Dakota Archive

Bobby Caldwell

Drawing from his vast repertoire of rousing R&B, intimate smooth jazz stylings, and big band songs, Bobby has the ability to entertain at any venue, for fans of all ages. In Japan and throughout Asia, he enjoys a feverish popularity, selling out shows and achieving gold and platinum status for his releases in those countries.


Born in Manhattan and raised in Miami, Bobby came from a show business family. His mother and father both sang and were the hosts of one of the first musical variety programs on television, “Suppertime.” Bobby grew up surrounded by show tunes, and these early influences inform his musical choices. As a singer, he has a successful career with numerous solo releases. His songwriting skills have earned hits not only for himself, but also for well-known artists like Chicago, Boz Scaggs, Peter Cetera and Amy Grant, Neil Diamond and Al Jarreau.

Bobby’s timeless classic “What You Won’t Do For Love” has been recorded and sampled by more than 100 artists. A sample of Bobby’s song “Open Your Eyes” appeared in the Grammy nominated platinum rap hit “The Light” by Common. All combined, Bobby’s songs and samples have contributed to over 40 million sales, while artists as diverse as Tupac Shakur, Michael Bolton, Roberta Flack, Go West, Vanessa Williams and Notorious B.I.G. have all paid tribute to the blue-eyed singer in the slouch hat.

• Bobby sings his hit “What You Won’t Do For Love”

• Bobby in Seattle, 2008


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