Ash Flanders Is 'Playing To Win' In His Never Ending Quest For Success

Success — everybody wants it, if only we knew what the hell it was. Is it having notoriety and fame, dogged by fans on every street corner? Is it having the respect and adulation of your peers, complete with a mantle groaning with trophies? Or is it having a million Instagram followers and your own hashtag? As Ash Flanders' musical cabaret Playing To Win explores, the quest for success is not as straight forward as you might expect. And after all, as Flanders notes, "the hunt's more exciting than the kill."

By any yardstick, it would be hard to argue that queer renaissance man Ash Flanders isn't a success. In addition to being one of Australia's most lauded cabaret acts, the all-singing, all-dancing, all-gendered performer and theatremaker is also one-half of pioneering indie theatre collective Sisters Grimm. Most recently, he has co-starred alongside Peter Paltos in comedy web-series Friendly.

All in all, Flanders' CV makes for impressive reading, but he's not letting that get in the way of putting his achievements through the wringer. "I think my headstone will read: 'Here lies a cautionary tale'," he proclaims with on-brand flamboyance. "I do get very personal in my solo work, because I'm really fascinated by the things that make us afraid, and revealing so much of myself on stage is pretty scary for me. When you're a performer and you're used to being in front of an audience portraying a character, revealing your true self on stage is one of the few scary things left. But, I truly believe that wherever the fear is, that's where you should go as an artist, because that's where the good stuff is."

 "When you're a performer and you're used to being in front of an audience portraying a character, revealing your true self on stage is one of the few scary things left."

Playing To Win, co-created with Stephen Nicolazzo, is Flanders' third solo cabaret show, in what could be viewed as a trilogy chronicling what it means to be an artist, or perhaps more accurately, why it's ultimately impossible to "win" at being a performer. After a highly praised debut at last year's Melbourne Cabaret Festival, picking up a Green Room Award for Best Writing in Cabaret along the way, Flanders should be confident heading into Playing To Win's first revival, as part of Midsumma's cultural program. Except at the core of this show is a knowing wink to the crippling anxieties any artist worth their salt is racked by.

"The entertainment biz has, broadly speaking, always been about the same thing: getting attractive people to stand in front an audience so we can all gawk at them. Even in the gay world, I'm not a ten, so I've always seen myself as the 'funny guy' on the sidelines looking at it all and trying to work out how on earth I fit in there," Flanders shares. "It's funny in a place like Australia, where I think it's still very much about pretty people on TV or pretty people on stage. It's still really hard to find your niche, or figure out what you offer. Then to make that into something that is viable and can be your life's work is a very, very difficult thing. I love making my own work, and it's what I'm really passionate about, but then again, I'm 35. It's a little too late to go back now — I really should have learned Mandarin and accounting."

This may sound all very profound for a bit of camp comedy, but anyone familiar with the work of Sisters Grimm won't be surprised that Flanders has plumbed such existential depths for his cabaret work, although by his own admission, his solo shows help him satisfy a guilty pleasure. "It's where I indulge in my love of real life, low-brow pop-culture. I'm not afraid to admit it," he confides. "With Sisters Grimm, queer is the form — we're interrogating a narrative to reveal the otherness of it. But in my solo work, if I want to do a monologue from Judge Judy, that's what I'll do. In fact, that's what I did do in my first show — weirdly, that was everyone's favourite part! I just kind of follow my nose, and my natural obsession for weird pop-culture, but I think it's oddly universal. Maybe people just like it in the same way a dog standing on its hind legs is interesting for a lot of people — it's instantly accessible."

Like many comedians, Flanders' shtick is fuelled, at least in part, by darker qualities of his personality, although he believes this yin and yang mindset is typical of his post-babyboomer, pre-millennial generation. "I end sentences with a joke, I don't take anything too seriously — that's my natural voice. If you go beneath that, there's the cynicism and then there's the fear, and there's the deep subconscious churning away. I think that's beneath the surface of all of us, but my kind of ironic, detached, pop-culture soaked voice is a very familiar one to a lot of people my age, because they're the kind of people who grew up saturated in television, and then got older and a bit disenfranchised with politics and with the way you can't afford a house anymore. All you really have, in the end, is this armoury of personality traits. And maybe a Twitter account."

Ash Flanders presents Playing To Win, at the Arts Centre Melbourne, 27 — 29 Jan.