Jerry Grillo was a little taken aback. When a fan he had never met before, Lisa Chiappetta, showed him the video she made on her cell phone camera of one of his performances, Grillo thought, “I don’t like the YouTube quality.” But the encounter sparked a series of conversations, a train of thought that led to the Milwaukee jazz singer’s latest project.

Starting this spring, the Jerry Grillo Historical Mystery Band will be on a tour of landmark local venues, trailed by cameras. Lisa’s husband, Tim Chiappetta of Milwaukee Metro Design, will edit the footage into a documentary suitable for the festival circuit.

“I thought it would be fun to do something more involved and of better quality than just something you throw online,” Grillo says.

The singer and showman is no stranger to working with film and video artists. In the early ’90s, when his career as an interpreter of classic songs had just begun, Grillo did a short subject with Milwaukee filmmaker Cathy Cook, who has since gone on to national acclaim. The intervening years, however, mostly have been devoted to making music. Grillo has released no less than eight CDs and recently posted an original song on his website.

Music will be the most significant aspect of the planned documentary, but not the only one. “To me, it’s a historical journey,” Grillo explains. “I’m picking venues that don’t normally feature jazz, located in buildings associated with Milwaukee history in some way.”

He chose the location for this weekend’s gig at Café LuLu (2265 S. Howell Ave.) because the building once housed one of those favorite diners for Milwaukee night owls, George Webb. On May 13, Grillo will take the show to the Harbor Room (117 E. Greenfield Ave.).

The Historical Mystery Band features top-flight local jazz musicians, including Kirk Tatnall on guitar and bass, Scott Currier on keyboards, Mike Caldwell on saxophone and Randy Maio on drums and all manner of percussion. Several songs in the set list are instrumentals by Tatnall and Currier, but the focus will be on songs chosen and sung by Grillo.

“I don’t go beyond the ’60s—it’s hard to find songs that are good for me from beyond the ’60s,” he says, explaining a repertoire that runs roughly from Gershwin through Lennon and McCartney. Although in earlier years he was a purist, Grillo has become a creative interpreter. “I wanted to appeal to a different audience and create something more exciting for the band as well,” he says, explaining the reggae rendition of “Witchcraft” and an “almost hip-hop” take on “Summertime.”

The Jerry Grillo Historical Mystery Band performs at 10:30 p.m. Saturday, May 8, at Café LuLu.