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Jerry Grillo has been at it long enough to call himself a veteran—even if he answered his calling as a jazz singer relatively late in life. Only after retiring from a career as a schoolteacher in 1992 was Grillo able to devote himself to his first love. Since then he has released no fewer than nine CDs. He has also watched CD sales shrink, the ladders for getting a leg up in the industry collapse and opportunities to perform dwindle.

“People say, ‘I got your CD at the library and copied it!’ How am I supposed to answer that?” Grillo says with a sigh. “For singers, it’s not as good as it was.”

Grillo forges onward anyway, lending his foggy voice to the standards of pre-rock American songs in settings that sometimes depart from the norm. He’s enjoyed a varied track record, performing with a diverse range of musicians, including The Danglers and the Nick Contorno Orchestra. He’s sung with only a pianist for accompaniment and with a trio. Usually his combo includes bassist Madeline Dietrich, guitarist Kirk Tatnall and percussionist Randy Maio, who loves slapping the skins with his palms and playing with wind chimes as well as drumsticks.

To find work in restaurants and private functions, many jazz singers have switched to pop tunes, “and not in a jazz way,” Grillo adds. He has always sung a few of his favorites from the 1950s (“Venus”) and has added a couple of country songs (“For the Good Times,” “Rambling Rose”) that open easily to jazz, but prefers to draw from the classic jazz singer repertoire. Songs popularized by Frank Sinatra are a mainstay, along with compositions by Antonio Carlos Jobim for a Brazilian lilt, a funky “Summertime” and a sizzling, edgy rendition of “Fever.”

“I can’t change ‘Moonlight in Vermont’ or ‘The Nearness of You’ in good conscience,” he says. “But we do many songs in a nontraditional way, changing the chords, the voicings and the rhythm. Kirk will play guitar with pedals and come close to a rock guitar solo—never a real rock solo, but close.”

Grillo’s voice has gained assurance and nuance, as attested by a close listen to his 2009 anthology CD, Some of the Best. He pops up in unexpected venues, such as LuLu Café or Paddy’s Pub, and accepts the changing times with a shrug. “I wonder sometimes if I shouldn’t have left town, but the problem is I really love Milwaukee. Where else would I have gotten an award? I’m proud of my WAMI.”

Jerry Grillo performs 10 p.m. March 31 at Transfer, 101 W. Mitchell St.

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