Ron Sexsmith builds on breakthrough with bittersweet CD

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.