Mr. Fedora

“He left a great legacy and one of my best friends some awesome theme music.” Willis Foster, my ‘brother from another mother’, wrote this message to me on Facebook messenger along with the tragic news that Bobby Caldwell had died on March 14, 2023. I was initially stunned when I saw the message. I was at work and I had no idea he had passed. Immediately I began to press the rewind button in my mind to 1980; the very first time I heard Mr. Caldwell sing. I was nine, maybe ten when I heard his classic song on the radio: What You Won’t Do for Love. I was preparing for my school day and I heard the song on the radio station that still exists today: Foxy 107. Obviously, no pre-teen knows anything remotely about the subject of love, but, innately I knew that this was a special song. I remember he sounded so smooth when he sang, and the album cover was something I had not seen before.

Mr. Caldwell, in his trademark fedora, was silhouetted. There was a sense of mystery that seemed to surround him on the album cover. I had no idea who he was (not that it mattered), all I knew back then was that the man could just flat out sing. Arguably his greatest song, “What You Won’t Do for Love” became one of my favorite songs to listen to. As I got older, I branched out to other great songs by Mr. Caldwell: “My Flame”, and his classic covers of “Don’t Ask My Neighbor”, and “At Last.”

To this day, the music of Bobby Caldwell serves as a bridge to several generations; his songs are timeless. You can place any of his melodies in any era, but for me, my “go to” Bobby Caldwell song will forever be the hit that artists continue to cover and the song that embodies the unmistakable sound of Mr. Fedora. Willis Foster said it best: “Rest in Power, Bobby Caldwell.”