TORONTO - As Ron Sexsmith was in the midst of putting together what would become his new album "Forever Endeavour," the Toronto singer/songwriter — who has become infamous for his utter lack of self-regard — couldn't shake an unpleasant feeling.
The material was simply sounding too good.
"I remember recording it and feeling almost a bit suspicious — 'Why is everything working out? How come everything is sounding great?'" Sexsmith said in a recent interview while relaxing in a plush booth at a Toronto diner.
"Because that hasn't always been my experience. There's usually a snag or some song that doesn't work."
But after the breakthrough success of his Juno-nominated "Long Player Late Bloomer" and an invigorating experience recording the follow-up, perhaps Sexsmith might just have to get used to things actually working out.
And yet, what's surprising about "Forever Endeavour" (in stores Tuesday) is that a recording experience described by Sexsmith as uncommonly smooth produced a deeply bittersweet, introspective set of songs.
"If Only Avenue" — an acoustic stroll coloured with elegant strings — finds the singer lamenting past mistakes, while the sprightly, horn-driven rave-up "Snake Road" similarly has Sexsmith looking back at a "destructive" period in his 30s, when he over-indulged in booze and the typical "cliche road" stuff at the expense of his home life.
It's actually a light-hearted song — as is "Me, Myself and Wine," a jaunty tune about the simple joy of relaxing with brassy instrumentation that calls to mind the crooked streets of New Orleans — that Sexsmith hoped might offset the record's darker moments.
Those sadder tunes, principally the jangling "Back of My Hand" and sombre "The Morning Light," were inspired by a health scare. Sexsmith had discovered a lump in his throat in the summer of 2011, and endured a tense few months of tests (some of which were conducted while the album was being made) before he received the medical all-clear.
"You start thinking: 'Aw, crap, what's this? Is this something I'm going to be fighting next year? Is it something they got too late?'" he recalled.
"So I had this three-month period where I was walking around wondering and worrying. (It) just got me thinking about all that stuff — where do we go when we die?"
At other points on the album, he probes a more familiar point of frustration: his career.
Gentle album opener "Nowhere to Go" finds Sexsmith at a particularly low point, cooing: "There's no way to stop it from pouring buckets from the sky/ When you're stuck in a cloud and there's nowhere to go but down."
The song was actually written prior to the release of "Long Player Late Bloomer," when a number of U.S. labels had a keen interest in Sexsmith's new material that very abruptly cooled.
"What happened was, when we started playing it for people, no one wanted it," he said. "I don't think I've ever made an album that had so much rejection initially, in the States.
"It sort of put me in a bit of a funk again."
Of course, that record would eventually become one of the biggest successes of the 49-year-old's career.
He attributes much of that to the sheen applied by studio wizard Bob Rock, the Winnipeg-born producer of Metallica and Michael Buble who's renowned for his skilful application of pop polish.
Yet Sexsmith made the somewhat surprising choice this time around to return to working with Mitchell Froom, the multiple Grammy nominee who has collaborated with Randy Newman, Sheryl Crow, Los Lobos and Sexsmith himself, on his first three major-label efforts.
The difference is striking, with Froom returning Sexsmith to the more organic sound on which he made his name. While the record is unadorned with overt production frills, it's hardly minimalist — the instrumentation is lively, varied and inventive.
He sees parallels with the last record Froom produced for him, 1999's "Whereabouts." That record was also packed with strings, horns and woodwinds but Sexsmith felt it turned out to be a "bit of a disaster."
"I felt that record was kind of doomed," he said. "This record, I felt we were doing that kind of album again but doing it right this time."
As for the reasoning behind his choice of producer, Sexsmith just felt this particular collection of songs would flourish under a different arrangement than the radio-ready pop of "Late Bloomer."
"There was something about these songs that sounded like classic singer/songwriter stuff — I was thinking of those albums from the '70s, like the kind of stuff that Neil Diamond would do that I always liked, or Gordon Lightfoot," he said.
"I felt this was the first sort of proper singer/songwriter album that I've made, really."
Still, he's hoping the transition isn't a shock for fans.
Particularly since "Late Bloomer" actually earned the singer some new ones.
"I know there's a lot of people that liked the last album. I picked up a lot of new fans," he said. "I was a bit worried that because that was such a different record that they might not like it without its polish."
Meanwhile, the inroads he made with that record gave Sexsmith a much-needed burst of confidence.
Prior, he had worried about "disappearing" into the Canadian music industry.
"I think the last album did a lot towards that, to making me feel like there's people out there that are into (my music)," he said. "'Cause I had been feeling before that my career was going down the drain."
Well, the success hasn't exactly gone to his head. Sexsmith is still witheringly self-deprecating.
When weekly magazine Now Magazine recently included Sexsmith's self-titled '95 record among a list of the 50 best albums ever to come out of Toronto, Sexsmith saw fit to write to the magazine and disagree with his placement, arguing that he'd yet to record a great album.
Similarly, he confides that while his short-listing for the Polaris Music Prize last year was a pleasant shock — "I always felt there was something really square about what I was doing that was never going to connect with a hipper crowd," he laments — it also invited an overwhelming amount of Internet scorn, to the point where Sexsmith was rooting against himself.
"I went to the Polaris awards hoping that I wouldn't win," he said. "Because I didn't want to upset anybody."
Even after giving an engaging, eloquent interview, he apologizes. He says he's sorry for his (fictional) inability to "string sentences together" on this frigid morning.
The same skilled songwriter lauded by Paul McCartney and Elvis Costello still seems capable of only intermittently summoning any measure of self-belief.
"I guess I'll always be a little bit insecure about where I sit in the whole thing," he said. "I guess it doesn't matter, ultimately. But I just keep trying to, with every album, try to make something that will connect."
Thus his goals are, in many ways, modest. He wants to summon sufficient buzz that he knows there's interest in his music, to the point where he knows he can afford to hit the road with his band.
And if you read between the downcast statements about his career, or his perceived shortcomings as a singer or arranger, Sexsmith seems to be slowly growing more comfortable in his skin as the albums and accolades pile in his rearview.
And, crucially, more confident.
"I've had albums that did well and some that did absolutely nothing. Throughout my career, I think I've been a better writer than a recording artist," he says. "I've always been proud of my songs I had on my albums but I haven't always been good about getting it across.
"I think I'm getting better at that side of it now, where it's coming together, the song and the production. And I'm singing better now.
"So I think I have a better chance now of having more of a breakthrough record than I did even when I started."