Permission to Play
Multidisciplinary artist Cassidy Jackson on Basquiat, flow states and why being called naive was the best compliment she’s had.
Cassidy Jackson doesn’t remember much of life before drawing. She was in early primary school when she first picked up a paintbrush, in a household where making things was always encouraged. “It was just something that came really naturally to me,” she says. Today, the multidisciplinary artist moves between painting, yoga and acting, and is Ovolo Sydney’s artist in residence for the latest chapter of our Outliers series.
When asked about her favourite artist of all time, Cassidy beamingly responded with Jean-Michel Basquiat, highlighting the neo-expressionist, childlike playfulness in his work. “It feels like a stream of consciousness rather than anything that’s super curated, and I really try to embody that in my own practice.”
That instinct once earned her an unusual compliment. “Someone once told me that my artwork was naive. At first I was like, ‘Is that a compliment?’” It was. The woman explained that she saw freedom, playfulness and a childlike element in the work. “It made me feel like my work was coming from a place of just wanting to play and be a kid.”
For Cassidy, being an outlier means creating from your own authenticity, staying curious and refusing to be put in a box. Her advice to young artists is simple: trust yourself. “Especially living in this age of AI and algorithms, there’s a lot of pressure on people to do things a certain way. Sometimes the noise can get quite loud, and I think it’s good to listen to your own intuition.”
Painting, yoga and acting, she says, are three practices that feed one another. “They all require a deep level of presence,” and moving between them keeps her work fresh.
Presence is something hotels trade in, too. “Artwork in hotels works beautifully because it’s a form of escape,” Cassidy says. “When you go to a hotel, you kind of want to feel like you’re somewhere else.” Her residency gives her room to explore her own idea of Sydney’s heritage and energy, on a wharf built in 1915 at the height of Australia’s wool trade and now in the middle of its own transformation. “It’s really cool to know that so many people will get to experience the work and connect with it in their own way.”
She runs on a long black by day and a dirty martini by night, and her plans are anything but modest. In five years, Cassidy wants to be exhibiting internationally, her practice still evolving and expanding. What matters most, though, is harder to measure: “I would like to be known for making people feel something. Creating work that stays with people is really important to me.”
On Finger Wharf, that work has found its ideal audience: guests who came looking to feel somewhere else. See it for yourself at Ovolo Sydney.