CLEARWATER — Don’t let the name fool you.

Although the city’s signature event may have been created to showcase jazz musicians, since its inception it has evolved. These days, festivalgoers can expect to see and hear performances by a diverse cross section of musical artists.

HCI Group Inc. will present the 40th annual Clearwater Jazz Holiday, running Thursday through Sunday, Oct. 17-20, at Coachman Park, 301 Drew St., Clearwater.

Tickets start at $20 in advance. Children age 12 and younger are free. Limited reserved seating and VIP tickets are also available. For information, call 727-461-5200 or visit ClearwaterJazz.com or facebook.com/ClearwaterJazz.

Festival headliners this year include Boyz II Men on Thursday; Trombone Shorty & Orleans Avenue on Friday; Blood, Sweat & Tears and Chicago on Saturday; and Alison Krauss on Sunday. Fireworks will be presented Saturday at 10:45 p.m.

The annual event has come a long way from its humble beginning. In the early days, it took the form of a series of concerts on the back of a flatbed truck at venues around Clearwater. Over the decades, the festival has welcomed a long and impressive list of legendary jazz talents such as Woody Herman, Buddy Rich, Dizzy Gillespie, Herbie Mann, Dave Brubeck, Tito Puente, Stephan Grappelli, Stan Getz, and the Count Basie Orchestra. In recent years, the Clearwater Jazz Holiday has embraced a more diverse lineup, scheduling an array of performers skilled in many different musical styles such as straight ahead and smooth jazz, swing, blues, jamband, rock, folk, Americana, funk, and zydeco.

This year’s lineup continues that trend. Following is a look at this year’s performance schedule:

Thursday, Oct. 17

Gates open at 3:30 p.m.

• 3:45 to 4:45 p.m. — Jazmin Ghent

• 5:15 to 6:15 p.m. — Polyrhythmics

• 6:45 to 8 p.m. — The Soul Rebels

• 8:30 to 10 p.m. — Boyz II Men

Friday, Oct. 18

Gates open at 4 p.m.

• 4:15 to 5:15 p.m. — Gloria West and the Gents

• 5:45 to 7 p.m. — Marcia Ball

• 7:30 to 9 p.m. — Robert Randolph and the Family Band

• 9:30 to 11 p.m. — Trombone Shorty & Orleans Avenue

Saturday, Oct. 19

Gates open at 1:45 p.m.

• 2:15 to 3:15 p.m. — CJH’s Young Lions Jazz Master Sessions featuring James Suggs

• 3:45 to 4:45 p.m. — University of Miami's Frost Jazz Ensemble featuring Dafnis Prieto

• 5:15 to 6:45 p.m. — 40th anniversary tribute to jazz vocalists featuring Karen Benjey, Erica Diceglie, Valerie Gillespie, Fred Johnson, Theo Valentin, Belinda Womack and La Lucha

• 7:15 to 8:45 p.m. — Blood, Sweat & Tears

• 9:15 to 10:45 p.m. — Chicago

HCA West Florida will present fireworks at 10:45 p.m.

Sunday, Oct. 20

Gates open at 1:15 p.m.

• 1:30 to 2:45 p.m. — REH/CJH Youth Jazz Band with special guest Dafnis Prieto

• 3:15 to 4:15 p.m. — Ashley Smith & The Random Occurrence

• 4:45 to 6 p.m. — Parsonsfield

• 6:30 to 8 p.m. — Yonder Mountain String Band

• 8:30 to 10 p.m. — Alison Krauss

This year’s headliners

Boyz II Men take the stage Thursday at 8:30 p.m.

The American R&B and hip-hop vocal group got its start in the late 1980s in Philadelphia. Best known for emotional ballads and a cappella harmonies, they found fame in the 1990s with two Top 5 singles, including "Motownphilly" and "It's So Hard to Say Goodbye to Yesterday" in 1991. These were followed by the No. 1 single "End of the Road" in 1992.

