At times, the barrister and producer of popular ABC television series Rake, stopped to punctuate the air with his index finger for added effect, reflecting on occasions when he felt a judicial officer may have held his long hair against him.

Among tips on how to distract a jury while a counsel is speaking and the merits of being a “good actor”, his one prevailing pearl of wisdom was that “judges are mad”.

“What they didn’t teach you in law school was, indeed, that judges are mad; nearly all of them, by definition: ‘mad as a judge’. It’s as true as ‘drunk as a judge’, which was originally ‘mad as a judge’,” Mr Waterstreet said.

Reading from a yellow notepad, which he confessed to scrawling his speech on while in court the previous day, he paused at a number of junctures along the way to exclaim “judges are mad!”.

Mr Waterstreet illustrated his point with a number of high-profile cases he has been involved in, when either a judge clashed with counsel or acted in a manner that he simply put as “mad”.

The sentencing of artist Nigel Milsom for armed robbery was one focus of the talk. Mr Waterstreet represented Mr Milsom in his criminal case, which was sent back to the District Court for resentencing in 2013. The NSW Court of Appeal had found evidence of apprehended bias on the part of the sentencing judge in Mr Milsom’s case.

“Take it from me, the Court of Appeal castigated the judge and in no way approved what he did. And we went back and … [Mr Milsom] didn’t serve another day in court,” Mr Waterstreet said.  

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While waiting on the outcome of his appeal, Nigel Milsom won the $150,000 Doug Moran National Portrait Prize on remand. He later went on to paint a striking black and white portrait of Mr Waterstreet in 2015 that beat all other entries for that year’s Archibald Prize.

Mr Waterstreet quipped: “Lo and behold, that putrid painting of me won the prize”.

Earlier in the proceedings, when Mr Milsom was unexpectedly refused bail, he was cowering in the fetal position and “crippled with depression and anxiety”, Mr Waterstreet said.

“It’s a very sorry sight to be in a court in NSW where the defendant is curled up in a ball and cowering and in shock [but then] suddenly the judge is galloping the other way.

“One of the reasons why I’d say to you ‘judges are mad’ [is] because that man went through hell because of the to-ing and fro-ing, the pendulum effect, of someone who is ‘plus and minus’, good and bad, and a human. But whether judges should be judges is a matter for the Attorney-General,” Mr Waterstreet said.

“I couldn’t be a judge because I have no judgment and that’s a very good reason why I’m barely allowed to practise,” he said.

The barrister’s insights are being sold in a series of “100 non-TED talks”, with tickets for $27 a pop.