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Clearwater Jazz Holiday at 40: A look at its past, present and future

The annual event, which returns this weekend, has come a long way. Where will it go from here?

You know who we all ought to thank for the Clearwater Jazz Holiday? European tourists.

“We had lots and lots of Europeans that vacationed in Florida and Clearwater,” said Cary Stiff, one of the co-founders of the annual festival. “And jazz, for Europeans, was a big deal. It was relatively noncontroversial, it was on the quiet side, it had people come down to enjoy the waterfront. It was beautiful."

All those visitors from Lisbon and Liverpool and Leipzig couldn’t have known it back in 1980. But they helped inspire what has become one of Tampa Bay’s signature annual festivals, which celebrates its 40th edition this weekend.

Over four decades, the Clearwater Jazz Holiday has evolved from a loose slate of concerts organized through the local Chamber of Commerce to a premiere festival that encompasses a lot more than jazz. The event has hosted everyone from Tony Bennett to Tito Puente, Chick Corea to Kenny G, Etta James to the Avett Brothers, all while weathering industry changes that have forced other festivals to buckle and crumble.

“It’s definitely a milestone we are proud of,” said Steve Weinberger, CEO of the Clearwater Jazz Holiday Foundation. “This year’s festival will be an emotional four days, but in a great way, as we celebrate generations of volunteers that have contributed along the way.”

To stay relevant over 40 years, the festival has had to strike a tricky balance. They’ve had to figure out how to afford bigger-name talent without driving away fans who, until the fest began charging for tickets in 2012, expected always to get in for free. They’ve had to lure in new patrons without alienating jazz traditionalists screaming PLEASE JUST LET US HAVE THIS ONE THING.

So what does this year’s Clearwater Jazz Holiday look like? How does it stack up to the festival’s first 40 years? And where will it go in the next 40? Here’s a little food for thought.

From left, Nick Lane (trombone), Walter Parazaider (saxophone) and Lee Loughnane (trumpet) performed with Chicago at the 34th annual Clearwater Jazz Holiday on Oct. 17, 2013, in Coachman Park. [DOUGLAS R. CLIFFORD | Tampa Bay Times]

Who are this year’s headliners?

Thursday night starts hot and heavy with Boyz II Men (8:30 p.m.) doing a little East Coast swing, melting early-'90s hearts with R&B hits like End of the Road, It’s So Hard to Say Goodbye to Yesterday and I’ll Make Love to You. They’ll be joined by hip-hop-inspired New Orleans brass ensemble the Soul Rebels (6:45 p.m.), and if there’s any justice in the world, they’ll join forces for a horned-up rendition of Motownphilly.

Friday brings festival favorite Trombone Shorty and Orleans Avenue (9:30 p.m.), making their fourth appearance in Clearwater this decade and first since 2016. Pedal steel kings Robert Randolph and the Family Band (7:30 p.m.) and veteran blues singer Marcia Ball (5:45 p.m.) are also on the bill, setting the stage for what could yield an electric jam session, if all parties are so inclined. There’s also an after-party at 10:30 p.m. at the Nancy and David Bilheimer Capitol Theatre with Allon Sams and more; tickets are $21 and up.

On Saturday, brass-happy Rock and Roll Hall of Famers Chicago (9:15 p.m.) will close things out for the first time since 2013, while the remnants of jazz-pop fusion Grammy winners Blood, Sweat and Tears (7:15 p.m.) will perform around sundown. After Chicago shuts it down with 25 or 6 to 4, look for fireworks at 10:45.

And on Sunday, 27-time Grammy winner Alison Krauss (8:30 p.m.) will make a rare local appearance headlining what has come to be known as the festival’s Americana day. A couple of other neo-folk acts, Yonder Mountain String Band (6:30 p.m.) and Parsonsfield (4:45 p.m.), join her.

Alison Krauss will perform at the Clearwater Jazz Holiday on Oct. 20. [Capitol Records]

But where’s the jazz?

Ah, yes, this old question. Every year, folks who remember the days of headliners like Dave Brubeck, Buddy Rich, Stan Getz and Dizzy Gillespie bemoan what the weekend has become: just another pop-rock festival that’s jazz in name only.

