Running over three weeks from January to February, Midsumma is Melbourne’s largest annual pride festival celebrating queer, intersex, transsexual, transgender, bisexual, lesbian and gay culture.

Currently celebrating its thirtieth anniversary, this year’s jam – packed alternative visual and performing arts program features more than 120 different acts and events. Various entertainment options include musicals, comedy, drama, cabaret, film screenings, readings, art exhibitions, bands, forums, rallies, carnivals and raves.

An award – winning performer / writer, Ash Flanders fronts one of the must – see highlights of the 2017 Calendar.

Staged at Prahran’s Chapel off Chapel last June, Playing To Win was a featured part of Melbourne’s Cabaret Festival.  Following that success, the show returned to the Arts Centre in Southbank for a strictly – limited three performance season.

Playing to Win is Flanders’ fourth cabaret work, adding to an impressive and growing resume. Previous musical gigs include Meme Girls, Negative Energy Inc., and Special Victim. He has also been in plays such as in Buyer & Cellar (for MTC), Psycho Beach Party (Little Ones Theatre), and Hedda Gabler (Belvoir Street Theatre).

In a non – stop star turn, Flanders’s fronts an experience which faithfully follows, yet simultaneously, comically dismantles the stock cabaret template. He presents a glowing persona the likes of Sean Hayes’ Jack McFarland from television’s Will & Grace, My Life On The D – List’s Kathy Griffin, and Chris Lilley’s Ja’mie from Summer Heights High, brought to commanding and exacting life. Decked out in a sequined hoodie which eventually reveals a catty print leotard, Flanders engages enthusiastic audiences from start to finish.

Flanders links quirky gossip and personal stories, using a handful of power ballads from singers like Celine Dion and John Farnham. He knocks these thumping covers as well as several choice others, completely out of the park. (It should be noted that Playing To Win’s four piece band consists of drums, keyboards, electric and acoustic guitars. The quartet, musically directed by Dave Barclay, must be congratulated for their exceptional in – sync backing.)

There is something quite refreshing about the production’s non – linear structure, in that viewers are never quite sure what is going to happen next. Manic one second and quietly reflective the next, Flanders special performance takes us all over the store in his need to inform, shock and please.

Stephen Nicolazzo (from Little Ones Theatre) directs this journey with enlightening hilarity.

The quest for social recognition can be elusive at the best of times, and this show takes no prisoners in defining celebrity status.  From mocking the Real Housewives of Melbourne questionable talent, to confessing that he threw a public tantrum in front of his own parents, no one is safe (including Flanders) from his quick and acerbic wit.

Flanders even took to the room, mike in hand, asking the audience to join him in a group sing – a – long, where no one knew the lyrics. He did this, if only to prove the fleeting power of fame. It was one of the show’s defining moments, taking us behind the velvet rope into a crazy, parallel universe.

Sensing that Playing To Win added new material since its recent run at Chapel off Chapel, here’s hoping the format is continued for future reference.