
Robert Hunter Caldwell—better known simply as “Bobby” Caldwell—was a singer, songwriter, musician and producer born in NYC, but raised in Miami, Florida.
Early in his career he traveled to Los Angeles seeking a record deal and wound up getting signed to disco & soul label TK. Ironically, TK Records (home to funk & disco band KC & The Sunshine Band) was based in his hometown of Miami. The label liked the songs he’d recorded for his first album, but told him it lacked a hit. To solve this problem, Caldwell went in the studio for a couple of days and came back with his signature song, “What You Won’t Do For Love.”
Because TK’s primary customer base were African Americans, there was concern that Bobby being white might impact the sales and radio appeal with their main market. So, unlike with many debut album covers, they didn’t have a picture of his face—merely an artistic silhouette of him seated on a bench. When he toured to support the album, he was the opening act for jazz & soul singer Natalie Cole. Many fans were surprised to discover his racial identity, but his popularity only grew.

In the Hiphop and RnB world, he’s been influential beyond his main hit. “What You Won’t Do For Love” has been sampled, of course, by Tupac Shakur in “Do For Love” but a few other songs have also been covered and looped, such as “My Flame” in Notorious B.I.G.’s “Sky’s The Limit” featuring 112 and “Open Your Eyes” for Common’s “The Light” (produced by by J Dilla.) “Open…” was also covered by Dwele & The Platinum Pied Pipers.
If you enjoy any of the tunes mentioned above, listening to his albums (at the least the first two—Bobby Caldwell & Cat In The Hat) will be well rewarded and you will probably discover new favorites.
We lament great any artist who leaves this plane, but fortunately, there is still the work we can still experience and feel enriched by. Thanks for the music and rest in peace, Bobby.