Gary LeDrew: Artist, Bootlegger,
Sailor, Santa Claus, and the Most Interesting Man in Canadian Art History
From Toronto's underground nightlife to the
lighthouses of Cape Breton, the remarkable life of a true Canadian original
There are artists, and then there are characters.
Gary LeDrew is emphatically both.
In a career spanning six decades and at least as
many identities — painter, underground nightclub operator, sailing bosun,
computer executive, professional Santa Claus, and Cape Breton cultural icon —
LeDrew has lived the kind of life that most novelists would reject as too
far-fetched. His story is a vivid, whisky-soaked, salt-sprayed portrait of
mid-century Canadian bohemia, threading together the unlikely worlds of
Toronto's art underground, the global rock-and-roll touring circuit, the dawn
of digital art, and the rugged maritime landscapes of Nova Scotia's Atlantic
shore.
This is that story.
Gary LeDrew spent his early childhood living at the Louisbourg
Lighthouse in Nova Scotia before his family relocated to Uxbridge, Ontario,
traveling by way of McMasterville, Quebec. He attended local public schools but
chose to leave high school at age 17 to enlist in the Royal Canadian Navy,
serving a three-year term. Following his military service, LeDrew cycled
through a diverse series of working-class jobs. He trained as an apprentice
silk screen printer, worked as a shepherd, and gained employment as both a
steelworker and a specialized stainless steel welder. In 1965, he walked away
from these traditional trades completely, moving to Toronto to fully embrace a
bohemian lifestyle and pursue a career as an artist.
Key Biographical Milestones
- Childhood Home:
Louisbourg Lighthouse, NS
- Relocation Route:
Moved to Uxbridge, ON, via McMasterville, PQ
- Education:
Public school; left high school at age 17
- Military Service:
Royal Canadian Navy for 3 years
- Early Trades: Silk
screen printer apprentice and shepherd
- Industrial Work:
Steelworker and stainless steel welder
- Turning Point: Quit
all industrial work in 1965
- Destined Path:
Moved to Toronto for an artistic, bohemian life
Part One: Young Man in the City
— Toronto in the 1960s
By the late 1960s, Toronto was quietly convulsing.
The city that had long been defined by its Protestant rigidity — "Toronto
the Good," as critics mockingly called it — was beginning to crack open
under the pressure of a generation that had no patience for last calls, early
closings, and provincial respectability.
Into this city came Gary LeDrew.
A Canadian artist by instinct and a storyteller by
nature, LeDrew embedded himself deeply in Toronto's art scene during a period
of genuine cultural ferment. He worked as an independent, eccentric designer
and self-described "bonded artist" — a figure who carried his
portfolio into bars, communal spaces, and whatever rooms he could find that
smelled like turpentine and ambition. He moved in the same bohemian orbit as
legendary Canadian painters like Graham Coughtry, Robert Markle, and Harold Town
— figures who defined Toronto's abstract expressionist moment and whose
influence soaked into the walls of every serious studio in the city.
LeDrew's own oil paintings from this era reflected
that environment directly. He focused heavily on the human figure, rendered
with the raw, high-energy abstraction that the Toronto scene celebrated. These
weren't gentle canvases. They were alive with the particular electricity of a
city that was finally starting to believe in itself. He staged two major
exhibitions in Toronto during the decade — serious showings that announced him
as a credible voice in a crowded and competitive scene.
In 1969, he was living in a communal house on
Hazelton Avenue, having moved into the room recently vacated by a young
folksinger named Murray McLauchlan. The two developed a lifelong friendship —
one of many that LeDrew forged during those years of shared kitchens and
late-night conversation that would define the shape of English-Canadian culture
for a generation.
Part Two: Uxbridge and the
Straight Life — 1970–1974
By 1970, LeDrew had married and moved to Uxbridge,
a small town roughly eighty kilometres northeast of Toronto. He and his wife
Andrea taught at a Free School run by Browndale, a residential treatment
program for emotionally disturbed children. LeDrew taught art and crafts —
channelling his energy into one of the most demanding teaching environments
imaginable.
The Uxbridge years were, by any measure, his most
conventionally respectable. He became Vice-President of the Royal Canadian
Legion and served as chairman of the 1972 Centennial Committee. Perhaps most
improbably, he organized and hosted what is widely regarded as the first legal
beer garden in the province of Ontario — an event that drew the Governor
General of Canada as a guest and raised half a million dollars in a single day.