Today, Boyz II Men remains an iconic R&B powerhouse. During their career, they’ve earned four Grammy Awards, nine American Music Awards, nine Soul Train Awards and three Billboard Awards. The trio holds the distinction of being the best-selling R&B group of all time, with 64 million albums sold.

Trombone Shorty & Orleans Avenue perform Friday at 9:30 p.m.

Troy “Trombone Shorty” Andrews is the bandleader and front man of this hard-edged funk band that employs brass-band beats, rock dynamics and improvisation in a jazz tradition. Andrews got his name when he picked up his instrument at the tender age of 4.

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Trombone Shorty

"My parents pushed me toward trombone because they didn't need another trumpet player," Andrews said in a press release from Universal Music. By 8, he was leading his own band in parades, halls and even bars. During his teenage years, Andrews played shows abroad with the Neville Brothers. Fresh out of high school in New Orleans, he joined Lenny Kravitz' band.

In 2010, Trombone Shorty's album “Backatown” was nominated for the Grammy Award for Best Contemporary Jazz Album. In 2017, he teamed up with Grammy-nominated producer Chris Seefried for his Blue Note Records debut “Parking Lot Symphony.” The album contains multitudes of sound — from brass band blare and deep-groove funk, to bluesy beauty and hip-hop/pop swagger — and plenty of emotion all anchored by stellar playing and the idea that, even in the toughest of times, as Andrews says, "music brings unity."

Blood, Sweat & Tears plays Saturday at 7:15 p.m.

This jazz-rock Canadian-American music group literally invented a new style of music. Flash back in time to 1967 when the founding members — including Al Kooper, Jim Fielder, Fred Lipsius, Randy Brecker, Jerry Weiss, Dick Halligan, Steve Katz and Bobby Colomby — were practicing in a loft on Bleeker Street in New York’s Greenwich Village. The music started attracting crowds in the street below. In the years that followed, the band introduced a combination of brass and rock band instrumentation, fusing rock, jazz and blues. While their debut album didn’t attract much attention, their sophomore effort became a success, rising to the top of the charts for seven weeks and yielding five singles. The album earned the Grammy Award for Album of the Year in 1970, beating out the Beatles’ "Abbey Road."

Chicago takes the stage Saturday at 9:15 p.m.

Calling themselves the “rock and roll band with horns,” Chicago — known originally as “Chicago Transit Authority” — formed in 1967 in the Windy City. Blending elements of classical music, jazz, R&B and pop music, they released their first album in 1969. “Chicago XXXVII: Chicago Christmas,” the band’s 37th album, is due out this month. Chicago is the first American band to chart Top 40 albums in six consecutive decades.

Chicago’s lifetime achievements include two Grammy Awards, two American Music Awards, Founding Artists of the John F. Kennedy Center for the Performing Arts and a star on the Hollywood Walk of Fame. Their record sales top the 100 million mark, and include 21 Top 10 singles, five consecutive No. 1 albums, 11 No. 1 singles and five gold singles. An incredible 25 of their 36 albums have been certified platinum, and the band has a total of 47 gold and platinum awards.

Among Chicago’s hits are songs such as “25 or 6 to 4,” “Saturday in the Park,” “Feelin’ Stronger Every Day,” “If You Leave Me Now,” “Hard to Say I’m Sorry,” “Hard Habit to Break,” “I’m a Man” and “You’re the Inspiration.”

Alison Krauss closes out the Clearwater Jazz Holiday, performing Sunday at 8:30 p.m.

The bluegrass-country singer and musician got an early start in the music industry, playing on “Different Strokes” with her brother Viktor Krauss when she was just 14. She signed with Rounder Records that year, and in 1987 she released “Too Late to Cry.”

