Charlie Pickering 'Desperately Needs To Make Strangers Laugh In A Room'

When we call Charlie Pickering to ask him about what makes him laugh, it’s a weekday morning and he’s on dad duty, ahead of his return to television with his news comedy show The Weekly. 

He uhms and ahhs when asked what makes him laugh – you can almost hear his brain ticking over, trying to find the words to describe what he finds funny. Through the ‘hmms’ and long pauses, he says, “It's actually challenging to articulate, isn't it?” 

Pickering knows his next sentence is going to sound sanctimonious, but he says it anyway, but not before noting that he knows it’s “gonna sound terrible”. “I was gonna say 'the truth', but that's not really — that makes me sound like an evangelical comedian.”

This is what he actually means: “I think what makes me laugh the most is when someone's description of something is absolutely spot-on and true, but it's said in a way that almost goes beyond what you can politely say about something.” 

He brings up smartly dressed Chicago comic John Mulaney, and his 2018 Netflix special Kid Gorgeous – watch it – as an example.  

“Like every comedian in the world has done jokes about Donald Trump, right, and I saw Mulaney's special and it was like, 'Surely there's no fresh takes on Donald Trump.'  And [Mulaney] describes Donald Trump as being like a horse in a hospital, and it's like there's a horse loose in a hospital and he has no idea what he's doing, but you're gonna watch, because it's a horse in a hospital, right? To me it was like the best way to say what we were all seeing but in a way no one's thought of saying it.”  

Both Monty Python and Documentary Now!, a spoof on the documentary genre, from Bill Hader, Fred Armisen, Seth Meyers and Rhys Thomas, makes Pickering laugh in the same way, and for the same reason.  

“It's like parodies of the great documentaries of all time, and I'm like a massive documentary addict, and so these parodies are unbelievably accurate parodies and they are so funny. So Documentary Now! just makes me laugh whenever I watch it.

“It makes me laugh because it gets to the reality of something that no one's talking about, in some way. Like Monty Python, everyone focuses on how surreal they were, but the fact was they were great because they were parodying everyone taking themselves so seriously, and they got under that. 

“I think that's what makes me laugh is when people have the temerity to take themselves seriously when the truth is that everyone in the world – with the exception of a few people – everyone in the world is still children faking it, like pretending they know what they're doing.”  

Pickering’s own comedy, and his sense of what is funny, has changed in some ways as he’s gotten older – although some things are as funny now as they were in childhood.  

He describes fart jokes as the “great leveller”. “Everyone loves fart jokes, that's true. But for me, it's what you do with them [laughs]. For me they have to be a surprise, they can't be too deliberate – I think that's important.”

But what’s changed for Pickering is the question of both who has the opportunity to speak, and who is the butt of the joke. In 2006, his MICF show, Auto, was made up of stories from his time at high school in the late ‘80s and early ‘90s, and he scored a book deal “to write the book of that show”. 

“I started writing and I got about half the book written, and it was great. And then as I started to read over everything I became really aware of the level of just raw privilege in everything I was saying. And so that meant now that book I have to rewrite it with that perspective, and I think that's the thing that has changed [His book Impractical Jokes was released in 2010]. 

“I used to be very cavalier and not really think about, I guess, structural inequality in the world with my comedy – this is a bit serious and you were probably hoping I'd say something like farts made me laugh more when I was young and now it's politics. 

“What's changed is I'm more aware of where jokes can fit into a broader narrative of the world, does that make sense? And so I really don't like jokes that are at the expense of anyone that's further down the food chain, and I really don't laugh as much as I used to at comedy that picks on people.”

Pickering says that he was “raised to believe that a sense of humour was really important”, describing his dad as a practical joker. 

Speaking through a chuckle, Pickering admits that he was obviously drawn to making people laugh as a career because “I'm very needy and I'm clearly trying to make up for some big gap in my childhood that lead to a malformed human being that desperately needs to make strangers laugh in a room”. 

Ultimately though he concludes: “The main reason I do it is it's just great fun, and it is a service. It's a job that makes people feel better. If you can make a room full of people feel better than before you walked into the room, that's a pretty cool thing to do for a job.”  

The Weekly With Charlie Pickering airs Wednesdays on ABC.