The man who would later spend five years running an illegal drinking establishment
now had a Government House endorsement on his résumé.
It didn't last. His marriage broke down. He quit
his job and moved back to the city.
Part Three: The Open Water —
Sailing the Caribbean and Beyond
The years that followed were characterized by a
restless, nomadic energy that took him far from the downtown Toronto blocks he
had haunted.
He took to the sea. He sailed
across the Caribbean, delivering racing yachts and crewing wherever he could
find passage. He eventually signed on as bosun aboard The Pilgrim — a historic, full-rigged square-sail
brig operating as a working tall ship — hauling lines and navigating open water
on a vessel that demanded total physical commitment.
He joined a group of friends and
spent a winter in the Bahamas aboard Isla, a 46-foot
trimaran. In the spring, he helped deliver another large trimaran — the
56-foot Tao — back to Toronto. The return voyage took two
months.
Part Four: The Booze Can —
Toronto's Most Famous Illegal Bar
Ontario's liquor laws in the 1970s were, by most
accounts, absurd. Last call came at 1:00 AM, and the regulations governing bars
were so arcane they might have been written by a Victorian temperance society.
For a city that was rapidly becoming a world-class cultural destination — a
regular stop on every major touring circuit — this was an obvious problem.
The solution, for those who knew where to look, was
the booze can.
After-hours clubs, operating entirely outside the
law in the back rooms and upstairs floors of downtown buildings, became
essential infrastructure for Toronto's creative class. Artists, musicians,
journalists, Actors, and miscreants of every description flooded these
underground establishments when the legitimate bars closed. And for five years
in the mid-to-late 1970s, the most famous of these establishments was Gary
LeDrew's.
Located on Queen Street West,
directly across from the historic Horseshoe Tavern, Gary's Bar became a genuine institution on the
global rock-and-roll touring circuit. LeDrew ran it with the particular energy
of a man who genuinely loved interesting company and had zero interest in
sleeping.
The clientele was extraordinary.
He welcomed Mick Jagger and the Rolling Stones on a night that began with a
phone call from writer and impresario Tom Hedley: "Hey — Mick Jagger wants to talk to you. CBC icon
Peter Gzowski was a regular. New Brunswick Premier Richard Hatfield found his
way through the door. Night after night, the underground room on Queen West
hosted people whose fame existed in an entirely different world from the
illegal late-night bar they were sitting in — and that contrast was precisely
the point.
LeDrew wore the label proudly. He openly and
cheerfully described himself as "Toronto's leading bootlegger," fully
aware of the absurdity and the honour embedded in equal measure. He wasn't
mainstream famous. But within the global touring circuit, among the musicians
and writers and actors who needed somewhere to be at 3:00 AM in Toronto, his
establishment was completely, undeniably infamous.
It lasted five years. It left a permanent mark on
his personality.
"The booze can years," he reflected later, "were completely wild. But they taught me everything I know
about people."
At the same
time he hosted the Hospitality suite at Toronto’s Movie Festivals.
Part Five: Film, Computers, and
the Long Road Back
After the booze can closed,
LeDrew moved into Toronto's burgeoning film industry. As the city became a
major North American production destination in the late 1970s and 1980s, his
illustrative skills and instinctive understanding of spatial storytelling made
him a natural contributor. He worked as assistant producer on Double Negative and took on independent creative
contracts across trade shows, film productions, and entertainment ventures. He
spent three months as Richard Burton’s drinking buddy. Befriended Leonard
Cohen, Elizabeth Ashley Howard duff and many more. He wrote a few scripts and Filmmaker
Sydney Newman secured him a grant from the Canadian Film Board to produce his
own feature, Runyon's Law — a project that
was ultimately shelved when changes to Canadian tax law pulled the financial
ground out from under it.
Then things turned bad. He found himself back in
Toronto on welfare, living aboard a friend's sailboat in the sail locker at a
marina. That same friend lent him a Commodore 64 computer. With little else to
occupy him, LeDrew spent the winter teaching himself the machine.
He had meant to use it as a tool for making art.
What he discovered instead was that producing visual work on early home
computers required such deep technical problem-solving — the hardware was
obstinate, the software primitive, the process entirely self-invented — that he
inadvertently became a proficient expert in both hardware and software. It was
the most accidental education of his life, and it proved enormously
consequential.
