Why did it take Justin Rutledge 18 years to record and release Jellybean, his most popular song?

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“If you listen to my work, you might think I’m a bit of a dreary guy,” says singer-songwriter Justin Rutledge. “But I assure I’m not. I can have fun.”

It’s quite an assertion. This is an erudite Juno winner and associate of Michael Ondaatje who is responsible for songs such as Weight of the World, Too Sober to Sleep and I’m Gonna Die (One Sunny Day).

Moreover, Rutledge’s 2008 album Man Descending was inspired by a 1982 book of the same name by Guy Vanderhaeghe, whose Governor-General’s Award-winning collection of short stories won over the turtleneck-and-elbow-patch people with its deft meditation on the desperations and humiliations of men.

And even if something like Rutledge’s Alberta Breeze sounds pleasant enough, it references a country that is “cold in autumn’s chains” and includes a line about a “tongue-tied beheaded bride.”

Are we having fun yet?

That said, fans of Rutledge who attend his concerts will testify to his well-hidden cheery side. For years, most of his shows have closed with the beer-soaked singalong Jellybean. It’s communal, with one of Canada’s most literate balladeers standing on a table rhyming “my Boston cream” with “don’t be so mean.”

It’s a wild juxtaposition – imagine Leonard Cohen vibing on a skateboard crooning a TikTok version of Louie Louie.

“It may not be easy to go to one of my concerts,” admits Rutledge, the Toronto troubadour known for tensely poignant songcraft and romantic earnestness. “But there is a payoff at the end. I feel like Jellybean is a great reward for sitting through one of my shows.”

Here’s the thing about Jellybean, though: Rutledge wrote it in 2003. And although it’s a signature song for him, it has never been officially released.

Until now. The fan favourite is the lead single to his ninth LP, Islands, out March 26. The other tracks are newly recorded acoustic versions of previously released songs.

But why now? Why has Rutledge kept the song in his back pocket for so long? In short, what reason has Rutledge had to be so mean to Jellybean?

“The song is just an acoustic guitar and a room full of people,” Rutledge explains. “You need it to be 1 in the morning, at the end of a busy night. It’s hard to record a song like that in the studio.”

It’s hasn’t been for lack of trying that Jellybean’s juju has yet be captured on tape. “This is probably the fourth attempt at recording it,” Rutledge says. “But it never made the cut.”

His new album Islands, however, was conceived as a studio version of a typical Rutledge concert. It begins with Come Summertime, a song that often sits atop Rutledge’s set lists, and closes with Jellybean, a song about unrequited love that cloaks its wistfulness in melody.

Whether or not Jellybean ever made it onto a Rutledge album or not, it’s an odd thing for a songwriter’s most well-known song to be such a stylistic outlier.

“I suppose if you hadn’t heard of my music before and you just heard Jellybean for the first time, you’d think I might be more closely associated with Fred Penner than with Michael Ondaatje,” says Rutledge.

One who doesn’t think that is Ondaatje himself.

“There is always a melancholy air in Justin’s songs,” says the lauded author, who collaborated with Rutledge on the stage adaptation of his novel Divisadero. “But just as it is in his song I’m Gonna Die (One Sunny Day), the melancholy is still there in Jellybean, even if it is disguised in the song’s humour.”

Fellow author Vanderhaeghe agrees. “Jellybean looks like it has a lot of unRutledgean sugar in it, a double dose since the girl in question is both his jellybean and his Boston cream. But, then again, he’s doing his desperate best to sweet-talk her out of her mean streak. Like marmalade, there’s enough bitter rind in the song to give it a little bite.”

Although Rutledge isn’t arguing – “There are certain lyrical elements in Jellybean that I like to think are representative of the rest of my work” – we shouldn’t expect Zip-a-Dee-Doo-Dah from him any time soon.

“Jellybean is the one bone I’m going to throw to people,” he says. “This is me writing a happy song. But elsewhere, I’m going to do what I do.”

Justin Rutledge performs an Islands livestream show on March 28, at sidedooraccess.com

Candy to Michael Ondaatje’s ears

The esteemed poet, novelist and dedicated Justin Rutledge fan Michael Ondaatje assesses Rutledge’s Jellybean, a three-chord campfire song in F# minor.

“Jellybean is a song where Justin simply hands it over to the crowd. They take over. A bit like Springsteen’s version of Tom Waits’s Jersey Girl, with the Jersey crowd going wild. I have heard Justin sing Jellybean many times, in many places, and it is always wonderful. He often stands on a chair to direct the audience. But I suppose my favourite one of his is 1855, about Walt Whitman. Justin is a great lyricist and poet too.”