Changing Tunes: Five O'Clock Club's new image

George Generoso has found what he was looking for. He emerges from a storage closet carrying a box of old photos he plans to have digitized later in the week.

He flips through the pile of dusty laminated pictures, smiling as he remembers some of the more noteworthy acts that have played at the Five O’Clock Club in the 20 years he’s been co-owner.

Dozens of reputable musicians are represented in the pile — R.L. Burnside, The Allman Brothers, Buddy Miles — but Generoso no longer displays them on the wall above the bar. And not just because the bass from live shows kept knocking them down. He says he’s ready to embrace a new image for the bar.

“Music grows and evolves. Hip-hop is a huge part of our culture, and it has been for a long time. To pretend like it’s not is old-fashioned.” — George Generoso, co-owner, Five O’Clock Club.

Known primarily as a blues club, the Five O’Clock Club will celebrate its 60th anniversary this Saturday with something its regulars might not expect: its first ever hip-hop show.

“This is a music venue,” says Generoso. “And I enjoy all types of music. There’s a whole demographic of younger music fans in Sarasota, who grew up with a completely different appreciation for music. I want to reach those people, too.”

When Generoso first took over as co-owner in 1995, the club was hosting almost exclusively blues musicians. Wanting to appeal to a wider audience, he began incorporating other genres, including rock, grunge and reggae, and he began to see a lot of new faces. Now, he says it’s time to adapt again.

Feeling that Sarasota’s millennial audience was underserved, Generoso decided to partner with local hip-hop artist Ryan Larranaga, who performs as Ryanito, to appeal to a younger crowd. For the last few weeks, Larranaga has hosted late-night DJ performances at the bar in a series called “DJs After Dark,” and Generoso says they have a shared vision for Sarasota’s music scene.

When considering options for Halloween and the bar’s 60th anniversary celebration, Generoso reached out to Larranaga to put together something unique.

“I’m always looking for ways to integrate hip-hop into Sarasota’s mainstream culture,” says Larranaga. “I’ve always been a fan of the Five O’Clock Club. It’s a place where I go to discover new musicians, and I thought, ‘Why not have hip-hop there, too?’”

Larranaga assembled a lineup that includes himself, three other performers and two DJs. He says the acts range in style from hip-hop to R&B, and that there will be something that everyone can enjoy. Most importantly, though, he says the show is about spreading positivity.

“Every act on this bill has a socially conscious message,” he says. “A lot of people associate rap with violence and negativity, but we want to show people the activist portion of the genre.”

That mindset is part of what inspired Generoso to first work with Larranaga.

“I like what Ryan’s doing,” he says. “I like the message he’s trying to put out there. Of course, there are traditionalists who are set in their ways. But that’s what they said about rock and jazz — it’s the devil’s music. It’s all just music. I want this club to grow and change with the times.”

Larranaga says he's looking forward to introducing his music and hip-hop culture to the historic venue.

"It's a perfect fit," he says. “It’s got the right intimate vibe. When you pack the place, there’s so much energy. If you’re not a fan of hip-hop, you will be by the time you leave.”