Interview: Ray O’Leary on A Pessimist’s Guide to Optimism

Ray O’Leary has a show in the 2017 New Zealand International Comedy Festival called A Pessimist’s Guide to Optimism which you can get tickets to here:

Who are you and how did you get started in comedy?

I’m Ray O’Leary, 24 year old stand-up comedian and 2017 Billy T Nominee.
For years I wanted to do stand-up comedy. It started when I was 13 and saw a special of Ellen DeGeneres, then it went away and came back when I was about 20. I never signed up for an open mic because I was scared of not being funny and embarrassing myself in public. Me and my friends used to go and see stand-up every Wednesday in Wellington at a great show called the Medicine and they could tell I wanted to sign up and encouraged me to, but I was always too scared. I started making excuses like ‘I need to work on uni stuff’, and then it was ‘works really busy right now’. When I realised work was never going to stop being busy and that I hated waking up early in the morning, I finally signed up to the Raw Meat Monday open mic at 22. I regret waiting so long cause that’s 2 years I could have been practicing.

What inspired your Comedy Fest show?

It’s called “A Pessimist’s Guide to Optimism” because I think I’m a naturally pessimistic guy. But I studied philosophy so I’m really interested in morality and doing the right thing, and using my comedy to talk about important issues facing society (like Jon Oliver in Last Week Tonight). So hopefully I’ll solve all the world’s problems, or at least get people thinking about them so we can feel optimistic about the future.

What’s it like being a Billy T nominee?

The award is judged on how good your Comedy Fest show is and I feel a lot of pressure about writing the show, but I think the award has been good because it’s given me a lot of opportunities I wouldn’t have gotten otherwise. It’s also like a seal of approval so audiences know my comedy hasn’t reached its best before date.

Why should people go and see your Comedy Fest show?

I might save all of the world’s problems, and you wouldn’t want to be the only one who didn’t know the answers would you?

If you could describe your fest show in 3 words what would they be?

Philosophical, intelligent humour


What’s your favourite part about the NZ Comedy Fest?

It’d have to be the drinks once the shows have ended, where you unwind with the other comedians and just joke around. You get to meet all these great comics from around the world after watching them do these amazing shows.

What’s the most important thing to you about doing comedy?

I like that you’re given a platform to speak in front of large groups of people. I think it’s really important to use (some of) that time to get people to think about important societal or political issues. It’s a double-edged sword though because your fans just end up being people who agree with you and you start preaching to the choir.

What advice would you give to someone wanting to get into comedy?

The thing that stopped me from doing comedy was fear of public embarrassment. So when I finally got to the point where I was willing to sign up to an open mic, I didn’t tell anyone I knew. I was scared they’d all see me bomb. So I was going out to open mics twice a week in secret and telling my flatmates it was because my friends were having various emotional crises that I was helping them with. If this excuse won’t work for you, I’d recommend making more emotionally unstable friends.

Once you’ve switched on incognito mode, and prepared your jokes, you just have to realise it’s just a bunch of strangers in a bar. Who cares if they don’t find you funny? They’ll forget about you. And if it goes well, it’ll feel amazing.

Aside from your own, what are three comedy fest shows people should go and see?

If you can, check out comedians who you like the sound of but don’t see on tv. You don’t get Seinfeld’s or Degeneres’ without people supporting them in the beginning. I’d recommend checking out these excellent comedians:

Lucy Roche – Dollars and Sex –

Ben MacGougan – Magical Foot Job –

Joel Hansby & Josh Davies – Dorkward –

Check out Ray O’Leary’s Facebook here:

And follow him on Twitter here:

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s