According to a biography provided by Press Here, part of Krauss’ incontestable talent is how effortlessly she bridges the gap between roots music and country, rock and pop. A highly sought-after collaborator, Krauss has worked with some of the biggest names in popular music, including James Taylor, Phish, Dolly Parton, Yo Yo Ma & Bonnie Raitt. Since signing with Rounder Records, Krauss has sold in excess of 12 million albums. Her recent 27th Grammy win makes her the most awarded female artist, most awarded singer and tied for second for most awarded overall in Grammy history.

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Alison Krauss

In 2017, Krauss released “Windy City,” her fifth solo studio album. It is her first effort away from her band Union Station since “Raising Sand” and her debut for Capitol Records. The album features Alison performing 10 classic songs that she carefully selected with producer Buddy Cannon. What she and Cannon have created is an album suffused with sadness that somehow rarely sounds that way.

“It’s almost like you didn’t know it was sad, because it doesn’t sound weak,” Krauss said on her Facebook page. “It doesn’t have a pitiful part to it, where so many sad songs do. But these don’t. And I love that about it. I love that there’s strength underneath there. That whatever those stories are, they didn’t destroy. That that person made it right through it. I love that.”

Festival highlights

Jazmin Ghent kicks off this year’s Clearwater Jazz Holiday, taking the stage Thursday at 3:45 p.m.

Born in Germany, Ghent currently resides in Central Florida. She earned a bachelor’s degree from Florida State University and a master’s degree from Tennessee State University.

“Boss,” her debut album, was released in June 2015. She released a follow-up, “Chocolate Sunshine,” in 2016. “The Story of Jaz,” her 2018 album, features collaborations with Phillippe Saisse, Kim Scott, James Lloyd and Jeff Lorber. The CD was recorded and produced by Ron Jenkins and Euge Groove at “The Groove House.”

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Jazmin Ghent

“The Story of Jaz” earned Ghent the prestigious 2019 NAACP Image Award for Outstanding Jazz Album.

In addition to performing, Ghent teaches music in Polk County to elementary students in grades K-5.

Gloria West and the Gents perform Friday at 4:15 p.m.

The acclaimed group has been performing throughout the Tampa Bay area since 2014, and has been described as “pure, tight, sensual artistry.” Gloria West and The Gents perform originals with West delivering vocals reminiscent of Lady Day. They deliver originals, pop covers, favorites from the 1920s, 1930s, and 1940s, and even old-time movie classics and Disney songs, all with an old jazz feel. West has been compared to Norah Jones and Billie Holiday with the lighthearted fun of “Mrs. Swing” Mildred Bailey added in.

Her mission is to create and share “jazz for the masses” and to spread her love of jazz to everyone. That includes introducing new audiences to jazz who have little knowledge of it, and even bringing others around that don’t know about its amazing roots and thought they didn’t like the genre.

“I want to create jazz in an accessible way where everyone can understand and appreciate its broad appeal,” West said in a press release.

Gloria West and The Gents released their debut album “Dem Keys” on CD in 2017 to rave local reviews. In December 2018, they released it as a deluxe edition with three bonus songs on a collector’s edition red vinyl record as well as digital download. It is also available on major platforms for streaming and downloading and is currently making its way around the world. The project was fully fan-funded and recorded locally with top-notch local musicians and is comprised of original songs as well as old jazz and pop covers with their distinct vintage spin.

“We were actually lucky enough to have played the Clearwater Jazz Holiday in 2015,” West said in an email. The band had had only been around for a year and a half at that point. “It was extra-exciting business.”

The band learned they’d been added to the 2019 lineup a few months ago and they’ve been preparing ever since.

West said she cut her teeth on artists such as Norah Jones growing up. She names Harry Connick Jr. as a significant influence, particularly in the way she presents herself on stage.

“He's one of my oldest influences, and it was funny to see him for the first time and see so many things that he did that I had already planned to add to some of my bigger shows,” West explained. “Great minds think alike, I guess.”

Marcia Ball performs Friday at 5:45 p.m.

