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  • Writer's pictureJenny Wynter

Meeting Bill Bailey: My Comedic Mentor de Awesome

I was oohing and aahing (that’s right, I never ‘um’) over whether to even post about this, namely because it just seems to damn uncool/starstruck/completely and utterly daggy to do so.

BUT…I simply cannot contain this incredible excitement inside.

The fact is, I’m not one of those cool people who can be all aloof at meeting one of their all-time heroes. I wish I could be, but I’m just not.

So here tis, in all its resplendent, unabashed dagginess.

You know how sometimes you’ll do that whole ‘who are the top five people you wanna meet in the world?’ thing? (Please, dear heavens, tell me it’s not just me…) Well, number one on mine has – for the past 5+ years – been Bill Bailey.

I kid you not.

Namely because nobody on Planet Earth, living or dead, has influenced my comedy more than him. The first time I saw “Part Troll”, I felt the earth move.

At the time I was just starting to build a bit of a profile in the Brissie comedy scene, but when I saw that show…it was like a beautiful little nymph tapped me on the shoulder and whispered mildly violently (but it felt good) into my ear: “Aha! This! This! This! This is what you want to do!”

So to actually connect with the man himself – in the flesh – well, you know…I just can’t NOT write about that.

So here goes.

As I find myself typing this, buzzing and thinking ‘how the heck did this actually happen?’ let me backtrack six months or so to Woodford Folk Festival, for that is where this all began.

There I was, supervising littlest dude playing in the Kids’ Festival sandpit, when it became apparent that he had struck up a rather cute friendship with two twin baby boys.

Thus, I really have my son to thank for this entire story. My then 10 month old son.

But first, back to Woodford. To surmise:

  1. boy meets boys;

  2. boy gets along swimmingly with boys;

  3. mums get a-chatting’

  4. mums hit it off like a house on fire;

  5. mums realise they live only five minutes’ drive from each other;

  6. mums swap phone numbers and walk away into the sunset with promises of playdates floating on the breeze.

In other words, a potentially beautiful friendship is born.

(Note: my hubby will point out that he started chatting to said mama first, and thus HE is responsible for this chain of events, but it just doesn’t read quite as well that way. So let’s just move on, with the truth at our heels like the wind at Superman’s cape.)

A couple of nights later, the mother in question and I bump into each other again, but this time I’ll all dolled up.

“Look at you!” she says. “What are you all glammed up for?”

“Oh, I’m performing tonight, you should come!”

“Oh, no, I’d love to but we can’t, we’re off first thing in the morning and I’ve got to get the twins to bed. I didn’t know you were performing here!” she says.

“Yeah, I’m a comedian!”

“Are you really?” she says. “Wow! You know, I went to school back in England with a comedian, I don’t know if you’ve heard of him…”

insert dramatic pause here

“…Bill Bailey?”

I do believe the entire Woodford Folk Festival site felt a tremor measuring about 8.4, this being my jaw hitting the hippiefied earth.

“Oh, you know, I’ve heard of him I guess, he’s only like my favourite comedian on the entire PLANET!”

And with that, she proceeds to tell me that she’s still in touch with her childhood friend, that he used to play funny songs for entertainment at parties – including her own 18th! – and that whenever he comes to Australia on tour they catch up.

Cut to a couple of months – and several playdates – later, when my friend sends me a text that reads: “Bill is coming in July! Will see if I can get some tix!”

A small part of me floats off to a higher realm.

And that, dear friends, brings us to this Sunday night just gone.

There we were. Dressed and psyching up to to go tick another box off the bucket list: seeing Bill Bailey live AND meeting him afterwards! (Hopefully also live.)

The show was amazing. As expected. He did about 15 thousand encores, half of which happened as a genuine surprise once most of the crowd had left the building! I just dug that so much, as did the remaining audience members; just knowing that he didn’t HAVE to come back out, but just did because he WANTED to. Loverly.

And then, once it was all said and done….we headed to the  greenroom.

