There’s something deeply good for my soul to sit in a buzzy room with a bunch of like-minded strangers while someone on stage does their best to make us all laugh.
Whether it’s giggling at ourselves and our common curious habits and failings, chuckling over a sharp take on the state of the world and our politicians, or just guffawing at someone physically making a fool of themselves, laughter is the perfect panacea to the doom and gloom of the day’s headlines.
I certainly felt a mood reset as I walked out of the Factory Theatre on Wednesday night after seeing Tom Sainsbury’s sold-out show Lessons Not Learnt as part of the Sydney Comedy Festival.
The main space at the Factory Theatre was full of his self-described “gals” – his loyal and biggest demographic of women aged 45-60 of which I am proudly and firmly part of – who first found him on Instagram where so many of today’s comedians get their start and find their following.
Sainsbury took the crowd on a hilarious tour through the workings of his mind and some of his most embarrassing moments for 55 minutes (he kept time). Those of us who left wanting more got it – the Kiwi comedian did a little “meet-and-greet” downstairs and posed for selfies before his second gig of the night.
It was the first Sydney Comedy Festival show I’ve managed to get to, but it won’t be my last. We’re not even halfway through the Festival, which runs until Sunday, May 17, and there’s plenty more in the program that’s worth it.
The big names still to come
Part of the fun of a comedy festival for me is taking a punt and seeing someone you’ve never heard of and discovering your next favourite comedian. But the Sydney Comedy Festival also draws in international stars that you should add to your hit list if you can.
First up, Tiffany Haddish is in town for her only two Australian shows this weekend, at the State Theatre on April 25 and Enmore Theatre on April 26. There are tickets left to both shows to see this force-of-nature performer.
Then there’s Jimmy Carr, bringing his Laughs Funny (which he most certainly does) tour to the Darling Harbour Theatre on Sunday May 10. His stand-up shows are packed with literally hundreds of one-liners, some of which may offend, but on a cost-per-joke basis, the English comedian provides excellent value for money.
Also worth checking out: Stephen K Amos, Daniel Sloss, Joanne McNally, Celia Pacquola, the gloriously unfiltered Reuben Kaye plus more.
Next on my list: Kyla Cobbler at the Enmore Theatre
The other ticket to a Sydney Comedy Festival show that I’m clutching is for Kyla Cobbler: Gone Rogue, another comedian I’ve discovered – and become a devoted fan of – through Instagram.
The Cork-born comic has racked up close to 700,000 Instagram followers and 100 million-plus video views in just four years on the circuit. She speaks to the same demographic as Sainsbury’s “gals” mainly because she celebrates them. Gone Rogue covers the chaos of Barcelona dating life, the unpredictability of friend crushes, and the tactical warfare of the suburban barbecue.
I’m seeing her at the Enmore Theatre on Friday 24 April but she’s also performing at the State Theatre on May 13.
Make a night of it
One of the genuine pleasures of the Sydney Comedy Festival is that the theatres are little entertainment hubs in their own right.
This makes a compelling case for extending your night to include dinner or a drink, before or after a show. Or both!
Enmore Road is rocking these days after being designated a “special entertainment precinct”. Around the Enmore Theatre, I love Jacoby’s Tiki Bay for a pina colada, Fortunate Son for a more elevated cocktail or wander down to Bar Planet for one of their signature martinis. There are 13 Comedy Festival hubs and we’ve rounded up so places to eat and drink around each and every one.
So if you or a friend has found yourself uttering the phrase, “I could do with a laugh”, there’s still plenty of fun to be found in the Sydney Comedy Festival program and now is the time to book. It runs until Sunday, May 17, 2026, and shows are available across the city for a wide range of costs.
To book, go to sydneycomedyfestival.com.au
