The Magic Of Bobby Caldwell

Not long after the 48 Record Bar opened, I met a customer who told me that he was someone’s boyfriend immediately after their previous boyfriend had been — you guessed it — Bobby Caldwell. My heart went out to him. 

For Caldwell was not just a man who deeply understood R&B and the way its contours both mirror and enhance our lives, but the evidence also suggest that here was a man who knew romance, wild creativity, and not for nothing, a level of sophistication few of us ever move through this world with, for even moments let alone a lifetime. Caldwell made a career out of all of it, was a franchise player, and his songs echo with us still, even gaining in popularity as we move through this present timeline. 

Dude brought it up in the first place because we were spinning, as we often do, The Cat In The Hat, Caldwell’s 1980 sophomore LP. It’s one of 48’s sure-shot records, and everytime we put it on, you can hear someone (sometimes multiple persons) down the bar make some sort of emotional sound indicating positive feeling. Dawwwwww! Yessssss. Oh word?

We get it; it’s that kind of record. And so when we discovered that we could lay hands on this wonderfully produced reissue of it on the UK’s Be With Records, pressed on high-quality wax in Holland, we took steps immediately. If you like this place that we have here, wait til you go to the musical place that is The Cat In The Hat.

Its tracks have been sampled by Common/J Dilla, Kendrick Lamar, Murs, and many more, and listening through, it’s easy to understand why. Caldwell was superb at conjuring a feeling married up to a can’t-miss hook, and for our money, this is him at his very best. 

Recorded at Criteria Studios in Miami, The Cat In The Hat models the warm jazz tone given a nightlife panache that characterized all the best stuff on TK Records, the label for whom Caldwell initially made the LP. It went gold in the States and platinum in Japan, and is part of a 4-album run of Caldwell’s stuff that now sounds iconic, and influential all over again as this kind of jazz/soul/R&B melange gets expressed by a whole new generation of artists. 

After that run, Caldwell continued to make music for the rest of his life, not just making his own albums, but also writing songs for big-name artists and movies alike. In the 1990s, as a performer, he took on the Great American Songbook and Frank Sinatra alike, playing that music for the rest of his life in Las Vegas. But behind it all, at all times, was a one-of-a-kind soul artist. 

As to the guy who was his girlfriend’s next boyfriend? I don’t know, but I don’t think I even need to tell you: She wasn’t with him that night. 

— Joey Sweeney

Note: These words originally appeared as the liner notes for the 48 Record Bar Record Of The Month for April 2024. To learn more about our ROTM program, click here.