Now I must say that as excited as I was about meeting my comedic mentor/inspiration #1, I’d also spent the better part of the past week trying to psyche myself down for it. That is, to not get my hopes up too high of what could happen (you know, ridding myself of dreams of the “he’ll pronounce you the chosen one!” variety) and just being prepared that in reality our introduction would most likely happen more like:  “Hi, nice to meet you!” followed quickly by “Well, I’m really exhausted and off to the hotel now, see you!”

The reality of how things turned out is really hard to wrap my head around…

We walked into the dressing room – a daunting sight for Bill, I’m sure, with his childhood friend, followed by five other adoring women descending on his headquarters – and took turns introducing ourselves.

Even still, over-run with company, I’m really, really happy to say that he was nothing less than completely friendly and super hospitable, offering us wine, nibblies, beers, whatever was in the room short of the mirrors. As I think I’ve mentioned before on this blog, I really love it when somebody you look up to in the public eye actually turns out to be a nice human being. I think I actually felt relieved!

We all sat down and chatted – about his time in Coober Pedy (he showed us some incredible photos of the underground hotel, houses and shots from the air), his dogs, his family…all the time I was trying to just hold my shizz together, and not devolve into a slobbering amoeba, for fear that security would kick me out for not having the required minimum grasp on reality.

After half an hour or so, Hatty mentioned her proposed plan for the following day: she would take him to Australia Zoo, after which I would meet them at the beach to hang out, then would drive him back to Brisbane for his gig.

“Oh really?” he turned to me. “That’s very nice but I have a driver, you really don’t need to put yourself out,” he said.

“Oh no, I’d be totally happy to,” I said, then… “I have a bit of a confession to make…”

“I’m a comedian too, I do musical comedy and I don’t want to be all gushy but you’ve really inspired me so much…”

All the women in the room went “awwww.”

No, I mean literally. They went “awwww.” It actually made me feel supported and a bit like I was on some sort of bizarre comedic dating show.

“Oh, well that’s very nice, thank you,” he said. “Well if you’re sure, I mean I’m sure my driver would be happy to have the afternoon off!”

Our mutual friend then mentioned that I was going to New York for the improv masterclass, so we spoke a bit about that and what I’d been doing in Canada. We talked Edinburgh Fest, Just for Laughs, then Melbourne Comedy Fest – and I told him how the plan this year to take my show to Melbourne was derailed by the car crash.

“Hmmm,” he said. “Have you thought about doing Edinburgh?”

“It’s funny you should say that!” I said (oh, if he only had a dollar for every time he’s heard that…hehe)  “I’ve been thinking about it a lot lately – seeing as it’s so much work already just taking the show to Melbourne with the family – maybe I should just go for it and go straight to Edinburgh.”

The ladies all but cheered whispers of encouragement: “Yeah you should! Just do it! Go on!” Actually in hindsight it was kinda like a very small circle of Oprah angels, surrounded by an all-knowing wizard with a British accent.

“Well,” Bill said, “I’d certainly be very happy to do what I can to help you out.”


I still, to this moment, even typing this, cannot believe that moment actually happened.

I even tossed and turned the next day wondering whether to call my grandma to let her know – on the one hand, I knew she’d be super excited, but on the other hand knew that her genuine pride mixed with elderly confusion would mean she’d soon be telling everybody including the check-out chicks at Coles: “Oh, this is my JENNY! You know that lovely Bill Bailey chap off the TV? Well, he’s decided to had over the reigns and give his entire career to HER!”

The next day I met the gang at Australia Zoo and then drove Bill back to Brisvegas, during which we chatted tons about comedy, how he writes his shows, where things are at comedically for me and what the best plan of attack might be from here. He then gave me some really cool advice (which too, is making my head spin) on taking the next step, again, offering to help point me in the right direction and help where he can. We’ll see what evolves in the next couple of months, but at this point I’m pretty sure the UK is in my not-too-distant future….

There’s not even an expression in language (not just English, but any language, full stop) to encompass how I feel about all this jazz.

So for now, this will have to do:


See? I told you. I should win an award for outstanding achievement in incredible displays of uncoolness.

But thank you for listening. xx

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