Crooner Bobby Caldwell is about connecting to all kinds of fans

Published on March 23rd, 2021

By Jim Dail

The modern performer faces some of the same dilemmas that musicians have faced for decades: how to reach new fans without disappointing the old ones.

“I worry about betraying my fans,” he said. “I do think they will buy a new album that is a departure from my typical sound, but they may not buy the next ones.”

Caldwell has found his niche in the “jazz” world with a sound that is heavily influenced by many of the legendary crooners.

Caldwell grew up a fan of show tunes, Frank Sinatra and Nat King Cole, among others. When he was still a teen he hit the road to play Las Vegas, then Los Angeles, eventually finding success with the 1978 album “What You Won’t Do For Love.” From that point on, his career was off and running.

His singing style perfectly situated him for the early days of smooth jazz.

“In the early days of smooth jazz – if there is such a thing – a lot of focus was on the vocalists,” he said. “The top of the market was vocalists like Sade and even Sting. I was right there.”

However, jazz radio began to focus more on instrumentalists, particularly saxophone players. Even today, most jazz music is purely instrumental.

But the modern changes in the music business have Caldwell thinking heavily about what to do with his music.

“I don’t want to be pigeonholed in terms of my music and the next album will be somewhat of a departure,” he said. “Let’s just say there will be surprises.”

Part of it is the fact that radio has changed and become a bit too formatted. He misses the days of Top 100 radio where a multitude of artists and genres were well represented.

“Right now, radio can play my record or not play my record, because no matter how often it plays on The Wave or some other station, I’m not going to sell records like someone in the pop field because people who are into jazz don’t buy product that way,” he said. “You can have a smash record, such as something by Chris Botti, who is one of my favorite players, and it might sell 50,000 copies. I can do that out at the shows and on my Web site.”

It has him thinking about what to do next. Is there a Pat Boone does heavy metal in his future?

“No, I wouldn’t say that, but over the last few years I have been thinking a lot about other things to do with my music,” he said. “But again, you do have to maintain the sound and integrity of who you are musically.”

But the real mainstay of Caldwell’s career – and his fans can attest to this – is the live performances.

“You know the kids in the business now have a whole new way of doing things because they have been relegated to doing things

 through Web sites and other ways,” he said. “I mean, Foo Fighters have a tr

And those kids are also attracting people to concerts.avel agency now and that helps them make money.”

“Playing live is what gives you the buzz, the ability to entice people to buy your records,” he said. “If you don’t have that then it’s not going to be a good career for you. So, why even worry about a new album?g to be a good career for you.”

“If I never recorded another album there’s a thought that I could still be okay because of the live shows, but the truth is I don’t think it would work,” he said. “Promoters want to know you have a product so that fans will come to the shows”


Despite concern over the music business, Caldwell does believe that the live music will always be there.

“One thing that is constant is entertainment,” he said, “Even during The Great Depression people still went to shows to forget about problems.”

Someday – though not too soon – Caldwell figures he might retire from constant touring. Will he write or produce? Well, writing certainly has worked out for him. In addition to all his success touring and recording, Caldwell takes great delight in having other people record his songs, a feat that has happened more

than 100 times from Tupac Shakur and Notorious B.I.G. to Go West and Michael Bolton.

Don’t expect to see much producing.

“Producing others is a pain,” he said. “You have to deal with so many other people, not just the artist. If you are writing, you just record it onto your demo and give it to someone and they can put it on record. That to me would be appealing.”


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