In 1997 Charlie Pickering made his debut appearance at the Melbourne Comedy Festival. It had already been a long road for the man who would later become one of Australia’s best-known comedic presenters, but that wasn’t where his working life began.

“My very first job was stacking shelves at the local supermarket,” says Pickering, who grew up in Melbourne’s Brighton East. “It was all very traditional. I did it for pocket money, but also to have a job. As parents go, mine were pretty generous. But they also tried to instil in me a good attitude towards work and working hard. Getting a job in a supermarket was a good place to start.”

Pickering, who went to the prestigious Brighton Grammar School, was never going to stop at a supermarket job. The surprise for his parents was, he was never going to settle for a standard career, either.

“I knew when I was 12 I wanted to be a comedian,” he says. “But you can’t tell your parents you want to be a comedian when you’re 12. You have to say something serious.”

A big fan of UK comedy legends Monty Python; Peter Cook and Dudley Moore; ex-pat Clive James; and local comedy team The D-Generation, Pickering discovered they all studied law before shifting into a comedy career. Knowing law school was much easier to sell to his parents than professional laugh-getter, Pickering sensed a circuitous route to his dream job.

“I knew my parents wanted me to become a lawyer,” he says. “I reckoned if I studied hard, I could get into law school and then start doing comedy. So I worked hard in Year 12 and got in. I auditioned for the law review in my first week there, and from that point on I dedicated myself to comedy.”

Pickering graduated from Monash with a degree in Arts/Law. He also worked on five law reviews while there. “I ended up producing and directing and writing the shows and being in them,” he says. “I was doing everything I could.”

That hard work paid off. Pickering quickly became a mainstay of the Melbourne comedy scene, his live work leading to television appearances – first on pay TV, and then in 2009 with the one-two punch of becoming a team captain on the Shaun Micallef-hosted gameshow Talkin’ ‘Bout Your Generation and a panellist on the then 7pm Project. He would go onto host that show, and in 2015 he became the man behind the desk of the ABC’s news satire show, The Weekly.

Comedy may have been where he’s made his mark, but the skills he developed through law have helped shape his approach to comedy. “Just on a daily basis, comedy is a process of thinking,” Pickering says. “Law is a thought process similar to journalism or medicine or engineering – it’s a way you go about solving problems. That comes in handy when you’re writing comedy. In law you take a situation and you’re trained to look at it from as many different angles as possible. To reason your way to certain outcomes. Those skills cross over into comedy pretty well.”

Working as he does in an area of comedy that comments on politics and news, Pickering has also found his law training helps him identify a subject’s weak spots.

“There’s an architecture behind power,” says Pickering. “A lot of the time in comedy, you want to be speaking truth to power. You want to take on the biggest, strongest people, and sometimes ridicule them. Understanding the legal architecture that holds them there is useful.”

The main thing that’s stayed a constant with Pickering throughout his working life is the simple desire to make people laugh. It’s been with him right from the time his grandmother gave him a recording of Scottish comedian Billy Connolly when he was 12.

“I heard that as a kid and I just thought, that would be the best job,” says Pickering. “Around that time I was getting into a lot of trouble for mucking around in class. I had a teacher say to me, ‘Look, that’s really funny, but you have to settle down’. I turned around and said, ‘Really? You think I’m funny?’”

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