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Little did Justin Roberts know when he was working at a Minneapolis preschool while playing in a goofy indie-folk-rock band called Pimentos for Gus in the early-mid-’90s that he was taking his first steps on the road to the Grammy Awards.

“I’d be in my apartment with my guitar,” the just-turned-41-year-old musician said from his Evanston house, “and I’d start writing a song about my cat.”

At first he wrote with his little students in mind, then kept coming up with such kid-friendly fare even after he left the preschool, realizing that playing late-night rock shows then caring for 3- and 4-year-olds early the next morning wasn’t the best combination. These songs were too silly even for Pimentos, so Roberts recorded some of them on a four-track cassette recorder and sent them to friends, including Liam Davis, a buddy from Kenyon College in Ohio who also had moved to Minneapolis to make music.

“I thought, ‘Oh, my God, these are fantastic,'” recalled Davis, who soon would spend a weekend with Roberts recording his lo-fi folkie kids songs at a Wicker Park studio for what would become Roberts’ first kids album, “Great Big Sun” (1997), even as the singer prepared to enter the University of Chicago as a religious studies grad student.

Cut to 2010, and Roberts finds himself in rarefied company. He learned this month that his seventh album, “Jungle Gym,” is vying against works by They Might Be Giants (“Here Comes Science”), Pete Seeger with the Rivertown Kids and Friends (“Tomorrow’s Children”), the Battersby Duo (“Sunny Days”) and Judy Pancoast (“Weird Things Are Everywhere”) in the Grammys category for best musical album for children.

Roberts, who had submitted his previous two albums to the Grammys after becoming a member of the National Academy of Recording Arts and Sciences, said of course he hoped to get recognized, but “this was a total shock at the same time.”

His ascension is especially impressive, given that the Grammys are the music business’s official self-recognition arm, and Roberts has released all of his albums independently, with stockpiles of CDs in his basement and garage awaiting distribution through an arm of Sony Music. As his friend and fellow Chicago musician Robbie Fulks wrote on his blog: Roberts is “somewhat in the position of the token Welsh art film up for best picture at the Oscars — which makes rooting for him all the more pleasurable.”

Yet Roberts’ national cheering section is considerable. Kathy O’Connell, longtime host of the radio show “Kids Corner” on Philadelphia’s WXPN-FM, not only chose “Jungle Gym” as her top 2010 album but prepared a “how dare they not recognize him” screed against the Grammys just in case Roberts wasn’t nominated.

“Justice prevailed,” she said.

Dan Zanes, who went from leading the 1980s Boston rock band the Del Fuegos to becoming a Grammy-winning family performer with his rootsy, genre-jumping albums, is a Roberts friend and fan as well.

“He’s just been making really great records for a really long time, and he’s got a clear path, and it doesn’t feel like he’s wildly tried to grab the brass ring,” said Zanes, who has swapped touring and other music-biz tips with Roberts over the years. “I believe in the way he’s done it, and it’s encouraged me. I never feel like he’s taking shortcuts, which isn’t always the case.”

“It’s definitely the year of Justin,” said Stephanie Mayers, an executive producer of the annual KindieFest family music conference in Brooklyn, where Roberts performed this spring. “Right time, right place, he’s built it up to the right level. This album, itself, people are really responding to.”

Having left the University of Chicago to devote himself full time to his music in 2001, Roberts lives in a bright, uncluttered home with a turntable and sizable record collection in the living room, the odd vintage movie poster on the wall (the 1968 Frank Sinatra detective yarn “Lady in Cement,” with the tag line, “This is the action picture!”) and a huge, shaggy, tawny Briard who looks as if he loped off the set of “The Empire Strikes Back.”

Roberts has an appropriately boyish look for a kids rock star: floppy brown bangs, narrow wire-rimmed glasses, homey sweaters and a bright, open face that might as well have “nice guy” tattooed across the forehead.

“And he’s always smiling,” Zanes said.

