Playing old-time folk tunes and Americana
at a ragtime pace, rounded by jazzy vocals
and a gritty finish, Captain Cowboy and
the Money Maker animate the stories of
forgotten songs in a way that sparks a smile
and inspires applause.
INSPADES met with the busking duo at
Jimmy’s Coffee in Kensington Market, an
eclectic patch of diversified culture in the heart
of Toronto where the pair often performs.
“When we first met, we bonded over
this love of old country music,” recounted
Money Maker, mentioning Hank Williams
as one of their pseudo-mentors. The duo
met at an open mic night in the small town
where they lived, and it wasn’t long before
the two were reveling over their passion for
music and history.
“We found this sweet spot in the 1900s and
the 1930s that we absolutely love,” said Money
Maker, describing their musical exploration
as they experimented with song covers; “As
opposed to wanting to learn the songs, we
wanted to learn the stories.”
The couple began their journey as
professional musicians when they auditioned
for the Subway Musicians Program run by the
Toronto Transit Commission (TTC). “I didn’t
think we were going to get the TTC performing
license,” admitted Captain Cowboy, as the two
had never performed together and had no
act under their belt. “When we got it,” Captain
Cowboy continued, “we said, ‘Let’s not give
ourselves another option or get ourselves other
jobs. Let’s just do this, and if we fail, we fail.’”
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Prior to the TTC audition, Captain Cowboy
and Money Maker were miserable with their
boxed-in life and “square” jobs; Captain
Cowboy worked fifty-plus hours a week as a
contractor, while Money Maker juggled two
waitressing gigs. “We lived in this tiny town
that was basically just an intersection with the
gas station,” said Money Maker, “We weren’t
saving any money and we didn’t have any
time to see each other. It was so horrible.”
When they acquired their TTC license, the
pair gleefully broke up with their mundane
lives and hightailed it to Toronto, with
adventure before them and serendipity on the
horizon. “We thrust ourselves towards it with
reckless abandon and let our act evolve into
what it is now,” said Money Maker.
While Captain Cowboy and Money Maker
were ready to embark on a fresh chapter in their
lives, arriving in Toronto in November made for
a “rocky start”. It was too cold to busk outside,
daylight sank by late afternoon, and the couple
had yet to establish a strategy for busking.
Before the move, the pair managed to
accumulate a small cash stash, allowing them
to pay three months rent up front once they
found a small attic apartment on the Danforth,
freeing them to focus on honing an act instead
of stressing over finances.
“We were putting rice in our eggs to
prolong our breakfast and keep our bellies
full for longer, but it was so worth it because
it was empowering to be so free,” recalled
Money Maker of those first tough months in
the big city.