Two times Archibald finalist Vanessa Stockard is in demand with upcoming exhibitions and a residency in France. The Bowral artist tells MELISSA PENN how diverse subject matter feeds her art, from flowers and her toddler to the imagined life of a vagrant called Derek Milkwood.

Vanessa Stockard is one of those people who laughs loudly and often. This is a good thing because much of the inspiration for her quirky, often ethereal abstract, still life and portrait paintings comes from observing the funny side of life.

“People are bizarre and funny and I love it,” says Vanessa, 42, a dual Art Gallery of NSW Archibald Prize finalist. “[Husband] Will and I go into town and things happen that might make other people mad, but we just laugh. I’ve been on the lookout for absurdity for a long time because I have an anxiety disorder that comes with depression. Seeing the hilarious side of life helps me feel better. It’s part of my personality and now my paintings.”

Combining a sense of the ridiculous with thoughtful subject matter, Vanessa began a series of paintings 18 months ago featuring Derek Milkwood, a fictional character based on a naked vagrant man who used to frequent bushland near where she lived in Glebe. “I’d played around with a Derek character for a while but it wasn’t until I started the series that I realised I could go anywhere with it,” she says.

“I’ll see something weird or crazy and think, I have to make a Derek out of that. I use him as a platform to discuss social issues, to explore what it’s like to see the world so differently that you don’t know you have to wear clothes in public. It was an interesting experiment that’s turned into something I’m now addicted to.”

Her Derek Milkwood paintings took centre stage in a solo exhibition in Hong Kong in May, but Vanessa’s other work is also garnering a lot of attention. She was part of four group shows around Australia in June, and she will be the featured artist at Visual Arts in the Valley in Kangaroo Valley from September 28 to October 1. “There’ll be an exhibition room of my paintings as well as a virtual presentation of me working and talking,” she says.

In November she’ll be part of a group show in Miami, and from October until March 2019 she’ll exhibit alongside artist Euan Macleod at Sydney law firm Clayton Utz as part of 3:33 Art Projects and the Clayton Utz Art Partnership. “I’m really excited about being selected – it’s a huge break for me career-wise,” she says.

For the past two years, Vanessa’s self-portraits have been chosen as finalists in the Archibald Prize. This year, 21 out of 58 finalists were self-portraits, leading some critics to point to a “culture of selfies”. “I think the Archibald is changing in terms of what is considered a better painting rather than which famous person is painted,” says Vanessa.

“I do a bunch of self-portraits at a time. Out of 10 that I might do, the first is rubbish and probably only number three and seven are any good. The third has something – it’s still a bit clumsy. At seven you’re experimenting. At 10 it’s too slick and doesn’t resonate much personality.”

We’re talking in the rustic timber kitchen of the Bowral home Vanessa shares with her husband, videographer Will Wolfenden, and their two-a-half-year-old daughter Isobel. Set on two hectares, it’s Moroccan/medieval in style, with thick wooden beams, cavernous rooms and sandstone fireplaces. Will designed the house while in hospital recovering from an operation and helped build it over nine months.

“In 2016 when we moved in I was breastfeeding so I pretty much lived in this room,” says Vanessa. “It’s about the same size as our previous entire house. For a long time, the rest of the house felt like another planet.” The kitchen windows look across bushland to Vanessa’s “blueberry cupcake coloured” studio where she paints five days a week and sometimes on weekends.

“I get up at 6am to have some time by myself, then I’m in my studio by 9am,” says Vanessa, who paints in oil or acrylic directly on board or canvas. “When I’m there I can focus. I hate anyone else coming in. We tag team with Isobel on the weekends. Will’s against the idea of me working too much but it keeps me sane. There are only so many Wiggles songs I can take.”

Vanessa and Will moved to an 1850s sandstone cottage in Mittagong from inner city Sydney six years ago, seeking space and serenity. Having her own place to work has helped Vanessa expand creatively. “In Sydney I worked at the kitchen bench. Now that I’m here, it’s a bit like what happens to a goldfish. If you give it a tiny bowl it stays tiny but if you give it a bigger space it grows.”

Isobel has also become part of Vanessa’s diverse subject matter. Painting is a way to record her growing and changing, she says. “Sometimes I paint from photos of her; other times I paint the experience of her and they’re a bit cartoonish in their nature. Kids are so bizarre and hilarious – it’s magical watching them grow. I have about 20 paintings of her that I won’t let go. I don’t want to forget the funny things she did at each age, like holding her head when she was learning to walk.”

Vanessa spent her own childhood growing up on acreage on the mid-north coast of NSW. She had an artistic mother, a father who was a dentist with an interest in textile art, and a grandmother who was a painter. Art appreciation was part of life, says Vanessa, who loved drawing as a child. After finishing boarding school in Sydney she began an arts degree in maths, chemistry and fine arts at Sydney University before switching to the UNSW College of Fine Arts or “COFA”.

“I couldn’t stay awake in the maths and chemistry lectures and realised I didn’t want to do any more academic stuff. But it was only when I was finishing at COFA that I decided to be a full-time artist. Even though it took me years to get a show – I had three jobs, nannying, working in bars – I always described myself as a painter because I always painted.”

Major influences were a “weird combination” of Australian landscape painter Fred Williams, 16th century Spanish artist Diego Velazquez and American pop surrealist Mark Ryden. “I thought it was ground-breaking the way Fred Williams saw the landscape; completely outlandish that you could just do it like that. I loved that he got the paint tubes and made messes on great big beautiful flat landscape panels. And the landscape looks exactly like that.

“I’ve always loved the optical tricks about painting, where your mind forms a picture for you,” she adds. “Look up close and you’ll see something so abstract it looks like an accidental smudge. But step back and your mind will make something that almost looks photo realistic. There’s a bit of magic to painting and I love that.”

In September, Vanessa will take up a two-week artist-in-residence position at Chateau D’Orquevaux in France, accompanied by Will and Isobel. “I can’t wait. You need to leave your house and have culturally different experiences. Because as hilarious and bizarre and magical as being a mum is, you need to expose yourself to new things. Otherwise I’ll bore everyone to death. They’ll be saying, ‘Not another baby painting’.”

With the rich imagination and broad subject matter that Vanessa draws on, this seems unlikely. She doesn’t even create works thematically for upcoming exhibitions. Rather, she sets aside pieces that she thinks will fit together as she goes.

“I’m an obsessive worker. I tend to focus on one thing at a time for six weeks max and then I’m done. Generally I paint flowers when I don’t have anything to say but I still want to paint. I do them as a practice because it’s fun and I find it fairly easy. It’s like my breathing time until something weird happens and I’ll be back on that train.”