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Brady Rymer performs at Greenport Harbor Brewing Co. last Friday. (Credit: Glen Hoffman)

Brady Rymer, a Southold resident with three Grammy nominations under his belt for children’s music, was not always a kid-friendly entertainer.

More than three decades ago, Rymer and his then-burgeoning band, The Dogs, spent a week rehearsing a new song — The Replacements’ “I.O.U.,” a swaggering barn burner with lyrics railing against the major-label machine penned by one of its recent rabble rousing signees — to close out a bar gig in their Sparta, New Jersey stomping grounds. Their performance was cut short and the bar closed for the night before they could blast through the ‘Mats track. The Dogs departed for a party, after which they returned to the shuttered bar. Upon considering their hard work rehearsing all week, the group decided to commit a B&E to play I.O.U. at around 4 a.m.

“We looked around and we actually found a boarded up window so we didn’t have to break anything,” Rymer, 59, says. “We slipped in through the window, went downstairs, turned on our amps, played that one song and then we left. We ended up getting arrested that night.”

Long before Rymer, now 59, formed his Little Band That Could in 2000, which has since released 12 albums — three of which scored Grammy nominations for Best Children’s Music Album — and toured America and England, he was a music-loving young’un. He first picked up the guitar as a preteen at the request of his older brother who needed an axman for his band. Throughout junior high and high school, their garage band, Old Crow, named after the whiskey, played gigs loaded with covers of hits from musicians like David Bowie, The Rolling Stones, Led Zeppelin and The Grateful Dead, plus a smattering of originals. Rymer kept in touch with both the group’s drummer and its vocalist — Patrick Fitzsimmons and Todd Sheaffer — during their college years.

“We were sending cassette tapes back and forth of songs we were writing,” Rymer recalls. “Then we got together in New York City and made a go at making music full time. That band that started in junior high school survived.”

These Old Crow members picked up a few new musicians and formed The Dogs, which became From Good Homes following their arrest for rocking in the wee morning hours.

“We were in front of the judge a couple weeks later,” Rymer explains. “He said, ‘Well, since you guys are from good homes, I’ll let you off with a benefit concert for the youth of Sparta’ … That concert never happened.”

With the arrest in their rearview, the newly minted From Good Homes gigged feverishly before self-releasing their debut album, “Hick-Pop Comin’ At Ya,” a nod to a term one critic wrote to describe the band’s feel-good sound, in 1994. Shortly thereafter, the group landed a record deal with RCA thanks to attention grabbing performances at Wetlands Preserve, a New York City nightclub that welcomed post-Grateful Dead era jam bands the likes of Phish and Sublime before it shuttered in 2001. By the end of the decade, From Good Homes released four more albums, and toured with the likes of Bob Weir of the Grateful Dead and even once opened for Bob Dylan.

“We were part of that jam band scene that was happening at Wetlands and Irving Plaza,” Rymer says. “Dave Matthews would come up to New York to open for us and we drove down to Charlottesville to open for him. We played with Rusted Root and Blues Traveler. Hootie [and the Blowfish] came up and opened for us at Wetlands.”

From Good Homes also landed two songs — “Fruitful Acre” and “Wide Open Wide” — on the soundtrack for the 1997 film “Picture Perfect,” starring Jennifer Aniston, Jay Mohr and Kevin Bacon. The band members even make a cameo appearance in the film as a band performing at a Gulden’s Mustard advertising party.

So how exactly did Rymer the rocker become a family friendly household and schoolhouse name? For starters, he started a family of his own just before the group played a farewell show and amicably disbanded in 1999. Three years prior, he said he and his wife, Bridget, then pregnant with their son, Gus, penned “Last Night In Utero,” hoping the track would induce labor “because he wasn’t on time.”

“You have a guitar, and a new experience in your life; I just started writing songs for my kids about the experience of being a dad,” Rymer says. “Music was a way of experiencing all this … I wanted to document the songs at least as a gift to my family, to my kids.”

Starting with a small collection of new, family-forward material, Rymer performed at parties and school events around New York City where his family was based at the time. He decided to say “‘yes’ to everything” as he traveled this new path, be it more gigs, after school songwriting classes and collaborations.

“It was nice because I was able to keep creating and playing music,” Rymer says. “You dip a toe in the water and see how it feels, and [I realized] I missed playing with a band.”

He soon met a pair of musicians — mandolin player Liz Queler and keyboardist Seth Farber — whose children went to the same preschool as his daughter, Daisy. Along with accordion player and singer Claudia Mussen, they formed Brady Rymer and The Little Band That Could

“I really love being in a band; I’ve been in bands since the fifth grade,” Rymer says. “[Forming the band] was exciting because it wasn’t kiddie music at all. It was just real music, both something that families and kids would relate to. It was really fun playing with these musicians and playing these concerts.”

In 2009, the band recorded “Here Comes Brady Rymer and the Little Band That Could,” his first to earn a Grammy nomination. Nominations followed in 2014 for “Just Say Hi!” and 2017’s “Press Play.” The group received another honor in 2014 in the form of an invitation to perform at the White House for its annual Easter Egg Roll.

As the group ascended, so did Rymer’s now-adult children, from watching From Good Homes’ farewell performance from their strollers, to singing and laughing on their dad’s first few albums and even joining him onstage.

“You think rock’n’rollers would tear up a backstage?” Rymer asks with a laugh. “Get some elementary school kids and their friends, they can rip up a backstage.”

Today, Rymer balances performing and recording with his Little Band That Could with From Good Homes, which reunited in 2009 and released “Time and the River” in 2019. From Good Homes remained a beloved live act in their home state.

From Good Homes is looking to book some winter dates. “We usually do two dates around the Christmas holiday, so we’re trying to figure that out,” he says. We usually do a summer date or two, but this year it didn’t work out with everybody’s scheduling. People are in Vermont, people are in South Carolina, and then somebody’s touring. It’s kind of hard to get everybody together.”

On Friday, Rymer performed a solo set loaded with his adult material at Greenport Harbor Brewing Co.’s Carpenter Street location. Whether Rymer will fill more squares on his calendar with similar performances remains to be seen.

“I love going out at the wineries and seeing Gene Casey and Jon Divello,” he said. “So you never know.”