Quick: what does the term cabaret music mean to you? Does it bring to mind the songs of Kurt Weill, Marlene Dietrich, or Weimar-era Berlin? Old Hochtaler ads or Liza Minelli in a bowler hat and stockings? Edith Piaf singing in Pigalle? Or maybe the Great American Songbook?

For Patricia O’Callaghan, one of Canada’s reigning queens of the amorphous genre and a pioneer of its contemporary form, it denotes much, much more. Take her new album, with Toronto’s Gryphon Trio, aptly called Broken Hearts and Madmen: it encompasses a mariachi number, a tango-fired Astor Piazzolla operetta song, an Elvis Costello ballad, and a hauntingly moody rendition of Nick Drake’s “River Man”. She’s also just released an album completely devoted to Leonard Cohen. Yet somehow in the hands of the blond-cropped chanteuse, all the pieces take on the smoky, nocturnal soul of cabaret.

“I don’t really see the barriers between genres; I don’t see there being any barriers. It’s all just music to me. Ultimately, songs are just songs, and for me, they could be from any genre, depending on the arrangement,” the artist tells the Straight over the phone from her Toronto home on a sweltering southern Ontario summer day. “It’s just poetry set to music; the harmonies are never going to be that different, whether it’s pop or classical or folk. A solid song with a good text and a good melody can really go anywhere you want to put it.”

People’s openness to cabaret in both its classical and contemporary forms has improved wildly since O’Callaghan began her career as a singer almost two decades ago. We’ve had a hit movie devoted to Piaf, watched the rise of a new meld of neo-burlesque and cabaret, and flocked to German-born cabaret diva Ute Lemper at MusicFest Vancouver, where O’Callaghan is set to appear this year with the Gryphon Trio.

But the music world wasn’t always so welcoming of the form. Raised in northern Ontario and then classically trained at the University of Toronto and the Banff Centre for the Arts, O’Callaghan just didn’t feel like she fit into the restricted world of opera and craved the emotional pull of cabaret. But when she started out, few knew where to slot her in a music industry confined to labels like “jazz”, “pop”, and “classical”.

“When I first did it, I couldn’t find anyone else who was doing it. It felt like the most radical idea!” marvels the artist. “I remember reading journal entries from way back then saying ‘Is it a crazy idea to want to do things like [Francis] Poulenc or Weill and sing them in a bar? Can I even figure out a way to do this with my life?’ And it’s so cute to read that now.

“But nowadays, this whole genre of cabaret is not uncommon. You actually hear it as a genre now, and when I started out it just didn’t exist.”

Although O’Callaghan has sung the greats, like Weill (she played Polly Peachum in the Vancouver Opera production of his and Bertolt Brecht’s Threepenny Opera in 2004), it’s the way she’s pushed the bounds of the repertoire that has set her apart from, say, the European stars reviving cabaret. Though her songs come from a variety of sources, O’Callaghan says they all have to affect her emotionally and the lyrics have to speak deeply to her. It’s key, she says, to helping her tap the soul-baring honesty that cabaret music demands. But don’t think it’s always easy; singing authentically, as it turns out, isn’t just a matter of hitting a switch and pouring out your heart on-stage.

“Quite honestly, I feel that I’ve strived for that all my life,” she says of releasing that emotional authenticity in her voice—an authenticity that manages to come through without dulling the polish that holds over from those years of classical training. “It’s taken me a really long, long time.…I’ve really strived to connect my voice with my heart, but I have to work at still not losing myself in it too much, because then you’re not giving to the audience; you become indulged in the song in a way. It’s a very fine line, I feel.

“You’re never going to be perfect and it’s going to be something I will always be trying to do for the rest of my life. Truly, there are days when I don’t even feel like I know how to sing—and I think that’s a good thing!”

Despite all the pain and hard work that go into preparing a piece of music, O’Callaghan admits the actual performance is a release that’s entirely different. “By the time I get to be on the stage, it’s pure joy for me. It’s just a pleasure to do; it’s not work for me. It’s exhausting, but it’s a very satisfying experience,” she explains thoughtfully. “At the beginning of my career, I was wracked with nerves all the time and it was quite painful, but I think, hopefully, at this point in my life being on the stage and performing is really, really pleasurable. You’re not thinking of technical things at that point—you’re past that.”

Still, there’s no doubt that technical demands are a factor when she’s first attacking a song—and that’s particularly true of her work with the Gryphon Trio. Like O’Callaghan, the virtuosic ensemble is known for pushing its art form—in this case, chamber music. But blending its eclectic, highly musical approach with her varied repertoire was something entirely new for both sides. She met the ensemble when it performed Christos Hatzis’s 2000 multimedia music-theatre work Constantinople, and they’ve been working together on and off ever since. Though they come from different fields, it’s been a surprisingly good fit, O’Callaghan says—and not just because she and Gryphon cellist Roman Borys share a love for Mexican music, which features on several of Broken Hearts and Madmen’s tracks. (For O’Callaghan, her love of the music started on a yearlong student exchange to the country during high school.)

“We have so much respect for what the other does in their respective fields; I mean, I’m just in awe of the beauty of their playing,” she says of the Gryphon Trio. “I can do different styles of singing, but I’m classically trained, so I can go in and read a fairly complicated arrangement with them—like a classical musician would—but I don’t execute like a classical musician. You kind of have to have that working method to work with them.

“For me it’s challenging, though, because in my normal cabaret thing I just lose myself in the song, and with them, you can’t lose yourself in the same way—you always have to know what everybody’s doing at any given moment….You want that emotional attachment,” she adds with a soft laugh, “but you want that musical sense of where you are.”

This year, she’s touring their album, and Matador: The Songs of Leonard Cohen, far outside the traditional, smoky club digs of cabaret. O’Callaghan has become accustomed to opulent concert halls—but also to the world of summer festivals. Here, she and the trio will perform in the intimate, acoustically sparkling new Orpheum Annex.

Just as she embraces all forms of music, O’Callaghan happily welcomes all kinds of venues.

“I love doing summer festivals, because they have such a nice vibe, and more often than not we end up playing in a church in the middle of nowhere and there’s a bunch of cows outside,” she says. “Plus the acoustics in the church are amazing, and you don’t use any miking.” And that may be the most solid proof of how much cabaret has evolved, and how far O’Callaghan has ultimately taken it, from its origins: a summer fest on a sunny day is pretty much the antithesis of the dark, gritty underworlds where cabaret formed.

Patricia O’Callaghan and the Gryphon Trio perform at the Orpheum Annex next Thursday (August 16), as part of MusicFest Vancouver.