Both of these videos feature his big hit “What You Won’t Do For Love”, but they both offer interesting glimpses into his career:
…
Finally, the Bobby Caldwell tribute thread here in Cafe Society from 19 years ago:
I was only ever really familiar with Caldwell for “What You Won’t Do For Love,” but it was, and is, one of my very favorite songs, in part due to his soulful singing on it.
I’d not ever seen a picture or video of Caldwell until the past decade or so, and I admit that I spent several decades under the mistaken impression that he was black, due to his voice.
I, also, thought he was black for decades. I have heard other songs of his songs because my husband loves “cool jazz” but could not name one. Love this song.
I just read an obituary before finding this thread, and I must admit that I’ve never heard of him although I think that I have a wide grasp of pop and soul music (maybe I fool myself). I also never heard THE hit (“What You Won’t Do For Love” definitely wasn’t a hit here in Germany), but I read that many hip hop acts sampled the song, for instance Tupac. What part did they sample? I couldn’t hear anything particularly outstanding in the performance in the video @bordelond posted, but maybe the studio version had some special groove I’ve missed.
Here’s the original studio recording, in case you’re curious. The live performances on those videos are, IMO, pretty close (just lacking some in-studio polish), so it may just not be your cup of tea.
Oh, I didn’t mean that I don’t like the song, I just wondered what made it interesting for rap acts to sample it. Most soul samples in hip hop are short rhythmic parts, but there are also vocal samples.
ETA: I’m just listening to the studio version, which impresses me much more than the live footage, I think mostly thanks to the dramatically better audio quality. Yes, I like the song. I’m a fan of similar music of the time (Steely Dan comes to mind).
@EinsteinsHund , see the article below. Several hip-hop songs sampling Caldwell are mentioned and linked. The Tupac one is titled ‘Do For Love’ though I’m not sure exactly what part of Caldwell’s song they sampled.
Thanks! 
Listening to Tupac’s song “Do For Love” (which Wikipedia notes as having sampled Caldwell’s song), I can hear the bassline, and a bit of the synth, being sampled. There’s also other vocalists (not Caldwell, so I assume recordings made for Tupac’s song) singing the original song’s chorus.
I won’t go down the “Yacht Rock” rabbit hole again here (we had a long thread here, a year or two ago, on what is and isn’t Yacht Rock), but both the Caldwell song, and some of Steely Dan’s songs, are often classified as Yacht Rock (at least here in the States), due to the production level and smooth sound.