When an artist has a proven sound and a legacy hit to go with it, no one would complain if he decided to play it safe and stay with it. For vocalist Bobby Caldwell the “sound” goes back to 1978, and the legacy hit is “What You Won’t Do For Love.”

The song was Caldwell’s debut single, and it was so successful that the record label eventually changed the name of the album it was on from “Bobby Caldwell” to “What You Won’t Do For Love.” Caldwell has been a successful working musician, songwriter and recording artist ever since.

Behold, then, Caldwell’s latest album, “Cool Uncle,” which is a dramatic departure for him. “Cool Uncle” is a creative partnership with three-time Grammy Award-winning record producer Jack Splash, a man who names Caldwell as one of his musical influences and is young enough to be Caldwell’s son. Splash’s credits include projects for Cee-Lo, Jennifer Hudson, Alicia Keys, Kendrick Lamar and John Legend.

“I chose to do (‘Cool Uncle’) for a number of reasons, the biggest being that he’s 20 years my junior and he’s plugged into a certain aspect of this business that I’m not,” Caldwell said in a call last weekend from a tour stop in Hollywood. “For the first time in my career I allowed somebody else to, like, ‘produce’ me, which he’s qualified to do, and we got along famously. For the music and the artwork I kind of stood out my own way.”

Caldwell and Splash recorded “Cool Uncle” in a series of sessions, with breaks to accommodate Caldwell’s tour schedule and Splash’s commitments to other artists.

“We’re always on the road,” Caldwell added. And “the road” is bringing Caldwell to Blue Note Hawaii in Waikiki for four nights. Caldwell has played at the Blue Note clubs in Japan and says he likes the intimacy of club gigs.

“There’s a sense of intimacy that you don’t get in theaters, and, not to blow our own horn, but it is a well-crafted show. People will not be disappointed. That’s why we’re still out here performing because the constituency we have out there, they demand it, and we enjoy it just like we did 35 years ago. We enjoy it still.”

The music business has countless stories about how songs were written, groups were assembled and hit records were made. Some stories are strictly the stuff of legend, others are true. Caldwell confirmed that the fabled origin of “What You Won’t Do For Love” is true. Yes, he wrote it on deadline in about 15 minutes after the owner of the record label said he liked Caldwell’s album but didn’t hear a “hit.”

Caldwell and the musicians went back in the studio.

“After all this blood, sweat and tears, I went in, almost in haste, and put this song together, and lo and behold, that ended up being a hit.”

He describes the writing progress as “a personal exorcism from getting dumped by a woman. We’ve all been there.”

“What You Won’t Do For Love” was not only a hit for Caldwell as a recording artist in 1978. As of 2016, it has been recorded or sampled or interpolated one way or another by more than 40 recording artists and producers. Caldwell gets a royalty any time someone records the song or uses samples of it.

“Any version is flattering, that people would think enough of your stuff, your material, to remake it in any shape or form, but one of my favorite recordings of it was Go West (in 1993). We like walking to the mailbox (to get royalty checks).”

Caldwell’s versatility as a singer and recording artist can also be appreciated in “After Dark,” which was released in 2014. On it, he performs with a 17-piece “big band” and puts his personal touch on several songs associated with Frank Sinatra.

“This is the third installment of us visiting The (Great) American Songbook, if you will. I grew up in a family where I was pretty much surrounded by the music of Ella Fitzgerald, (Frank) Sinatra, Dean Martin, Tony Bennett and Johnny Mathis — and for the most part my household was Sinatra Headquarters. It influenced me heavily and I was fond of the songs of the great composers of the day and still do have an affinity for that (music).”

Asked about the impact of Facebook, file sharing and all the other “platforms” for distributing music, Caldwell said records were being stolen and sold illegally back in the “good old days.”

“A lot of people will argue that it used to be better in the past, but I think it can more be called a business today than it ever could in the past. I think the artist is forced for a multitude of reasons to get into his own stuff and control his life, and I think in doing that artists become a lot more knowledgeable.”