Playing With Men is another deeply personal and thought-provoking show from Jon Bennett, reflecting on his early years as a talented junior footballer in Southern Australia. His football career, once filled with promise, faced an abrupt halt when real-life challenges and a community tragedy forced him to reconsider his path. Now, as a celebrated comedic storyteller, Bennett uses this show to explore themes of masculinity, community, friendships, life, and death, all through the lens of football.

Despite Bennett’s shift from the football field to the world stage as a multi-award-winning performer, Playing With Men touches on how certain experiences, especially those shaped by traditional masculinity, remain ever-present. It’s a mix of humor and heartbreak, with Bennett tackling heavy themes while never straying too far from his comedic roots.

The show has received critical acclaim, including a Just for Laughs Best Comedy Award nomination (Montreal Fringe, 2016), a Best Storytelling Award (Sydney Fringe, 2023), and an Outstanding Storytelling Award (Victoria Fringe, 2019). It has been described as both "side-splittingly funny" and "crushingly tragic," with Bennett's honesty, wit, and self-reflective charm captivating audiences.

Just for Laughs Best Comedy Award nomination (Montreal Fringe, 2016)

Best Storytelling Award Winner (Sydney Fringe, 2023)

Outstanding Storytelling Award Winner (Victoria Fringe, 2019)

“ A tour de force who will make you laugh–to tears. ★★★★★” - Otakuno Culture

“Bennett expertly engages us with his wit and self-deprecating charm, so this is a performance we enjoy and endure, together. It is successful in combining the release of a good laugh with a depth of meaning we must process afterwards. ★★★★½” - Stage Whispers

”What I love most about Bennett is he’s an artist who doesn’t just make you laugh or cry, he makes you think. And in Jon Bennett: Playing With Men, he’s at his best.” - London Free Press

“Side-splittingly funny and scathingly self-critical, it’s a valuable work that probes at toxic masculinity and the culture of machismo.” - CVTV

“Made me laugh until I cried. Then laugh some more.” - Theatre In London

“Both funny and crushingly tragic. ★★★★” - Check the Program

“This friendly show is hard not to love. ★★★★” - The Australia Times

"Charming and funny" - Orlando Sentinel

"The gifted story teller engaged the crowd so skilfully, within moments of the show starting you had the impression that you had known Jon since childhood. I couldn’t shake the disarming feeling of intimacy for the entire duration of the show." - CJLO Montreal

"No one can observe life quite like Bennett. His delivery is infectious. Hysterical and heartfelt. A perfect example why Bennett is so excellent as a performer. His authenticity is disarming and invites self-reflection. He doesn’t hide behind his humour or have a schtick. Bennett is so honest about himself, so uncensored and willing to share himself as he is. He talks about events and things that other people would rather forget — and not just the ones that are embarrassingly funny, but also the ones that show a raw, sensitive heart. Just hearing Bennett has the sensation of making one a better person, because he invites the same kind of recognition as he accepts in himself. We are all perfectly imperfect beings." - Montreal Rampage