After several R&B and smooth jazz albums, Caldwell turned to singing standards from the Great American Songbook.

Caldwell was a member of a Miami band called Katmandu who wrote much of their material while also performing traditional standards.

[4][5] "What You Won't Do for Love" on Bobby Caldwell reached the top ten on the Billboard magazine Hot 100 (No.

It was covered by Go West, Phyllis Hyman, Roy Ayers, Michael Bolton, Intro, Boyz II Men and Snoh Aalegra and was sampled by Tupac Shakur for his hit "Do for Love".

The track "Open Your Eyes" from Cat in the Hat was sampled by J Dilla on Common's "The Light" from his 2000 album Like Water for Chocolate.

Singer Boz Scaggs advised Caldwell to write songs for other musicians after TK Records shut down.

Caldwell wrote "The Next Time I Fall", which became a hit for Amy Grant and Peter Cetera,[1] along with songs for Scaggs himself, Roy Ayers, Chicago, Natalie Cole, Neil Diamond, Roberta Flack, and Al Jarreau.

[12] On Blue Condition (1996), Caldwell turned from R&B to recording big band arrangements of songs from the Great American Songbook, particularly those sung by Frank Sinatra.

[17][18] Caldwell wrote and performed songs for the movies Back to School ("Educated Girl"), Mac and Me ("Take Me, I'll Follow You"), Salsa ("Puerto Rico") and its sequel ("Every Teardrop").

Due to what he has cited in interviews as a lower cost of use than the original recordings, his versions of big band standards have appeared in several films.

Aside from a minor role in 1988's Salsa, Caldwell portrayed Frank Sinatra from October 1999 to January 2000 in the Las Vegas musical The Rat Pack Is Back.