2000 movie soundtrack, and an anthology. This release led some critics to speculate that Lovett might be experiencing writer's block.