Last call: After 40 years in Madison, musician ‘Robert J.’ heads east

Robert J. Conaway — who goes by “Robert J.” in his career as a singer-songwriter — first saw Madison in the company of an old girlfriend. They were visiting her sister, who lived on Mifflin Street.

It was the weekend of the Mifflin Street Block Party, a rite of spring with beer in half barrels and musicians on stage.

“We had a grand time,” Conaway says. “I thought, ‘This is a cool town. Maybe I could do that.’ Two years later, I moved to Madison and I was on that stage.”

It was 1982.

This week — following one last Labor Day gig at Christy’s Landing on Monday, Sept. 6 at 2 p.m. with his band, The Moon Gypsies — Conaway will load a U-Haul and drive to Connecticut, joining his wife, Jill Conaway, who relocated in late June for a principal’s job at a Catholic school outside of Hartford. They’ll live in East Hampton.

Her career includes more than two decades in education administration in the Madison area.

“I said, ‘Go for it,’” Conaway says, when his wife learned of the Connecticut opportunity. “‘You’ve backed me all along. I’m there for you if that’s what you want to do.’”

And so marks the end of an era on the Madison music scene. Along with innumerable gigs across 39 years — solo, with The Moon Gypsies and with his country-rock band, The Rowdy Prairie Dogs — Conaway initiated a legendary Sunday jam session at Morgan’s on Atwood Avenue that regularly drew the city’s best musicians and ran for a decade — 518 Sundays.

In the life of a musician, each gig is a story, and few are better than the time in August 1996 when Conaway opened — solo — for The Beach Boys at the Dane County Coliseum.

“During the sound check,” Conaway says, “I broke into a slow version of ‘Do You Wanna Dance.’ Their road manager came running up from the sound board and said, ‘This is a Beach Boys concert! Beach Boys do Beach Boys songs! You don’t do their songs!’”

Conaway didn’t point out that “Do You Wanna Dance” is actually a Bobby Freeman song — Freeman wrote it and had a top 5 hit with it in 1958.

“I didn’t want to rock the boat,” Conaway says. “I was nervous enough.”

His going solo in front of the Beach Boys — “cruel and unusual punishment,” Conaway says, in hindsight — got props in the local press. “Robert J. weathered the tough spot of opening for a legendary group with eclectic, original acoustic tunes,” wrote Tom Alesia in The Capital Times. In the Wisconsin State Journal, Natasha Kassulke called his performance “soulful.”

Singer-songwriter Robert J. Conaway is leaving Madison after nearly four decades.

Singer-songwriter Robert J. Conaway is leaving Madison after nearly four decades.

I was there for some of Conaway’s earliest Madison gigs. At the Boar’s Head restaurant behind West Towne Mall — the name changed from the Stag and Hound in 1982 — he sat on a stool in the back corner of the bar and sang and played guitar.

Other nights, Rick Tvedt played. Conaway and Tvedt forged a close friendship that endures. Tvedt founded the Madison Area Music Awards in 2003. In 2015, when the Conaways had some unexpected medical bills, Tvedt helped organize a benefit at the High Noon Saloon that drew 350 people. The Conaways then proposed and helped seed the ongoing MAMA Cares program, which helps local musicians in times of crisis.

Conaway’s four decades in Madison is easily his longest stretch in one place. His family moved often when he was young.

“My dad worked for the Canadian National Railroad,” Conaway says.

I wondered if he was familiar with Gordon Lightfoot’s “Canadian Railroad Trilogy.”

Conaway immediately broke into the song. “There was a time in this fair land when the railroad did not run. When the wild majestic mountains stood alone against the sun.”

He paused.

“It’s one of my all-time favorites.”

Conaway had been living in Crested Butte, Colorado prior to coming to Madison. He’d briefly tried Los Angeles. “It ate me up and spit me out,” he says.

Madison did not. Here he played thousands of gigs and wrote hundreds of songs, winning a Billboard songwriting contest in 1999 for “A Million Miles Away.”

Conaway released numerous recordings during his time here as well, starting with 1986’s “Boys Town.” In departing, there’s a new release, “Barland,” a Rowdy Prairie Dogs CD out this month. It can be accessed through Conaway’s website.

Conaway intends to keep making music at his new home on the East Coast.

“My retirement fund is playing until the day I die,” he says. “I love it.”

He adds, “I’m excited to try something new. I’m going to rebuild an old workshop in my new house. Make that into a studio and keep creating.”

Conaway has heard there are numerous venues along the coast that may welcome a singer-songwriter. He says he has a new mantra:

“Will play for lobster.”