Ball has won worldwide fame and countless fans for her ability to ignite a full-scale roadhouse rhythm and blues party every time she takes the stage. Ball’s rollicking Texas boogies, swampy New Orleans ballads and groove-laden Gulf Coast blues have made her a one-of-a-kind favorite with music lovers all over the world. “Shine Bright,” produced by Steve Berlin of Los Lobos, is full of everything music fans love about Ball – rollicking two-fisted piano, soulful vocals, a top-shelf band of Texas and Louisiana musicians, and magnificent songwriting. In October 2018, Ball was inducted into the Austin City Limits Hall of Fame.

Marcia Ball

Marcia Ball

With “Shine Bright,” Ball set out to, in her words, “make the best Marcia Ball record I could make.” In doing so, she has put together the most musically substantial, hopeful and uplifting set of songs of her five-decade career. Recorded in Texas and Louisiana, “Shine Bright” contains 12 songs – including nine originals – ranging from the title track’s rousing appeal for public and private acts of courage to the upbeat call to action of “Pots and Pans,” a song inspired by renowned Texas political writer and humorist Molly Ivins. From the humorous advice of “Life of the Party” to the poignantly optimistic “World Full of Love,” the intensity of Ball’s conviction never wavers while, simultaneously, the fun never stops. “Shine Bright” is exactly the album Ball set out to make.

“It is a ridiculously hopeful, cheerful record,” she said in a press release from Alligator Records. Though the album boasts some serious subject matter, the secret, according to Ball “is to set the political songs to a good dance beat.”

Born in Orange, Texas in 1949 to a family whose female members all played piano, Ball grew up in the small town of Vinton, Louisiana. Seeing an Irma Thomas performance in 1962 and falling under the spell of Professor Longhair’s piano playing convinced Ball to seek out a career in music. She led a couple of early psychedelic country rock bands before pursuing her solo career from her adopted hometown of Austin, Texas.

Yonder Mountain String Band plays Sunday at 6:30 p.m.

For the past 20 years, Yonder Mountain String Band has redefined bluegrass music, expanding the traditional acoustic genre beyond its previously established boundaries by steadily pushing the envelope into the realms of rock n’ roll and improvisation. YMSB features guitarist Adam Aijala, bassist Dave Johnston, banjo player Ben Kaufmann, Jacob Joliff on mandolin and violinist Allie Kral. The band has always played music of their own design, in the process attracting a devout following of fans that often resembles a tight-knit family on an epic musical journey.

YMSB is a quintessential ensemble honing its craft night after night on the road, and the fans are there to experience it in real time. The result is music that doesn’t stand still, it’s always progressing and breaking unprecedented ground.

Safety and security

A number of safety and security measures have been put in place at the Clearwater Jazz Holiday. Several items and practices will not be permitted at the event, including pets, except registered seeing-eye dogs and service dogs; grills, hibachis or open flames of any kind; glass containers or bottles; coolers, food or drink of any kind; unauthorized vendors; tents, canopies or umbrellas; overnight camping; audio and/or recording devices; in-line skating and skateboarding; littering; guns, unless otherwise permitted by Florida Statute, Chapter 790; knives or weapons of any kind; cell phones or pagers during performances; fireworks; and laser pointers.

Concertgoers should attend all infants and small children. Attendees are encouraged to bring lawn chairs, blankets, sunglasses, sunscreen and identification tags for small children.

For more information, visit www.clearwaterjazz.com or call Clearwater Jazz Holiday office at 461-5200.

Clearwater Jazz Holiday After Party

The Clearwater Jazz Holiday After Party will take place Friday, Oct. 18, 10:30 p.m., at the Nancy and David Bilheimer Capitol Theatre, 405 Cleveland St., Clearwater.

Tickets are $21 in advance. Call 727-791-7400 or visit www.rutheckerdhall.com.

Allon Sams will host the event, which will feature a performance by the Clearwater Jazz Holiday Jam Band. Cocktails and concessions will be available for purchase.