05/16/2014 04:16 EDT | Updated 05/16/2014 04:59 EDT

How Jann Arden Became One Of Canada's Most Beloved Singers (INTERVIEW)

I spent most of the nineties strutting around in an indie snob haze, indiscriminately snubbing anything that might be considered even mildly popular or, God forbid, mainstream, but I have always had a soft spot for Jann Arden.

No matter how massive "Insensitive," her biggest hit, got in 1994 and 1995 (and it got huge, hitting number one in Canada and Australia, cracking the Adult Contemporary Top 10 in the U.S., and making an integral appearance in the romantic Christian Slater film "Bed of Roses"), no matter how many times I heard "Good Mother," and "I Would Die For You" on radio stations I'd otherwise refuse to listen to, no matter how many friends' moms bought her albums, I refused to stop listening to her or even relegate her to a guilty pleasure.

I even snuck an Arden song or two on the mixtapes that I made for my like-minded friends and discovered that many of them adored the singer/songwriter with a penchant for heartbreak ballads as much as I did. Something about the haunting edge to her saddest songs and about the plaintive and honest lyrics of hits like "Could I Be Your Girl" turned us into completely earnest Jann Arden fangirls.

Two decades later, that same something compelled me to temporarily abandon any sense of professionalism and tell her all of this in the middle of an interview about her brand new album, "Everything Almost." One minute we were talking about how working with legendary rock producer and visionary Bob Rock pushed her out of her comfort zone and forced her to look at her music in a whole new light, the next I was gushing about the Arden-laced cross-country mixtape ring of my youth.

On the phone from a hotel room in Toronto, in the middle of a whirlwind media tour in support of the new disc, Arden sounds flattered – and patient – but she doesn't seem particularly surprised by my confession. I get that sense that she's heard all of this from similarly-minded fans before. And that the affinity is mutual.

"I fell like I've always kind of had this appreciation of the indie community," she says. "I think the only thing I really kind of hit with in a commercial mainstream way was 'Insensitive.' I mean, that was twenty years ago. My records were far different. I think they appealed to a far different demographic. I'm very grateful that I had that opportunity because it opened doors for me that were unimaginable, and to still have that kind of support from people that can sometimes shy away from things that are massively appealing.

"But honestly, I don't think I've ever appealed to the mainstream on that kind of scale. I think I've just been on the edge of that my whole career and I think there’s something really great about it because it's given me longevity."

Being different or not easily categorized bothered Arden in the early days of her career. "I never really got told that I was like anybody and I remember being really concerned about that," she admits. "Like 'Wow. I'm not like anybody. This could be really bad.' But I have people say 'You don't sound like anyone' and now I really appreciate that.”

The intimacy of her lyrics – one of her most powerful and popular attributes now – was also an issue for her in the early days. "I was told that my songs were too personal and that they would never work. I was turned down by everybody. I was turned down by my own label. I got the greatest rejection letters," she recalls. "It was like, 'I think you should be more generic and not so emotive when you're singing.' You wouldn't believe the shit they told me."

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For some labels, the content of her songs wasn't the only issue. "'You need to sing higher' was one of the comments I remember reading. Literally 'sing higher.' Let's really annoy everybody!”

The writing and recording process for "Everything Almost" came with its own challenging and, she admits, occasionally aggravating feedback. Rock knew what she was capable of and was not shy about pushing her out of her somber ballad zone. But Arden was far more receptive to his criticism because she knew that he wanted the best for her and her album. She trusted his vision even when she couldn't fully see it herself. And even though he might have asked her to sing a few notes above her usual range, he certainly didn't ask her to be more bland, more generic about her feelings, or sound more like anyone else.

That challenge began last summer when Arden assembled a collection of songs that she thought would make a decent album. She sent them to Rock. He didn't agree.

"Bob just said 'You know I got your songs and I've been listening to them and I just don't think we're ready to record. We've got four really great songs here. Maybe five. But you need to go back to the drawing board and try not to be you.' And I knew what he meant. It wasn't offensive. He was just like 'You've got to look at things from a different perspective.' It's almost like don’t plagiarize yourself. Think outside of being too precious about ballads. Find the tougher side of you. So that's what I tried to do. And it's not like I wasn't me. But he certainly got me out of wanting more than just OK," she says. "I think every artist needs someone to tell them they're full of shit. And I honestly wasn't used to anyone telling me that."

Once she had the right songs, Rock continued to challenge her and her band in the studio. "He was definitely a sensei pushing me. Bob, he's a very eccentric person. He just has this way about him. He's very much in his head when he's working and a lot of times when he was doing things and creating these soundscapes, I felt like I was on the outside looking in because I was like 'Oh my God! Where are we going?' Every couple of days he literally took me aside and said 'Jann, do you trust me? Jann? Jann?'" she laughs, impersonating a very zen-sounding Bob Rock.

"So I heard my name a lot, but I'm so glad he pushed me. I'm very lazy. A lot of the time, I can be very lazy and I needed someone to say 'Listen, you've kind of become complacent and you need to get yourself out of this place where you think being safe is fine.'"

The result of that effort and slight discomfort is an excellent new record that isn't a wild or disingenuous departure from her Arden's former work – as I probably would have said in the nineties, it's not a sell-out – but a solid and assured evolution. Melancholy ballads, in moderation, sit next to confident new pop sounds and new lyrical perspectives. There's even a slightly self-deprecating but unabashed love song thrown into the mix with first sing "Love Me Back," which Arden calls "kind of ABBA-esque."

With the music in place, there was only one more Jann Arden hallmark left to mix up: Instead of using yet another photograph of herself for the album's cover, her superstar manager, Bruce Allen, suggested a piece of art by Mandy Stobo of Bad Portrait fame. He'd read an article on the Calgary artist and thought a bad portrait of Arden was just what the album needed.

"He was just like 'Who the hell needs to see another picture of your head?'" she laughs. "I certainly think people in this country kind of know who I am, but we also wanted to say that we're moving forward. I think that's what the album says, too. It's everything, but not quite. I still have something to say."