Jerry Grillo

Jerry Grillo

Jerry Grillo hasn’t achieved the level of fame enjoyed by Bob Dylan, his high school’s most famous alumnus. But like the Nobel Prize winner, Grillo accomplished what he set out to do when he left Hibbing, Minnesota, and he’s grateful for the career he made for himself after moving to Milwaukee in 1968.

That career, Grillo says, still is moving forward.

Starting out after college, Grillo was torn between his desire to teach and his dream of singing, and Milwaukee afforded him both opportunities. During his years at John Marshall High School, Grillo was free to perform on the weekends and to tour with his band in the summer, exposing him to a larger audience. His name never became a household word, but in addition to his local fan base, he developed followers through his performances on the road. 

Grillo put his music career on a back burner during much of his time with MPS, but he turned again to music as he approached retirement.

He’s released 10 recordings, beginning with 1992’s This Funny World, recorded in Chicago and produced by Jackie Allen, his mentor at the Wisconsin Conservatory of Music. The song “Lonely,” which Grillo co-wrote and recorded in 2005, made Billboard’s Top 100.

But “Stardust” is his favorite creation. He dedicated the recording of it to Karl Kopp, owner of Elsa’s on the Park. “He played everything I ever recorded, and whenever I visited the restaurant, he’d put on one of my songs,” Grillo says.

The Wisconsin Area Music Industry has recognized Grillo with four nominations for Jazz Artist of the Year, and he took home the prize in 2011. That was an unexpected honor, he says, because vocalists seldom win in the category.

Although he’s appeared at many venues in the Milwaukee area, Angelo’s Lounge and Piano Bar, 1686 N. Van Buren St., was Grillo’s musical home for several years.

“Angelo’s was a labor of love,” Grillo said. Owner Angelo Martellano was aging and needed help keeping the doors open. Grillo booked instrumentalists for Martellano and played a regular gig there Friday nights for several years. He struggled alongside his longtime friend, giving up other opportunities to help keep the business open.

“There was no way I would have left,” Grillo says. “Martellano had that business for 30 years. It was very sad to see that business go down.”

Martellano died in 2016. In collaboration with John Hefter, Grillo’s written two songs honoring him. They’re scheduled for release at the end of 2018.

These days, Grillo considers his home to be The Jazz Estate, 2423 N. Murray Ave., on Milwaukee’s East Side. It’s a small, unassuming place, but it’s famous in the jazz world. Luminaries such as Harry Connick Jr. go there to jam after their big shows downtown.

This year marks the 50th anniversary of the first time Grillo was paid for singing, as well as the 25th year that he’s performed at The Jazz Estate, where he has a celebratory gig set for Sept. 12.


Investing in schools

Grillo attributes his success in part to the exceptional high school he attended in his hometown.

Hibbing recognized its children as the world’s future leaders, and city leaders were determined to prepare them for that role. In 1920, Hibbing, with financial assistance from the local mining industry, built a $1 million (more than $13 million in today’s dollars) high school designed in Jacobean Revival architectural style, complete with marble and brass flourishes. The auditorium was particularly lavish, modeled after the Broadway theater palaces of its day, with chandeliers made from imported Belgian crystal.

Grillo and Dylan, who is three years Grillo’s senior, performed in musicals on that grand stage — experiences that illuminated their dreams of what was possible.

The purpose of giving students such a magical place to study was to make them feel valuable and gird them for success, says Grillo, who realized at a young age that he had a strong voice and studied opera.

For a town of 16,000 residents, Hibbing has produced a variety of successful people. The list includes baseball’s Roger Maris, basketball’s Kevin McHale and hockey player Joe Micheletti. Vincent Bugliosi, who prosecuted serial killer Charles Manson, gay porn director Chi Chi LaRue, world-renowned architect John P. Sheehy and winemaker Robert Mondavi also called Hibbing home.


Stylings and standards

Grillo focused on the pop standards that dominated the airwaves between World War II and the rock era. Enduringly popular, they were songs recorded by America’s legendary vocal stylists — Frank Sinatra, Tony Bennett, Jack Jones, Andy Williams, Nat King Cole, Vic Damone, Eydie Gormé, Steve Lawrence, Johnny Mathis, Lena Horne and dozens of others. Their music continues to thrive at weddings, bar mitzvahs and supper clubs, and it continues to chart today in contemporary interpretations by Barbra Streisand, Michael Bublé, Diana Krall and others.

Grillo was drawn especially to the musical styles of the era’s female stars, such as Dinah Washington and Sarah Vaughan — and especially to Ella Fitzgerald and Barbra Streisand. “Singing along with Barbra has kept my voice in shape,” he says.

The American standards lend themselves easily to jazz interpretations, and it’s at that nexus that Grillo is now focused. He considers himself, first and foremost, a jazz singer.

Today, he’s most inspired by Bennett. In recent years, like Bennett, he’s even taken up painting. A framed dollar bill that Bennett autographed for Grillo in a grocery store checkout line adorns one of his walls.


Punctuating with volume

Grillo often appears onstage in a less self-conscious version of a Rat Pack-styled jacket or suit and a narrow tie. Usually, he dons a fedora, and sometimes a scarf. The look is original and cool, evocative of a bygone era but not an imitation.

At 74, Grillo’s face looks lived in but not worn out. Onstage, he projects confidence and control. He has a tough, brooding look that could get him cast in Hollywood as a Mafia boss.

Although Grillo can come off as the kind of guy you don’t want to mess with, he also seems like someone you’d want to tell your troubles to.

His voice can go big, but in performance, he saves volume to create dramatic moments. He writes poetry — most recently “Hiding Places,” which addresses bullying — and, in singing, he uses volume like a writer uses punctuation.

His performing style often seems like storytelling. He cups the microphone in an intimate way, as if he’s sharing a secret. Sometimes, he holds the microphone with one hand and uses the other in an almost-conversational manner. 

“To me (singing) is like poetry being interpreted lyrically,” he says.

Over the years, Grillo’s voice has taken on a gravelly quality that works well for him. It’s an appealing development that’s brought him new attention, and he plans on developing and using it to give his career a new kick. He’s nowhere near putting down the microphone.

“I have a suspicion that something still might happen,” he says.

But for decades of fans who’ve been enlivened by Grillo’s jazz and been moved by his sentimental crooning, Grillo is still happening — and always will be.

Jerry Grillo performs at the Jazz Estate, 2423 N. Murray Ave., on Sept. 12. Call 414-964-9923 or visit the calendar at 


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