Jerry Grillo Counts Down the Decades

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Jerry Grillo made the best use of his early retirement. After ending his career as an MPS teacher, he focused on his first love. He’d sung in musical theater after school, and with a cover band, Sweet Earth, but with his career behind him, Grillo had time to study the craft of jazz vocals. He found opportunities to entertain at jazz clubs and piano bars and just enough success to sustain a prolific sequence of half a dozen albums released from the ‘90s through the ‘00s.

He also wrote and recorded a song, “My Hometown Milwaukee,” in the manner of Frank Sinatra’s “Chicago.” Mayor Cavalier Johnson proclaimed May 13, 2022, as “My Hometown Milwaukee Day” and presented Grillo with a plaque at City Hall.

And Grillo isn’t done yet. Late last year, he launched what he calls his “Decades Tour” at Bar Centro. “If Taylor Swift can do an Eras Tour, I can do a Decades Tour,” he explained. He sang at the Estate on Dec. 23 (tickets sold out in advance) and will perform at bar centro, 8 p.m. Feb 10. More shows are in the works for 2024.

For the Decades Tour, Grillo assembled a two-hour show (with intermission) that surveys the varied repertoire he performed over the years from musicals to big band and jazz standards. “I am getting the most applause I’ve ever gotten,” he said. “The Broadway stuff seems to suit me well, and I’m doing lots of Tony Bennett songs.”

Grillo composed short introductions for each number, framing the concerts as a personal musical history tour. Before singing “The Trolley Song” from Meet Me in St. Louis, Grill recalls his long-ago meeting with Judy Garland. “On a Clear Day” gives rise to his reflections on the influence of Barbra Streisand’s voice. The Decades Tour also includes numbers from Company, Fiddler on the Roof and Cabaret that Grillo sang in the ‘70s with the Milwaukee Players.

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In a recent press release, Grillo declared, “I do believe that this is near the end of what has been an amazing experience.” The statement sounded doleful, but he walked it back in a personal conversation. “It can’t go on forever,” he said. “The ‘end’ means to do a show that encapsulates the music of my life going from the late ‘60s through the 2010s. I’ve done different things along the way, and I want to showcase that.”