“For every dream you’re denied, that’s one thing, but for every dream that’s available to you, it is also a dream you probably won’t achieve. Which is the experience of humanity – at least you have a shot at it.”

For comedian Titus O’Reily, that is one of the most underrated narratives to come out of the advent of the AFLW. Young women have the opportunity now to “grow up to realise they’re not good enough to play footy”. An equal opportunity … to fail.

O’Reily has recently come off a successful run at the Melbourne international comedy festival and has been experiencing a boom in his sports comedy career much like the growing AFLW code. With two books, two comedy festival runs, tours, a popular podcast and a sizeable social media following, O’Reily has fast become a staple in the sports comedy scene.

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What sets O’Reily’s work apart from others is that he does not just push boundaries to encourage conversation about sport in a cultural and political way. He brings in historical precedents, holds organisations accountable and is one of the few comedians who also extends his nuanced comedy to women in sport, particularly the AFLW, despite knowing it angers some of his followers.

“I find it funny that people get so angry about it because, even if you have no interest in AFLW, it’s not compulsory to watch it. It has no impact on your life in any way. You might have to catch an ad for it on TV, but you know, I have to catch ads for Married at First Sight on TV. It doesn’t mean I’m going to go off tap about it.”

Unsatisfied in a corporate career, O’Reily got his start in the satire game when a group of friends decided to create a website where they could write about sport. “I thought I’d do it for two weeks and get bored,” he says.

It was after a piece he wrote about the fear of raising a Carlton supporter gained some traction, that he considered the possibilities this kind of writing could lead to.

“It was still very much a hobby. Some people play golf on the weekend; I would write and start to tweet. And then it started to grow and I got more into it. The others dropped off and I grabbed my own site and then it kept growing. It got to a point where I thought, this could be something.”

Over the last few years, O’Reily has worked at building his sports satire brand through social media. His Twitter following currently sits at 227,000. These numbers are now translating into new opportunities and platforms for his style of comedy.

“I was kind of in an interesting spot because I was writing satire, and because I was writing fairly fearlessly,” he says. “The point of satire is that you’re not just writing puff pieces.”

Being satirical in such an inner-sanctum space can have its drawbacks. “The AFL and AFL community – including the media, the players, the clubs – is a pretty tight-knit community. You can criticise certain things, but if you’re too critical, people are wary of you. So in the early days, I was really cut off from that and no one would hire me either.”

Despite his growing success, O’Reily still uses his fan mentality to connect himself to his satire, which means regularly commenting on his own plight as a long-suffering Melbourne supporter.

Titus O'Reily (@TitusOReily) Reflecting on last night’s defeat and I realised I haven’t been this sad since the vast majority of my life. #AFLDeesDons

“I’ve always thought from the fan’s perspective because I’ve come from outside of that [AFL industry] bubble and because I’m doing satire. I think satire is basically pointing out the difference of what people say and what they do. And sometimes it’s a power thing, but it doesn’t have to always be. There’s this thing in comedy that you should never kick down, which I don’t believe at all.

“I don’t think you should kick down for the sake of kicking down, but there are times when non-powerful people are doing horrible things, like people who post racist things on Facebook. Are we not going to make fun of them because they’re not in positions of power? So it depends what you mean by always kick up and not down.”

It is perhaps this approach that allows him to give a comedic voice to the social and political side of sport.

“I look at people like Clarke and Dawe, and John Clarke used to do this: the comedy is the sugar that makes the medicine go down. So if you just write, ‘People who boo Adam Goodes are racist’, that comes across as preachy and it’s not funny. There’s nothing to make people feel like, even if they agree, that they want to share it. With humour, you can point out things that people think, and it has a slightly different impact even if you are saying the same thing.”

Which is not to say that O’Reily doesn’t also take some hard lines when it comes to the big issues in sport. He is aware, however, that his interactions on social media in these instances are not the same for everyone when they add their voice to these conversations.

Titus O'Reily (@TitusOReily) This image annoys the sort of people worth annoying. https://t.co/IaJz2FZRfp

“It’s interesting, when you’re a white man doing this on social media, when you do stick up for things like the Tayla Harris photo, you get all these congratulations, and I’m aware of that. I don’t do it for that reason but I find it funny where I’m more likely to get people saying, ‘Good on you for standing up for this’, like you’re some hero, when I see 50 other women write the same thing and they get told to shut up.” Or worse.

Yet O’Reily enjoys being an agitator in this space and won’t let social media trolls dictate his comedy. “I do get a perverse enjoyment about annoying the people who get annoyed by AFLW,” he says. “I like challenging a way of thinking.”