RELATED: 11 places to hear live jazz in Tampa Bay

When the Clearwater Jazz Holiday went pop and started charging for admission in 2012, it signaled organizers’ desire to evolve rather than die. (Maybe they weren’t wrong — just look at what happened with St. Petersburg’s venerable Ribfest, which ended this year after years of struggling to draw in younger fans.)

RELATED: Ribfest ending after 30 years in St. Petersburg

Look at all the other great festivals with “jazz” in the name. This year’s New Orleans Jazz and Heritage Festival offered Katy Perry and Pitbull. Switzerland’s Montreux Jazz Festival brought in Janelle Monae and Lizzo. The Montreal Jazz Festival featured Bryan Adams and Peter Frampton. In this context, a festival with Chicago and Trombone Shorty at the top looks right in line.

Dizzy Gillespie plays at the Clearwater Jazz Holiday in Coachman Park in 1982. [Tampa Bay Times]

That said, if you look beyond the headliners, there are jazz artists worth catching on this year’s bill.

Seattle’s Polyrhythmics (5:15 p.m. Thursday), an instrumental funk-fusion collective, have played a variety of jazz, jam and pop festivals. Cuban-American drummer Dafnis Prieto, a 2011 MacArthur “genius grant” winner and faculty member at the University of Miami’s Frost School of Music, will perform with different student ensembles at 3:45 p.m. Saturday and 1:30 p.m. Sunday.

And any fans pining for the good ol’ days of the Clearwater Jazz Holiday will want to stake out a good seat at 5:15 p.m. Saturday for a 40th anniversary tribute to jazz vocalists featuring a who’s who of the Tampa Bay jazz scene: Belinda Womack, Valerie Gillespie, Fred Johnson, Theo Valentin, La Lucha and more. Most have played multiple festivals “and are special to the tradition,” Weinberger said.

Fred Johnson opens the Clearwater Jazz Holiday on Oct. 13, 2005. [FLYNN, KATHLEEN | Tampa Bay Times]

After 40 years, what comes next?

Part of the answer may come when city leaders reach a final decision on a long-discussed downtown redevelopment plan, Imagine Clearwater, which is slated to include a permanent, 4,000-seat amphitheater in Coachman Park. If the venue ever gets built, it could boost attendance and help draw larger names.

“When they visit, things are going to look different, they’re going to feel different," said Stiff, who now sits on a committee for the festival’s long-term planning, and this year helped create an endowment for that purpose. "That’s what you need. It’s lasted this long, for 40 years, based on what it was. Now when you enhance it and give people more choices and more amenities, I think they’ll do fine.”

RELATED: Imagine Clearwater is taking shape. Here’s the latest on the $60 million-plus downtown waterfront.

One way to grow the festival’s audience without alienating (too many) traditionalists might be to put out feelers to younger, jazz-inspired talents from various genres. Artists like singer-songwriters Natalie Prass and Madison Cunningham; poetic neo-R&B talents Jamila Woods and NoName; or hip-hop-connected instrumentalists Robert Glasper, Terace Martin and Kamasi Washington. Heck, book an after-party with Flying Lotus, a hip, eclectic producer and DJ whose great-aunt was Alice Coltrane.

On the other hand, one could argue the Clearwater Jazz Holiday is already doing what it needs to do to ensure its long-term survival. While down from around 100,000 at its free peak, four-day attendance has generally grown since they instituted ticketed admission, from 28,000 in 2012 to 37,000 last year. That’s close to where it was in the years before ticketing.

While the holiday was developed in part with European tourists in mind, Stiff said it won’t be able to rely on its same old supporters forever.

“As musical tastes evolve, you have to evolve with that,” she said. "Because if us old folks begin to die off 15 or 20 years from now, you’re going to have to build the newer audiences.”

But when she returns to Coachman Park to help celebrate the 40th birthday of the festival she helped found, she believes she’ll see a bright future.

“I may be a proud parent, and I may be biased,” Stiff said, “but I will tell you, it still gives me the chills to see yourself standing on the Clearwater harbor, looking out of the water with the harvest moon and the StarLite Cruise ship going by. There just isn’t a better view than that in the whole world.”

An aerial view of the Clearwater Jazz Holiday on Oct. 22, 1995. [KEELER, SCOTT | Tampa Bay Times]


Tickets start at $20 per day, $35 for Saturday-Sunday and $70 for the weekend. Coachman Park, Clearwater. (727) 461-5200.