top of page
  • Writer's pictureBillie Proffitt

Oh! For the Love of Charlie... When Law Marries Art, For Better or For Worse

I’m frantically struggling to type a two-handed text out whilst balancing my clutch under one arm, and trying not to break too much of a sweat in the sweltering humidity all at the same time, as I heel-toe stride across the top side of Sydney’s iconic Archibald Fountain, hoping I’m not too late. If there is one thing I have learned about Barrister Charles Waterstreet, it is that he keeps a schedule of his own and to no one else’s. It isn’t rude, it simply is. With his biopic hit show still running, Charlie, as I’ve come to adore calling him, is not your average lawyer. His bizarre schedule does not arise out of arrogance, as perhaps most people would pigeonhole such powerful men’s main personality traits into, but out of the sheer truth that he marches to the beat of his own drum. But what has become of Rake, sixteen years after becoming sober?

“I’m not going to be a lawyer when I grow up,” he tells me and goes back to his uncorrupted Diet Coke. The man sitting with me is wildly attractive, most notably for his age. Accepting the honor of Nigel Milsom’s winning subject in the 2015 Archibald Prize on his sixty-fifth birthday, he never has an empty bed unless he chooses to, and I have yet to meet one of them over thirty. He is a photographer, model, painter, writer – with both a Sydney Morning Herald weekly article and a handful of (absolutely Australian and hysterical) books, a successful screenwriter and producer... His friends are some of the most notable contemporary artists of our time, not to mention his list of clients. Many describe him as all over the shop, as he tends to have know-how and some one he knows in every facet of life, but I am finding that this suave version of the Absent-Minded Professor is indeed his charm, and by no means a realistic indication of his attention to detail, nor his ability to get to the heart of the matter in any conversation or debate. When I asked how he came to make art the center of his universe, despite his lucrative and successful career in law, he explained that he has always found his comfort crowd to intrinsically be creatives: actors, musicians, writers and painters, and increasingly so as he gets older. His threshold for close-mindedness has grown small and in the space that was opened up by eliminating it, his own creativity – and therefore his fulfillment – has flourished.

Waterstreet was raised in Albury, on the New South Wales side of the Murray River, the first child of five. His parents owned one of the local pubs and lived above it, where the only artwork he experienced was one Indonesian painting of a woman all in shades of green, which hung on a wall mostly obscured by the cigarette smoke haze. He calls his father, “a bastion of art amongst philistines,” for his consistent storytelling abilities behind the bar. Keeping any drunks’ attention is quite a feat, but to entertain them enough to control them is a higher level of talent. Waterstreet Senior seemed to possess it, holding court and happily dancing amongst the craziness of publican life: government interference via liquor laws, running a boarding house, accidentally having five children, Charlie’s list goes on... He believes this constant influx of “nutcases” is where his interest in the social margins began, eventually inspiring him in all kinds of artistic facets, and his father’s stories introduced him to his boundless love of words.

His mother, “an unbelievably hopeless alcoholic,” was in and out of Kenmore, the notorious mental health institution in Goulburn, for her reliance and complications due to her main liquid habit. He remembers going to visit her but mainly recalls the annoyance when numerous other inmates would recognize his father and stop them for a chat, making the day much longer than anticipated. There is an anecdote in his first book, of passing her on the stairs of their home one morning as he was leaving for school, her hands and arms bloodied from breaking the windows of their own family establishment to fetch herself two bottles of brandy, which she coddled in her blood-stained nightgown. They never made eye contact, nor acknowledged the event, for the rest of her life.

Waterstreet was not shielded from these painful truths, as he also told me of when he was seven years old playing in the schoolyard, when a little boy came up and said to him, “My Mum says your Dad’s a playboy.” Was he really? Or was this just a small-town viewpoint of a larger-than-life man? We all know the term “tall poppy” in this country, and with Waterstreet Senior’s physique, which is told to have been even greater than that of his son’s, and grandson’s is today, then he personified it, in body and in spirit.

It’s common knowledge that Waterstreet’s antics have landed him in trouble many times throughout his life. Be it bad choices in women, addictions, his bleeding heart for the creative underdog, or his shrewd sense of business that have left him broke, hurt, smashed on the rocks of life, and living as a confused bachelor, it is never without a beautifully emulated story that usually ends with me holding my stomach, and rubbing my cheeks, in painful laughter. Ahem. Regardless of the extent your heart wrenches for the characters in the tale, his irreverent yet humorous storytelling always finds a way to captivate his audience without pity. He is so engaging that you often forget: he is the character in his own punch line. For instance when a wry smile crept across his face as he recounted for me a story from his only wedding.

Dressed in full formal coattail attire he stood to give a speech to the 300-some-odd, most well-to-do guests of Sydney’s elite, which opened with the adorable story how he met, and of course, fell in love with Fiona. But a few moments into it his ex-girlfriend, actress Kate Fitzpatrick – “Who dawned all black for the occasion, never a good sign,” he noted on the side as I scribbled in my notebook – stood and shouted, “That is when he was with meeeeeee!” before dramatically storming out of the reception. The next day she sued him for palimony, eventually losing… “But it was one hell of a way to start a honeymoon,” he says.

