JACKSONVILLE, Fla. – Bobby Wintons Jr., professionally known as Bob on Keys, traces the sound that has taken him from church pews in Apalachicola to Billboard recognition and international tour buses back to one simple beginning: family, the church and an 88-key keyboard.

Watch the full interview with Wintons below.

Wintons said his earliest memory of music is playing the drums for his church, which he credited his mother for getting his start with the instrument. He said he wasn’t that good of a drummer, so he was allowed to play the slow songs.

“She sings, writes, does plays, she does her own music so she’s a super huge influence on me as a musician,” he said.

His Uncle Toby plays the keys and he has many other family members who sing as well.

Wintons switched from drums to piano around age 12 or 13. He later moved with his family to Jacksonville after they connected with The Potter’s House, where his mother taught and he attended the Potter’s House Christian Academy.

Expanding his musical horizons through collaboration

The church foundation gave way to other musical rooms. In high school, he played jazz with a local band, learning key basslines and standards that would expand his musical vocabulary.

“My first instance of any music outside of church was jazz,” he said.

Playing Friday night gigs as a teenager gave him early experience recreating and respecting songs across genres.

That broad musical education — from gospel to jazz to trap — informs his approach in the studio.

Though he’s not from Jacksonville, he’s worked with local artists Akai and Ebonique. He said it’s important for him to build community among the artists right in his backyard.

“One of the main things that I like to do is collaborate with different artists...and bring a different side that they might not be used to working with other producers,” Wintons said.

He described his creative process as half random experimentation and half intentional work tailored to the artist in mind.

Collaboration is central to his work. Wintons said a period of studio sessions with producers DJ Shab and Keem Turbo helped him develop a reliable formula.

‘It happens fast’: Billboard 200 recognition

“By the time [Keem] got to the drums it was like, ‘Yeah, this is it,’” he said of those sessions. The team approach helped produce songs that caught wider attention.

One of those tracks, produced with the group, became his first Billboard credit. Wintons worked on a song titled “Loner” by rapper Boston Richey that later appeared on the Billboard 200, earning him his first chart plaque.

“You just go to the studio and cook,” he said. “Sometimes it happens kind of fast. He posted a snippet online and a week later it was out there.”

His studio work led to higher-profile collaborations and live dates, including serving as Music Director with rap artist Yung Bleu while on tour and recording sessions with artists such as Nardo Wick, Sada Baby and Melvin Crispell III.

Wintons recalled an early studio moment with Nardo Wick — who initially thought Wintons was the studio manager — when Nardo discovered he plays keys and asked him to teach a song ahead of a Rolling Loud performance.

He also spent time away from music, playing football at Alabama State, before returning to Jacksonville and committing to music full-time.

“College was dope,” he said. “I met so many different musicians. It opened my eyes.”

‘You gotta go learn’: Maintaining a signature sound

To stay relevant while keeping his signature sound, Wintons studies widely. He urged young musicians to learn multiple genres, perform in cover bands and absorb the feel of different musical traditions.

“Whether it’s rock, pop, jazz, hip-hop, EDM, house, everything has its true essence,” he said. “You gotta go and learn from those people who make that music.”

For those trying to break into music locally, his advice was practical: balance skill with personality.

“You don’t want to just be skillful and nobody wants to work with you,” he said. “But you also don’t want to be so cool and not really know what you’re doing. Have a balance of skill and personality.”

He emphasized preparation and professionalism. Being “a good steward” of his craft, he said, means showing up ready and exceeding expectations.

“When someone [calls] me for a session, I try to be super prepared, like overly prepared,” he said.

On stage, Wintons said the payoff is immediate. Live performance demands the rehearsal and musicianship that studio work builds, and crowd energy fuels improvisation.

“Playing live is all I did before studio,” he said. “It’s all in real time. You can’t go back and change anything.”

Behind the Board, I am...

“Passionate,” he said. “That’s the best way I can explain it, that’s where the passion comes out.”

Bob on Keys continues to produce, perform and travel while staying rooted in the musical lessons of his family and church. He said his goal is simple: make music that serves its purpose — to make people dance, cry or worship — and to reach the listeners it was meant to reach.

“When we hear a song, it automatically makes you feel a certain way,” he said.