Gimme Five

Sixteen years ago, Wednesday evenings in August weren’t so musical downtown. Thankfully, all that changed fifteen summers ago, when the Jazz at Five series began.

Executive director Cathy Sullivan remembers a group of downtown business owners, city officials and local musicians coming together to start a musical event that would fill the gap left after Concerts on the Square wrapped its season.


Jazz at Five started without a formal stage; essentially performers offered concerts for roughly one hundred people seated on folding chairs, Sullivan recalls.

“It was very small, very grassroots, very informal.”

Today, the event attracts two- to three-thousand people and features food vendors, a beer tent and reserved tables near a stage, set at the intersection of State Street and the Capitol Square.

"It’s evolved over the years,” Sullivan says.

Each Wednesday, Jazz at Five features two sets running 5–6:15 p.m. and 6:30–8 p.m. The series always incorporates local, regional and national acts, Sullivan says. And this year is no exception.


Chicago jazz quartet BMR4 and West Coast vocalist-pianist pair Nancy King & Steve Christofferson kicked off the 2008 season on August 6. The August 20 concert will serve as the fifteenth-anniversary celebration.

And Sullivan is excited to bring nationally known Afro-Cuban pianist Chuchito Valdés to Madison August 27, and vocalist Jon Hendricks on September 3. “He’s like jazz royalty,” she says.

Yet, Sullivan thinks all the concerts are stellar this year. “The schedule is all pretty great,” Sullivan says. “We have a lot to look forward to.”


Here’s the lineup for the rest of the Jazz at Five season:

August 13

Scott Burns Quartet This Chicago saxophonist and jazz quartet play original compositions by Burns as well as carefully selected standards.

Madison Jazz Orchestra Formed in 1986, this swinging jazz orchestra has played extensively throughout Madison and beyond, including Jazz at Five. Sax, trombone, tuba, trumpet, clarinet, guitar, bass, piano and drums are just some of the sounds you’ll hear from this group.

August 20

Gerri DiMaggio & Friends This Madison native—who’s been a guest artist with both the Madison Symphony Orchestra and Wisconsin Chamber Orchestra—offers an original sound, mixing Brazilian music with jazz standards.

Madison–New York Groove Collective This collection of jazz legends and artists with Madison and New York connections features Ben Sidran and Leo Sidran with guests Jay Collins, Moses Patrou and Amy Helm.

August 27

Alison Margaret Quartet A grad student in collaborative piano performance at UW–Madison, Margaret and her quartet specialize in innovative arrangements of American jazz and folk classics, plus lesser-known jazz tunes.

Chuchito Valdés Continuing the legacy of great piano players from Cuba, Valdés draws inspiration from Caribbean, Afro-Cuban Latin jazz, be-bop, Danzon, cha-cha-cha, Son Montuno and other styles.

September 3

Caravan Gypsy Swing This Madison-based instrumental group is inspired by Gypsy guitarist Django Reinhardt and finds influences in jazz, swing, traditional Latin, Parisian waltzes and other vintage-jazz sources.

Jon Hendricks & Company Jazz vocalist Hendricks is regarded as the “Father of Vocalese,” the art of setting lyrics to recorded jazz instrumental standards and arranging voices to sing the parts of the instruments.


Thanks to Mark Barrett of Steinway Piano Gallery for photos of the August 6 concert.