He eventually pulled himself back to stable ground,
spending three years working as a building superintendent — progressing through
progressively larger properties until he was managing an entire block of
downtown Toronto real estate running from Yonge to Bay Street, north of
Wellesley. He also took on seasonal work as a professional Santa Claus. It was
through one of these appearances that he met the people who ran Wise Guy
Computers.
They hired him. Within a relatively short time, his
self-taught technical expertise had carried him to a corporate executive role —
a position he held for nearly a decade. He later operated his own
computer-related ventures. The man who had spent 1981 on welfare aboard a
sailboat with a borrowed Commodore 64 had, by the early 1990s, built a second
career in an industry that most of his artistic peers hadn't yet heard of.
Part Six: Heritage in Paint —
The Uxbridge Years
After the years of sailing, bootlegging, film work,
and computing, LeDrew found his way back to Uxbridge — and something in him
quieted down long enough to paint seriously again.
The work that emerged was entirely unlike his
Toronto oils. Gone was the abstraction and the human figure. In its place came
a meticulous, nostalgic engagement with historical architecture — the old post
offices, the stone churches, the heritage mills and gabled houses that defined
small-town Ontario's built landscape. Working digitally, he brought to
historical subjects the same total commitment he'd brought to every other
chapter of his life.
The Heritage Series, as this body of work became known,
found institutional buyers quickly. The Toronto-Dominion Bank acquired multiple
pieces for its corporate collection. Reproductions circulated widely. LeDrew
had discovered something that audiences responded to deeply: the quiet
emotional weight of places that were slowly disappearing, rendered with enough
technical precision to feel documentary and enough warmth to feel like memory.
Notable works from this period
include Old Post Office, Gould House, Old Catholic Church, Tin Mill, and Peers Mill Udora — titles that read like a
directory of vanishing Ontario, preserved in careful digital brushwork.
Part Seven: Cape Breton and the
Lighthouse
In 2004, Gary LeDrew did what many Canadians
eventually do, whether by instinct or inevitability: he went home.
He relocated to Louisbourg, Nova Scotia, on the
eastern coast of Cape Breton Island — a return that carried deep personal
meaning. LeDrew had lived as a child on the Louisbourg Lighthouse, one of the
most historically significant and dramatically situated maritime structures on
the Atlantic seaboard. The lighthouse, the sea, and the particular quality of
light on Nova Scotia's coast were not new subjects for him. They were his
original landscape.
The Cape Breton years produced
his most celebrated and widely distributed body of work. Painting from memory,
history, and a lifetime of accumulated visual knowledge, LeDrew created a
Maritime and Lighthouse Series that captured the emotional geography of
Atlantic Canada with rare authority. Major works from this period include Where Canada Begins — Louisbourg 1758, The Light Keeper, Louisbourg Lighthouse 1947, Moxham Castle by Moonlight, and Toilers of the Sea — canvases that are
simultaneously documentarian and deeply personal, the work of someone painting
places he has always known.
He established the Cape Breton Artist — Gary LeDrew
Gallery on Charlotte Street in Sydney, Nova Scotia, and became a fixture in the
regional arts community. His prints have been sold through The Bridge Social,
distributed through Fine Art America, and selected by the Heritage Trust of
Nova Scotia as featured work.
Part Eight: Santa Claus and the
Christmas Book
Because of course there is also this.
In addition to everything else — the bootlegging,
the sailing, the computing, the painting — Gary LeDrew is a professional Santa
Claus.
The casting is not exactly surprising. He has the
storyteller's instinct, the performer's love of a room, and the raconteur's
understanding that a good story told with total commitment can hold any
audience. The same qualities that made Gary's Bar a destination for Mick Jagger
in 1977 translate, with only minor adjustment, into the kind of Santa Claus
that children remember for years.
He went further. Drawing on his
love of Cape Breton's cultural landscape and seasonal traditions, LeDrew wrote
and published the Cape Breton Christmas Book —
adding published author to a résumé that already strained credulity.
"Artist, bootlegger, sailor, film
industry worker, computer executive, and Santa Claus," he summarized at some
point, apparently without irony.
It reads like a joke. It is also completely true.
No comments:
Post a Comment