One of the most sampled songs in the pop repertoire, “What You Won’t Do for Love” was the lone Top-40 hit for New York-born singer Bobby Caldwell.
Born in Manhattan in 1951, Bobby Caldwell began his career as a rock singer, opening for Little Richard, touring with Johnny Winter‘s band and recording with the likes of Rick Derringer (who included Caldwell on his All-American Boy album). Caldwell also appeared anonymously on countless jingles and TV songs.
Twenty years of living in the musical shadows ended when Caldwell recorded his first solo release on Clouds Records in 1979. Included on the album was the George Benson-esque slow jam “What You Won’t Do for Love.” Hoping to win airplay on R&B stations, Caldwell’s identity — that is, the fact he is white — was obscured by photos of him shown only in silhouette, for example.
The strategy worked with Caldwell placing his cut at #6 on the R&B charts and, as his only pop hit, at #9 on the Billboard Hot 100 chart. “What You Won’t do for Love” has since went on to live a second life, having been sampled by everyone from Aaliyah to 2Pac.