Honoured as Dan Mangan is to have Are We Cool Now? based on his songs, the much-loved Vancouver singer admits he hasn’t actually seen the indie-rock-flavoured play yet. As a result, he has things he’d like to know when he sits down with writer Amiel Gladstone and the Georgia Straight at Elysian Coffee near Broadway and Main.

“This is a general question, but I honestly don’t know the answer,” Mangan says inquisitively. “Do you need any precursor knowledge of my music to get into the play?”

Gladstone—who wasn’t overly familiar with Mangan’s records when he got the initial idea for Are We Cool Now?—is quick with his response. Based on a recent early mounting in Kamloops, he says, it’s okay if you don’t know Mangan from Mandingo. That might be, he suggests, because Are We Cool Now? was written to appeal to anyone who’s spent at least part of their time on this planet feeling hopelessly lost and adrift. The production—which has a live band re-creating Mangan’s songs, including a new original—focuses on a couple in their 20s setting out on a road trip, only to have the crushing realities of life lead to some serious reflection. In what’s being billed as a “rock music/theatre fusion”, the play’s main characters, stuck together while travelling, end up questioning everything from their place in the world to their relationship with each other.

Gladstone can relate to their struggle, and not just because he wrote the story.

“I was curious about that time of life, when you have more energy and things feel much more extreme,” the playwright says. “You can be more hopeful and also more devastated. In your late 20s, it’s a time of massive change, often hard and not pleasant. That was me for my late 20s—I was broke and depressed.”

That doesn’t mean that Are We Cool Now? is an unrelenting downer. Gladstone, a veteran playwright whose recent credits include directing the hit Cinderella: An East Van Panto, understands that no one wants to head home feeling like it’s time to reach for the rusty razorblades in the medicine cabinet.

“I always write trying to add as much humour as possible,” he offers. “I feel that’s important. And, well, I like laughing. But I know that some people have been surprised that it’s not just an all-out good time—there is some serious stuff that gets touched on. So I guess it does feel a bit bittersweet—it’s not just a full-on, all-out comedy.”

Gladstone also had a more ambitious motive for Are We Cool Now?.

“What I always wish about the art form that I’m doing is that more people my age, or around my age as I get older and older, is that more people in their 20s would come and experience theatre. It feels like the audience is always 45 and up. That’s always felt like something that I, as much as possible, want to change, even as I approach 45.”

And what better way to connect with a younger demographic than by building Are We Cool Now? out of Mangan’s songs? Since breaking out of the underground with the 2009 hit “Robots” (which—sorry folks—isn’t in the play), Lotusland’s favourite DIY troubadour has established himself as one of the most keen-eyed songwriters in the country. Mangan’s work touches on everything from spending time with aging relatives to Main Street hipsters to the inevitability of death. What’s held true over the course of four critically lauded full-lengths is that his songs often seem happy on the surface, but dark at their centres.

“I liked that his songs were lyrically interesting and emotionally complicated, but not immediately bare, like mainstream pop,” Gladstone says of discovering Mangan’s songs. “Something about the intricacy of his work made it really interesting to me.”

Mangan elaborates on that: “I recently had a conversation with someone about what makes a hit song. When you say to someone, ‘I kissed a girl and I liked it,’ what’s it about? The answer is about kissing a girl and liking it. What’s ‘Umbrella’ about? It’s like, ‘When it’s raining, you can come under my umbrella.’ Hit songs are so insanely easy to explain.

“Maybe that’s why,” he continues with a laugh, “I’m never going to have a truly big hit song. All my songs are ‘Well, it’s kind of like it’s good, but you’re worried about the fact that it might get less good, but then you know it’s good intrinsically underneath.’ ”

Kind of like Are We Cool Now?, the title of which was inspired by a line from Mangan’s 2009 ode to being unhip, “The Indie Queens Are Waiting”.

“This is a funny one to talk about, because I made this thing, with Dan’s permission, out of his music,” Gladstone says. “And he doesn’t even know what the show is.”

And, for Mangan, that’s been part of the fun.

“I sat in for an hour and a half or two the other day, at the rehearsal and with the musicians,” Mangan says. “That was a weird experience, to hear your music—many songs, not just one cover song—over and over again, done in a really different style. That really made me focus on the lyrics. Hearing someone else sing them, I was like, ‘Hey, that’s a pretty good line. Man, that song’s not bad.’ Because what happens is that you start forming opinions of your own work once you’ve played a song 800 times.

“But I don’t know what the narrative is here, and I don’t know what the story is. I’ve kind of purposefully been at arm’s length from all this, because I know it would be hard for me to get involved and then not get really, really involved. I’m trying to trust Ami’s vision and trust the musicians.”

Are We Cool Now? runs from Wednesday (September 30) to October 10 at the Cultch’s Historic Theatre.