Every so often on Facebook, like every few months, I like to do a “Bobby Caldwell is white” check. What’s that? Well, it’s where I randomly toss out “Hey, did you know Bobby Caldwell is white?” and like clockwork there is ALWAYS some group of black folks who, at that moment, learn the truth that the rest of us discovered at varying points in our lives: Bobby Caldwell, the man who sings and shared with the world “What You Won’t Do for Love” is, in fact, a white man. Say, heffa, say what???
I know—let it soak in. It’s true. It’s one of those discoveries that leave black people’s souls tattered and in search of closure with exes. I was in college when I found out. One of my boys randomly mentioned that Bobby Caldwell was white—this was before the internet—and I remember a discussion erupting as to the veracity of said rude-as-fuck statement. It ain’t like we had Google or albums lying around that could prove it one way or the other. Hell, even if we did have the album, the cover for 1978’s What You Won’t Do for Love features a little silhouette shadow man sitting on a bench. We don’t see his face. That shadow man?
Because silhouette shadow man.
Thing is, that one convo put that seed into my mind, forcing me to listen to him differently. Not in a bad or negative way, but trying to see if he sounded, ya know, white. To me, he didn’t. But the curiosity was there. So when I did eventually find out, it didn’t rock my core like it has some other people.
I tell you, I saw one man find out and, well, let’s just say I’ll never look at guacamole the same ever again. It’s important to note here that nobody who finds out the truth is upset that Bobby Caldwell is white; if anything, it just means he gets one of those probationary cookout invites off break while he gets vetted for problematic behavior.
No, usually finding out he’s white is akin to a spiritual awakening and absolute disbelief, followed by a pretty incredulous “Bobby Caldwell is ... white? HOW SWAY?” People really ask Sway.
Honestly, I’m amazed at how it’s still a point of discovery for so many. Nearly all of us listen to music via YouTube, and there’s even a video with a pretty doggone white white man singing and jamming along to his savory concoction. I get it, though—the song “What You Won’t Do for Love” is nearly perfect in every way. You can listen to it in a car, at a bar, on a boat, sniffin’ coke, at the job, while you rob—well, you get the point.
What’s most interesting about Bobby Caldwell and finding out he’s white is how often it comes up in black circles, almost as if it’s one of the universal black discoveries. At some point, everybody black finds out the truth we didn’t even know we were seeking. It’s a thing.
In fact, I just did a Google search for “Bobby Caldwell white,” and within the last two hours of this search, Bomani Jones and Wesley Lowery both have tweets about him being white and black folks’ discovery of it. Like, literally, RIGHT NOW, people are discovering this fact AND being amazed that people are discovering this fact, and I have no idea what time it is that you’re reading this. But literally, it’s happening right now. It is the black happening.
There will be stories told to children about the time they found out Bobby Caldwell is white because, let’s be real, “What You Won’t Do for Love” will play wherever black people congregate until there are no more congregations.
What is also interesting is that people don’t make this discovery through other songs of his, considering that he’s been sampled by the likes of Biggie (“Sky Is the Limit” sampled “My Flame”) and Common’s most famous song, “The Light,” is based on Bobby Caldwell’s song “Open Your Eyes,” among a whole SLEW of others; Dilla sampled more than a few times. And who doesn’t love Dilla?
One of the black community’s great solved mysteries still has legs, and it’s entirely possible that until this reading, some of you—pick up your jaw; I opened your eyes (pun intended), like, six paragraphs ago—some of you had no idea. Welcome to the party. For the rest of you ...
When did you find out Bobby Caldwell was white?