A self-described late bloomer, Jenny Whiteley didn’t decide to dedicate her life to music until she was 24. That she eventually chose art over a steady paycheck wasn’t, however, overly shocking. The Toronto-raised singer-songwriter, whose third and latest solo album is titled Dear, was born into a musical family: Her father is celebrated Canadian roots musician Chris Whiteley, her uncle Ken is a veteran session man who’s performed with everyone from Pete Seeger to Raffi. Her brother Dan, a guitarist and mandolinist, is one of Canada’s most respected bluegrass players.
But while music runs deep in her bloodlines, Whiteley never imagined she’d be making a living standing in front of a microphone. “With Dan, music was pretty much a done deal by the time he was 15,” Whiteley says from her farmhouse in rural Ontario. “He was totally obsessive about guitar playing by age 12. Everybody thought I would do music, but instead I went to university for anthropology.”
Even as she was cracking the books in Montreal in the ’90s, Whiteley was spending weekends in Toronto performing with the Junior Jug Band, a long-running family project specializing in old-timey music for the fresh-out-of-Huggies crowd.
“The ’80s were a boom time for kids’ music, so Chris and Ken decided to do an album,” she explains. “My brother and I sang on the record, and as time went by, we started performing with them more and more and then became a four-piece band. I played washtub and Dan played washboard. We actually sold 50,000 copies of our album — I’ve got a gold-cassette award.”
Dropping out of college after her second year, Whiteley made her first foray onto the bar scene with Heartbreak Hill, a throwback bluegrass band that became a live institution in Toronto. The group’s lone album, a self-titled 1998 disc, took home a Juno, the Canadian equivalent of a Grammy.
“One of the first songs I wrote was called ‘I Scare You’, a female-stalker kind of song which ended up on the Heartbreak Hill album,” she recalls. “It was kind of like beginner’s luck — I wrote some good stuff right off the hop, which meant I never got discouraged later on.”
If Heartbreak Hill made her one of Toronto’s favorite daughters, it’s as a solo artist that Whiteley has been embraced in the rest of the country. Hopetown, the 2004 follow-up to her eponymous 2000 debut, featured ten tracks of soft-focus, folk-tinted bluegrass, capped by the mandolin-burnished stunner “Halls Of Folsom”, a song as mixtape-worthy as the Johnny Cash classic that inspired it.
Dear finds Whiteley branching out. While “Banjo Girl” does bluegrass as authentically as the Lonesome Pine Fiddlers, she’s also determined to push herself in new directions. With her husband (and Sarah Harmer guitarist) Joey Wright riding shotgun, Whiteley swings effortlessly from black-hearted back-porch Americana (“Unsung”) to Laurel Canyon country (“Take Your Time And Do It Right”) to whiskey-hazed MOR (“Other Side Of Life”). The straight-outta-the-’20s gem “Write Me Away” revisits a time when squirrel nut zippers were the hottest candy in America, while the DIY-folk-rocker “Yellow Couch” highlights the beautifully organic production work of Vancouver studio man Steve Dawson.
Further marking Dear as a departure from her past work, Whiteley doesn’t shy away from using her own personal experiences for lyrical inspiration this time out. Nowhere is that more captivating than on the roots-pop heartbreaker “Indoor Lightning”; if you’ve ever let a relationship drag on long after it’s over, you’ll understand where she’s coming from when she sings, “There’s a cloud out there/But it’s stormy in here/And if you have to choose/I guess real thunder/Is safer than indoor lightning.”
“In my own mind, I figured that I’ve been doing this long enough that I’ve earned the right to write about myself,” she says with a laugh. “I don’t think there’s that much of you you can draw on when you’re 22 or 23, unless you’re really mature. Some people are, but I knew that I wasn’t interesting. With ‘Indoor Lightning’, that feeling where one person is leaving but the other is already emotionally gone is something that I’ve definitely been through.”
Whiteley’s finest moment on Dear, however, might be “When It Rains I Pour”, a pedal-steel-swept lullaby with a title that sounds like classic George Jones. There was a time when Whiteley might have shopped the tune to country radio; she’s worked with a Music City publishing company in the past. But because she got into the business for love rather than money, she isn’t overly obsessed with adding to her collection of gold records…er, cassettes.
“I’ve realized I’m not really a Nashville-country-radio-type person — I’m more of a singer-songwriter,” Whiteley says. “But I do have an idea for a really bad, cheesy, country song that I might have to write under a pseudonym and make millions of dollars. I can’t tell you what it is because someone will scoop it on me, but trust me, it’s so bad it’s good.”