These outlandish and sparkly visions of past awkward moments and judgments that some might consider “mistakes” in the course of his life, provide hope for me in my own… That taking chances on the “just maybe” opportunities that arise in one’s life – be it with a potential love, a chance at a different occupation, a random quest or achievement that most people believe is out of your reach, or whatever else – may not work out the way you had originally planned, but the experience still remains in favor for your greatest good. Yes, a lot of times after these forks in the road you are left embarrassed as the journey comes to a close, however short that jaunt was… Maybe you’re also bloody, bruised, broken, exhausted, poor, crying, lonely, depressed, robbed, or maybe you’re stuck naked at a public swimming pool, post-first date on your eighth day living in Hong Kong. Having found yourself on a train home wearing an overpriced towel you were forced to purchase from the aforementioned pool, we would consider this situation not ideal. Maybe! But it’s a bloody good story to make your friends laugh, or cry, or inspire, right along with you, or maybe even at you… But really, who cares amongst friends? And if you’re comfortable enough in your own character, what do you care of how anyone else views you?

Waterstreet is a man who lives his life by hefty example in this way: he is not afraid of failure in following his bliss. In a world that could so easily turn to beige, he believes in the glimmer that every new opportunity at happiness may just be the one dream come true that makes the other pains worthwhile. His approach to life sparks the Edison quote in my head on a new level of understanding: “I have not failed. I’ve just found 10,000 ways that won’t work.”

Most of this interview was done on a Saturday night in Sydney’s fantastically technicolored Newtown. That probably doesn’t surprise anyone, but the fact that it was also as we chose sex toys and lingerie at his favorite adult shop, Max Black, added some new angles to the conversation. Actually, come to think of it, that element probably doesn’t seem out of character either. Walking out onto the street carrying one of their infamous black and white striped bags made me feel both empowered and embarrassed at the same time. Yet shortly afterward, I realized “popular” should join the list too...

I couldn’t tell who was getting more attention: my self as the blonde sans bra swinging the dirty toys bag in unison with her stride, or Charlie, as the debonair older gentleman escorting her down King Street. I fear when I purchase the new Mickey Avalon album I’ll find myself as a cameo in a raunchy verse of a song, a tag-a-long to the infamous Australian inspiration that is Charles Waterstreet.

I had heard tales of Waterstreet from a number of acquaintances before I ever met him for myself, most of them focused on his thought-provoking, yet quietly hysterical one-liners. He is a legendary character around Sydney, in particular in the art scene. While on a tour of the esteemed Archibald prize a few years ago, at The Art Gallery of New South Wales, the speaker noticed Waterstreet pass by toward the portrait of himself, again with an impeccably attractive young woman throwing her head back in laughter while hanging on his arm and I imagine his words… Across the room, Jasper Knight called out hello and inquired what Waterstreet thought of his notorious “loose cannon” (and now late client) Adam Cullen, since Cullen was the artist who had painted him that year. To which Waterstreet replied – for the seventy-some people who now stood as his audience – “Every lawyer needs an Adam Cullen! It’s good for business.”

His adoration and love of women, sex, and the naked body are no secret. He flirts mercilessly with the Venuses of this world, is often thanked in the forwards of naughty books, or in fact giving the opening speech at erotic book launches, and even other times, gracing its pages with either his skin, (all of it), or his words... Which of those is more risqué, I couldn’t choose.

One early morning, a friend of mine was driving down William Street as he crossed Waterstreet walking toward the City. Offering a lift, they discussed life and beautiful women on the ride, passing one such lady my friend asked if she was one of his countless, appealing female law associates. “Oh no, she isn’t mine. Could be, but isn’t.” After a brief pause, he added, “Sebastian, I’ve always considered beautiful associates as God’s way of giving back.”

When I told him this story about himself, I inquired if sex has become his replacement addiction for conscious-altering substances, and he agreed, following his admission with, “Darling, I suggest you choose obsessions that won’t kill you.”

Regardless of his clear admiration and affinity for aesthetic beauty, Waterstreet is also one of the deepest conversationalists and thinkers that I am lucky enough to share meals with. He questions everything about life, gravitating toward the idiosyncratic, yet somehow finding the extraordinary in the ordinary. And isn’t that the basis of all art? He told me, “There is so much magic hidden in plain view, but you have to alter the perspective of your universe to see it.” Even the words he chose in that statement put so much self-governed authority on to each of us, with the notion that we all have a universe of our own – that we are in fact, our very own God.

It is as Francois-Marie so eloquently and heavy-handedly stated, that: “With great power, comes great responsibility,” – which is true not only in government, but for each of our own lives as well: be the subject our happiness, stability, success, freedom, desires, or anything else. And as Waterstreet’s Aunt Faith used to say, “A good cliché hits a nail on the head.”

It appears to the rest of us that Waterstreet has spent the first half of his life trying to kill himself, and now the second half trying to live forever. “You learn to love your armor more than what you’re protecting. You either embrace it or have to spend your life healing your inner child.”

A controversial approach to what many would consider a healthy lifestyle, but nonetheless, it is no doubt his very own.

24 views0 comments


Rated 0 out of 5 stars.
No ratings yet

Add a rating
bottom of page