But Do's latest project sees the funnyman take on a whole new role as a portrait painter and probing interviewer.

Hand-picking eight Australians he admires to paint and interrogate in ABC series Anh's Brush with Fame, Do's disarming ability to crack his subjects wide-open is one of the biggest revelations of the series.

"I've always been a serious person," the 39-year-old says. "If you listen to the questions I ask in the series, they're always, 'take me back there, what was that like?'. Not everyone asks you that, you know, in life.

"I've always been like that. I don't like small talk. If you're up for a big conversation about life, death and your greatest joy and deepest regret, let's get into it."

Multi-talented, Do authored critically-acclaimed memoir The Happiest Refugee in 2010 and took up painting about six years ago following the death of a close friend. Do's haunting portrait of his father was a finalist in the 2014 Archibald Prize.

Jimmy Barnes, Kyle Sandilands, Kate Ceberano, Amanda Keller, Magda Szubanski, Craig McLachlan, Anthony Mundine and neurosurgeon Dr Charlie Teo were all selected to be part of the series.

In an intimate studio in Sydney, Do paints his subjects over a two- to four-hour sitting as he probes them about their crushing failures and greatest accomplishments.

"It's incredibly intimate. Because there's no studio audience, the guest doesn't feel like they need to perform. They can let their guard down and just be really authentic.

"I think that's one of the elements that makes the show so compelling, the guests share so much of themselves that they don't often share."

But what's arguably the most compelling part of the series is Do's ability to dive headfirst into uncomfortable topics.

During his first session with author and comedian Magda Szubanski​, Do asks Szubanksi about her sexuality, her difficult relationship with her father and her struggle with depression.

"Anh is strangely disarming," Szubanksi says later. "He just asks these simple questions that kind of just peel you open."

Many revelations come from the series. Rocker Jimmy Barnes reveals the moment an unknown daughter he fathered at 17 shows up at one of his gigs. Radio host Kyle Sandilands reveals how the sound of the radio would keep him company when he was homeless and sleeping behind petrol stations.

"The guests either had to be someone I love or admire or someone I find fascinating. A bloke like Kyle Sandilands, he's never boring," Do says.

"He told me that when he was homeless and he was sleeping behind a service station, at night time he'd listen to the radio that was coming through the bowsers. He'd love the voices that came through because they were his human company. That's when he fell in love with radio.

"The guests are really so generous and I like to think that I don't judge my guests when I ask them a question. I think that allows them to tell me whatever they want."

The paintings are organic and develop throughout the sitting. For Szubanski, Do depicts her as a survivor, a Wonder Woman figure with flowing hair. "I really want to give this painting a sense of triumph," Do tells Szubanksi.

Inevitably, there comes the moment of truth at the end of each episode when Do has to reveal the subject's portrait. Will they like his version of them?

The answer is no, not always. Do likens it to being a MasterChef contestant who plates up their food, heart and dreams to the panel of judges at the end of each challenge.

"I've been saying I don't care in interviews but you know what, I do care. But the painting is just a fun part of the show. Like when you're watching Antiques Roadshow and you're hanging out for the price of the watch like, 'What's it worth?!'

"You don't really care but you're interested in the reaction of the guests when they see the painting. It's a fun finish to the show, but it's really not the point of the show."

For the record, Szubanksi loved her portrait.

So what next for the happiest refugee? Do says he's happy juggling a career in comedy, painting and television and is planning another comedy tour. He'd also love the chance to do a second season of Anh's Brush with Fame.

"I love doing all those things. People go, 'Mate, how do you do so much stuff?' I can honestly do all those things as hobbies. If I inherited a billion dollars and didn't have to work ever again, what would I do to fill my day? I'd paint, I'd write jokes and stories, and I'd hang out and chat to very interesting people."