The Singer: Bobby Caldwell can be thought of as a precursor to Rick Astley: a tiny white dude singing with the type of sonorous, rich voice usually found in black soul singers. As an adult contemporary artist, Caldwell is most akin to Michael McDonald and Boz Scaggs (Caldwell even wrote Scaggs’ “Heart of Mine”). It’s no surprise, then, that Caldwell has been laboring in the smooth jazz genre for the better part of two decades. Caldwell still tours and can occasionally be found portraying Frank Sinatra in live Rat Pack revues.
The Song: Powered by a lush electric piano and a chorus of lugubrious trombones and lilting trumpets, “What You Won’t Do For Love” remains one of the more weightless slow jams. Its rhythms are simple and hypnotic, and Caldwell’s nimble phrasing matches the fleet-footed arrangement.
The Video: Like most pre-MTV videos, this one showcases the raw glory of a blank soundstage. Sitting on a park bench, Caldwell emerges from the darkness (perhaps a nod to his racially confusing voice?) wearing a suit, fedora, and truly enormous knit tie. From there, Caldwell vamps on guitar and piano, looking like a cross between Chuck Mangione and Peter Falk’s Columbo. And if anyone can tell me a) why there is a caged parrot on the park bench and/or b) why Caldwell places his fedora atop it, I’d love to know.
Hipster Cachet: “What You Won’t Do For Love” has been sampled and covered countless times, most notably Aaliyah’s “Age Ain’t Nothin’ But a Number” and 2Pac’s “Heaven Ain’t Hard 2 Find.” Another Caldwell gem “Open Your Eyes” was sampled in Common’s “The Light.” Video below:
-- Christian Schaeffer
