If there’s one thing Kevin Flynn knows how to do, it’s keep an audience on their toes. Performing in New Zealand for the first time, Flynn wasted no time making it clear this wouldn’t be just another predictable night of stand-up comedy.
A blend of razor-sharp wit, chaotic energy, and personal reflection, his set was a rollercoaster of hilarity. Equal parts poignant and unhinged.
From the moment he stepped on stage, Flynn commanded attention. He’s the kind of comic who grabs the mic with the confidence of someone who knows he can make you laugh until it hurts.
His constant motion, paired with an ability to transition seamlessly between topics, made his performance feel more like an electrifying conversation than a rehearsed routine.
Beyond the laughs, Flynn wove in moments of reflection and personal triumph.
He shared that he has met four U.S. presidents and had personal conversations with them, the latest being an invitation to dinner at Donald Trump’s Mar-a-Lago estate. A setup that led to a hilarious recounting of the ensuing chaos.
For those unfamiliar with Flynn, he is an award-winning actor, writer, producer, host, and comedian.
His career began on the soccer field before he transitioned to stand-up, winning the prestigious Boston Comedy Riot.
Since then, he has made numerous appearances in film and television. He played The Wedding Coordinator in The Heartbreak Kid with Ben Stiller, appeared alongside Jim Carrey in Me, Myself & Irene, starred in Osmosis Jones with Bill Murray, and portrayed Charlotte’s boyfriend Bram Walker in Sex and the City. A character voted one of the series’ most popular.
Recently, he landed roles in The World’s Greatest Beer Run with Russell Crowe and Zac Efron.
Live, Flynn’s humour is often dark but never mean-spirited. He mines his own life, family dysfunction, awkward moments, and the absurdities of modern existence for comedy, delivering it with brutal honesty that is both uncomfortable and side-splitting.
His ability to uncover humour in the most unlikely places is where his true genius lies. From childhood trauma to the absurdities of social media, his sharp observations cut through the noise.
Demonstrating that he had done his homework on Kiwi culture, Flynn incorporated a rugby-themed sketch into his set.
His routine touched on infamous rugby league player John Hopoate and his on-field antics, culminating in a punchline about the New Zealand Cancer Society using Hopoate’s image to encourage prostate exams.
What truly sets Flynn apart is his improvisational skill. While many comics stick to a formulaic setup and punchline, Flynn thrives in unpredictability. In an impromptu riff on yoga and the plow position, he seemed to be arguing with himself, sorting through everyday annoyances while sending the audience into fits of laughter. The more absurd the thought, the louder the response.
Flynn also excels at turning discomfort into comedic gold.
He fearlessly dives into topics many comedians would avoid. Health, race, and relationships, without sugar coating them. Instead, he brings the audience into the experience, allowing them to laugh at things they never expected to find funny.
That said, his set isn’t all heavy. His ability to switch from highbrow humour to lowbrow gags in a single breath makes him unpredictable and hilarious.
Like many comics, Flynn mixes fresh material with classic bits, including his well-known School of Modelling skit, which I first saw in a TED Talk back in 2013.
The 2025 version has evolved, enhanced by Flynn’s exaggerated facial expressions and almost contortionist body movements. Even for those familiar with the bit, it felt fresh and even funnier than before.
Seeing Flynn live is undoubtedly the best way to experience his comedy. His presence, timing, and physicality add layers that no recorded performance could capture. The audience was fully engaged, soaking up every moment, until an unexpected flashing light from the promoter at the sound desk signalled Flynn to wrap up. Even Flynn seemed surprised that his time had been cut short.
He closed with a brilliant bit about his younger sister Kelly holding a block party for when he first appeared on Sex and the City, showcasing a rare vulnerability that felt more like a genuine reflection than a punchline. It was a fitting end to a set that left the crowd both exhausted and deeply satisfied.
He’s exposing the absurdity of life while making us laugh harder than we have in ages. His set is a reminder of why we go to comedy clubs in the first place. To embrace the chaos of the world and laugh at it together. For Kevin Flynn, chaos is the joke, and we’re all in on it.
Paul Marshall