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 endeavor, Smile, which didn't feature his own new song collection between The Road to Ensenada (1996) and My Baby Don't Tolerate (2003), also included a 1998 cover album, a 1999 live album, a 2000 movie soundtrack, and an anthology. This release suggested that Lovett might be facing writer's block.