His voice is on the high end with a clear tone; he gets a lot of James Taylor comparisons, though R.E.M.’s Mike Mills could be a close cousin as well. He’s also been called “the Paul McCartney of children’s music” (O’Connell, quoted in USA Today) and “the Judy Blume of kiddie rock” (The New York Times’ Jodi Rudoren).

That McCartney-Blume intersection makes sense in that Roberts excels in hooky pop-rock songs that have an uncanny ability to get inside the heads of his single-digit-age listeners. Roberts and his wife, Chris Roberts, a north suburban middle-school teacher, don’t have children, but he has a powerful memory for what thrills, torments, amuses and tantalizes your average kid.

“A lot of times when I’m writing songs, I have to try to remember experiences of what happened to me when I was a kid, and I think a lot of those images stick in my head,” Roberts said. “Like I’m trying to write a song about Halloween, and I’m thinking: What do I remember about Halloween? I don’t really want to write a song about goblins and ghosts or anything. The only thing I remember is trying to collect as much candy as possible, and you would get home and sort through it all — that feeling.”

So, out came “Trick or Treat,” a “Jungle Gym” song that held the No. 1 spot on “Kids Corner” for much of October. The album is driven by such nostalgia. It has a whimsical cover rendering of an old-school jungle gym overgrown with vines bearing a pumpkin, a treasure chest and other fun objects. Inside are songs that celebrate a “Gym Class Parachute” and “Snow Day” and tunes that voice the feelings of a kid who gets separated from his mom in a mall (“Never Getting Lost”) or breaks his arm falling from, yes, a jungle gym (“Sign My Cast”). That last song, a tuneful ballad accompanied by a melancholy French horn, is wryly complex: As it begins, the boy is feeling sorry for himself, but in the end he is relishing his schoolmates’ lining up with their markers.

“Who puts passive aggression from a kid into a song for kids?” O’Connell said, laughing in reference to “Sign My Cast.” “And yet he captures it perfectly.”

Said Davis, who produced all seven of Roberts’ albums: “He’s somehow able to inhabit this character that is — I don’t know what the word is — bemused. The little kid in his songs, there’s something kind of cool about him. He’s still filled with wonder and is experiencing the world anew, but he also has this sardonic almost detachment.”

Roberts said he considers songwriting a difficult process as he fine-tunes his lyrics and hones his craft just as he would if he were writing for adults.

“I don’t think there’s that much difference between trying to imagine being a kid or trying to imagine any character you’d create as a grownup,” he said. “If Bruce Springsteen is telling a story of a blue-collar worker and telling the story of his life, he’s getting inside his head. I think the process is very similar: believing in your characters and imagining what they would think and feel.”

Some ask Roberts whether writing for kids is a limiting experience, and he has written the occasional adult song — he’ll be part of the Songwriters Circle, hosted by Ingrid Graudins on Jan. 23 at Space in Evanston — but he said he enjoys the challenge of saying what he wants to say in the kids-music context. Graudins said at the Space event that she plans to sing “2 x 4,” the sublime closing ballad of “Jungle Gym,” in which the narrator envisions rising above his troubles by way of a backyard ladder.

“Over the course of making all of these different records, it’s been really interesting to keep mining that and keep exploring that kind of songwriting, because I keep finding that the audience will go with me to places I don’t expect them to go,” Roberts said. “I’ll have, like, a 4-year-old come up to me and tell me that this little ballad is his favorite song on the record, and I’m like, ‘Wow, that’s the song I like, but I didn’t think a kid would really like that.'”

He added: “I wasn’t initially planning on being a kids musician, and when I decided to do it, it’s been an amazing experience. Playing for families is really fun. I find the audience to be a lot more interesting than just playing for a group of adults who are going to clap after every song.”

Justin Roberts and the Not Ready for Naptime Players perform 2 p.m. Dec. 29 at the Field Museum. Tickets are $5 ($4 for members); call 312-665-7400.

mcaro@tribune.com