On Thursday night, seven-time Grammy award winner Al Jarreau opened up the festival as the evening’s headliner. Jarreau has conquered the genres of pop and R&B, as well as jazz. 

Chris Botti, jazz trumpeter extraordinaire and one of People Magazine’s 50 most beautiful people of 2004, headlined Friday night. “This applause makes all that travel and lack of sleep worth it,” Botti said of his warm Clearwater reception. Botti brought special guests singer Sy Smith and violinist Lucia Micarell to perform with him and his band.

The most moving moment of his set was his performance with Micarell. She had recently sustained a bad injury to her hand during a fall, while playing at a wedding in Italy. After four months of rehabilitation and not knowing if she could ever play again, Friday’s stirring performance marked Micarell’s triumphant return. “I know you’re crying. I’m crying,” said Botti after the song.

Saturday night’s concert featured the Extreme Tribute to the 30 years of Free Jazz in Clearwater. It was only fitting that thirty Clearwater Jazz Holiday Alumni – all Tampa Bay Home Grown – warmed up the audience with a variety of saxophone, clarinet, trumpet, keyboards, classical piano and vocals.

Perhaps most impressive was 17 year old BK Jackson on saxophone, who literally brought the crowd to their feet in a standing ovation. The Tampa native has recently graduated from Blake High School with a 5.1 GPA. Jackson has been playing since he was 11, and opened for Tony Bennett at last year’s Clearwater Jazz Holiday.

"It may be a little cool in the air but the jazz is still hot", praised Mayor Hibbard.

By the end of the evening some 17,000 jazz-hungry fans were satiated by smooth jazz saxophonist Boney James, a two-time Grammy nominee and a Soul Train Award winner, followed by a fireworks display sponsored by Homeowner’s Choice Insurance.

The four day event closed with a performance by the Neville Brothers on Sunday night. The recently reunited family act not only closed the festival, but closed out their performances for the year. After one more concert in New Orleans, the Neville brothers will have ended their live performance schedule for 2009.

The Clearwater Jazz Holiday has been an annual event for thirty years, with an attendant multitude of interesting stories attached to its name, including its first concert from the back of a flatbed truck. However, perhaps the most amazing thing about the Clearwater Jazz Holiday is that it has managed to stay free-of-charge for three decades, while bringing top talent to the festival and putting on such a high quality production. 

The event is funded through sponsorships, grants, and donations from jazz enthusiasts and concert goers. All the labor that goes into it is provided by “countless hours throughout the year with an all volunteer staff, the Jazz Force, comprised of a team of 60-plus along with over 1200 volunteers for the event itself,” says Gary Hallas of the Clearwater Jazz Holiday Foundation Board. “The Clearwater Jazz Holiday is one of the signature events for the City of Clearwater and our community,” he adds. “It is wonderful to be able to provide this quality of music for free – and we appreciate the support of the community through donations.”

This year also saw the return of the Jazz ’N Art Walk, an extension of the Clearwater Jazz Holiday on Cleveland Street. The outdoor art show and street festival was even larger this year, in size and success.

“It’s another great year,” said Mayor Hibbard. “Not many things are great after 30 years, but Clearwater Jazz Holiday is only getting better. We are looking forward to the 31st!”