In many ways, Reynaldo Gayle is closer to the music than anyone. He’s had a decades-long career in security. He’s worked as a bodyguard for people like LL Cool J and provided security for many clubs and venues in Kingston and the Hudson Valley such as BSP, Truman’s and Bearsville Theater. While Reynaldo has always had an eye on people’s safety, his other eye has been on the stage.

Tomorrow, Wednesday, Nov. 26, at Assembly on Wall Street in Uptown Kingston, Reynaldo, known by his artist name IT’Z REY, kicks off the Thanksgiving holiday with his original music, defined by his disarming baritone voice and raw, vulnerable lyrics.

Rey is a first-generation American. His family is from Panama and he grew up in Brooklyn. He came to the Hudson Valley in 1996 and went to Ulster County Community College. “I always loved music,” said Rey, citing early influences such as Buju Banton, Bob Marley and Prince.

Since then, he’s been at countless shows not as the performer, but as the security. Itching to get on the stage, he’s used his contacts at the clubs he’s worked at to float the idea of performing there himself, but he’s often been shot down. “If I said, ‘Hey, let me open up for somebody,’ they'll say, ‘Stay in your lane!’” said Rey.

But a break has come in the form of the show at Assembly, Kingston’s second largest venue after UPAC. Opening for DJ Shaman Vibez, someone Rey has done security for but will now share the stage with.

“Rey has been such an important fixture of the local scene for such a long time, making folks feel safe and comfortable at venues across the Hudson Valley,” said Drew Frankel, co-owner of Assembly. “At Assembly, we're so excited to be able to give Rey an opportunity to showcase his creativity on stage, and to give our community the chance to see another side of the man we know and love.”

“I appreciate Drew for giving me a chance to perform,” said Rey.

The gig celebrates the release of Rey’s latest single “Sinner.” The song is defined by Rey’s soaring vocals, full of brutally honest soul-searching lyrics, reinforced with a deep-pocketed back beat and weighty piano chords.

“It’s a song about being in limbo,” said Rey. “You're not as good as the best, so you can't go to heaven. But you're not as bad as the worst, so you don’t belong in hell.” In “Sinner,” Rey is taking stock of himself with unflinching honesty. It comes across in his seasoned and heartfelt singing, all creating a balladeering, emotional track.

Other songs, like “All Over,” showcase Rey’s reggae influences, where his singing takes on a smoky, full bodied tone. The instrumental track is mellow and hypnotic, as Rey floats over it with artful phrasing.

Rey has been sharpening his chops with performances and open mic appearances around the Hudson Valley and Capital Region, but he was — like his song “Sinner” foretells — in a kind of limbo. Now, he’s found his way onto the stage.

IT’Z REY and DJ Shaman Vibez will be at Assembly for one night only on Wednesday, Nov. 26. The event is 21 and over, doors are at 7 and the show starts at 8 p.m. Tickets are $14.99 and can be purchased here: https://www.tixr.com/groups/assembly/events/it-z-rey-the-sinner-release-party-164367