Wil Anderson is worried he has wasted his life. The man with several high-profile jobs across TV, writing, producing and podcasting says he hasn’t squandered it entirely. But he thinks he might have wasted time doing things that were good for his career, “but not necessarily good for my creative self”.

“It’s a major regret in my life that my creative self had small ambitions about what I wanted to do; my creative self wanted to do a show at the Melbourne Comedy Festival,” he says. He has of course done that, appearing in the festival numerous times over the past 25 years (and he has a swag of awards to prove it – a Helpmann, numerous MCIF People’s Choice awards… the list goes on).

“But the thing that I purport to be most passionate about is comedy, right? And in 25 years, I’ve never tried doing it full-time!” While most stand-up comedians will perform a show hundreds of times, other things - including a trio of ABC panel shows - have tended to get in Anderson’s way.

At 26, he landed a job as co-anchor of Triple J’s breakfast show, and shortly after became the host on The Glass House. Then came the advertising discussion show Gruen (originally called The Gruen Transfer), and now he also hosts Question Everything.

“Things just kept going,” he says. “So I’ve done comedy shows in that time, but often I only perform them 30 or 40 times.”

Only?

“Well, if you look at something like Nanette, I think Hannah (Gadsby) had done that show 250 times before she recorded it. Most people will have done their show hundreds of times.”

Every year Anderson considers a return to full-time stand-up, but then more projects come along. This year, he’s hoping to change his pattern – he’s taking his new show on his biggest tour in five years, performing across Australia and, hopefully, internationally.

Where many an older comedian might baulk at the idea of all that time on the road, Anderson loves it; being 50 has definitely not wearied him. He used to be able to perform a show 300 times “back in the day”, even juggling his other gigs. “I’d like to do this show 150 times.”

Yes, he says, he does get sick of the sound of his own voice. “Oh, always. But I have no other skills.” He’s good with a pun though - this year he’s broken out his “Wil” pun for the 29th time. Although perhaps he should have thought the new show title through. Wilegitimate seems like harmless Anderson wordplay – except that the show is built around something he discovered last year about his dad.

“I need to point out that it was named that before I found out the thing about my dad,” he says. “They are definitely not connected to each other! I don’t want to give people the wrong idea.”

He’s not giving any spoilers, just that it’s something he discovered after organising a present for his dad’s 80th birthday. “He’s a dairy farmer who doesn’t drink, doesn’t smoke – you can’t even buy him cigars or brews, you know? So my brother and my sister and I were trying to think, what do we get this guy who’s impossible to buy for?”

Anderson senior is a fan of sports broadcaster Mark Howard’s podcast The Howie Games, on which he interviews big-name sports personalities. Anderson’s dad “ doesn’t know how to download a podcast, but my mum does it for him and then he listens to it like it’s the radio”.

Anderson, a mate of Howard’s from high school, came up with the idea of the broadcaster interviewing his dad, podcast-style. “We brought him to the studio and he recorded this hour-and-a-half interview about his life. It was brilliant,” he says. “He talked to Mark about things in a way that he wouldn’t talk to the family.” Which is how Anderson discovered something he’d never known about his dad.

“The thing itself isn’t really that important. It’s about how amazing it is to discover this thing.” A thing, he elaborates, that should have been obvious. “It’s like a murder mystery where everybody else has spotted who the killer is. It’s not salacious – but it’s great material.”

Anderson always looks for a theme, and the conceit of his discovery about his dad is a “sensational hook”, the concept of which also feeds into some of the things he’ll discuss.

“The show is actually an exploration of the limits of that stuff. Everything, even comedy, is about getting attention straight away now,” he says. “Then there’s the Netflix-ication of it, which is you need to have something in that first minute that hooks people to keep watching. People really are doing that and readjusting how they work. So the show really is about how limited an approach that sort of clickbait headline style is.”

Anderson, who studied journalism at Canberra Uni (graduating top of his class in 1995), despairs at the rise of clickbait.

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“It used to be that the big letters at the top of the article told you something about the smaller letters underneath,” he says. “Now often it’s the complete opposite. And because everyone is competing for our attention, there’s been an escalation in needing to be more and more provocative.”

He gives an example: “If I was like, ‘Tom Gleeson is not hard, he’s actually soft’, Tom Gleeson then has to come out and escalate whatever it is and then, it’s like, ‘what are we doing?’ Where we’d once read a newspaper in the morning and perhaps watch a news bulletin at night, now we’re bombarded with news – and non-news – all the time.

“Getting updated once a day felt about right, then suddenly there was this 24-7 news cycle. And now the 24-second news cycle – everyone’s a broadcaster, everyone on TikTok’s got an opinion about things and … it’s full-on, isn’t it?”

Anderson can talk passionately at length about, it seems, everything, and over the course of an hour and a half, we cover everything from AI to his osteoarthritis (the two most effective treatments are also “the most boring - losing weight and stopping alcohol”).

His theory about the rise of AI is that “we always get sold on what the upsides of things are, and there will be some upsides with AI, but the idea that it will be used mostly in a good way is just ridiculous”.

On the topic of comedy, he’s happy to nurture emerging comics on Question Everything, because “it means the first time they walk into a TV studio, they’re not overwhelmed” but rejects the idea of comedians being hobbled by censorship.

“Is that the biggest bullshit you’ve heard in your entire life?” he says. “And the people saying it, the Ricky Gervaises and the Dave Chappelles, are the most successful comedians in the world. Ricky Gervais was the highest-selling comedy tour of last year – that says to me that you absolutely can say whatever it is that you want to say, and him complaining? It’s a marketing tool.”

Using the “anti-woke” stance has become an established business model, Anderson says. Perhaps a new career move for him? “Well, when you’re like me, a middle-aged white man, there’s an argument that (doing) that would be a smart career move,” he says.

“Perhaps I could Joe Rogan it up and make that pivot to a libertarian alt-right view of the world. It would be lucrative…”

Wilegitimate is at Melbourne’s Comedy Theatre until April 21, for the Melbourne International Comedy Festival http://comedyfestival.com.au; Brisbane Comedy Festival, May 3-5; and the Sydney Comedy Festival, May 10-11. For full tour details check comedy.com.au