By the Way

That night I sang with Jeffrey Osborne in Gulfport

R&B singer Jeffrey Osborne
R&B singer Jeffrey Osborne COURTESY PHOTO

I’ve never been one to walk away from a challenge, and I have had some mixed results along the way. But that’s the difference between being cocky and being self-confident —I have enough confidence in myself to know that I’m going to be OK if I fail at something.

So when one of Jeffrey Osborne’s guys on Saturday night at the Island View Casino in Gulfport told me Jeffrey wanted me to sing with him and asked me if I could sing, of course my answer was “yes.”

I’ll come back to that.

Osborne is a legendary R&B singer with an incredible voice. Hearing him sing his hit “On The Wings of Love” live is something that should be on the proverbial bucket list of any music fan. He has a way of shaping and bending notes that is incredible.

Osborne also has a pedigree in funk. He was the singer for the popular ’70s funk outfit LTD.

It’s a shame we don’t discuss funk more often. When those musical conversations start and The Beatles or The Rolling Stones are mentioned, Sly and the Family Stone deserve to be a part of that discussion.

Osborne’s set was heavy on LTD songs Saturday night, including the slow jams “Concentrate on You,” “Where Did We Go Wrong” and “Love Ballad.” Of course, the show’s closer, LTD’s “(Everytime I Turn Around) Back in Love Again,” was the jam of the night.

He also paid tribute to his longtime producer, the late George Duke, with a cover of Duke’s “Reach for It” and The JBs’ “Doing it to Death.”

LTD were no strangers to the Gulf Coast during their heyday, playing shows in the area with the Commodores, Brick and Parliament, among other funk legends. The band was also a favorite of Prince, who Osborne said would show up at all of the shows around Minneapolis.

And if all this weren’t enough, he’s also recorded with former Family Stone bassist Larry Graham.

So, yeah, when Jeffrey Osborne asks you to sing with him, you do it.

The song was his mega-hit “You Should Be Mine (The Woo Woo Song),” which his guy asked me if I knew.

“Of course I know that song,” I said.

He told me I would be the last person to sing with Osborne.

When my time came and the spotlight hit me, it was time to go. Osborne introduced me as “his friend Jeff from the Sun Herald who’s a great writer — but I don’t know if he can sing.”

And I sang my part of “woo woo woo.”

Judging from the amount of hugs and high-fives I gave after my performance, I assume my singing was decent.

After it was all over and before I went home to family, I talked to Osborne for a while. He said he really wants to go fishing next time he’s here. We made some plans to do some fishing for redfish the next time he’s here.

Hopefully, he will ask me to sing with him again.

Thanks to Willie Wanzo for the video.