“We’ve played some of these songs literally
thousands of times,” added Captain Cowboy,
“The only way that it can stay entertaining is
by trying to make her laugh.” Changing the
lyrics, making animal noises and drawing
attention to little mistakes throughout their
performance keeps the pair energetic and
fresh, and actively engages the audience in
the humour of the moment.
“You make your act a smooth-running, welloiled machine, and then you have the fun of
throwing a monkey wrench in that machine
and seeing what comedy comes from that,”
said Captain Cowboy.
Over the past summer, Captain Cowboy and
the Money Maker took their act on the road,
hitchhiking from Toronto to Newfoundland
to busk, play the occasional bar and feed
their zeal for spontaneous living. “There was
plenty of sleeping in parks and on the sides
of highways, but we didn’t want to plan too
much,” said Money Maker.
“Not planning was part of the fun,” added
Captain Cowboy, “it was also part of the
experiment. Could we go to another city,
and reproduce what we’ve managed to do in
Toronto?” Their only plan was to return with
as much money as they’d had at the starting
line, and they were successful.
“We’d show up in a city, drop our case, and
eventually someone would show up and ask
where we were staying,” said Money Maker,
who recounted tales of human kindness and
generosity that left the two feeling “humbled
and inspired.”
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While in Halifax, the house that they were
staying in burned down while they were
busking. With nothing but the clothes on their
back and their instruments, Captain Cowboy
and Money Maker were struck by luck when
Halifolks, an image-based blog capturing the
faces and stories of Halifax, publicized their
misfortune. Shortly thereafter, the story went
viral, attracting coverage from CTV News and
a wave of support from Halifax residents.
“We got backpacks, a tent, sleeping bags,
all this food, a twelve-pack of beer,” Money
Maker laughed fondly at the recollection,
“People who couldn’t donate anything were
still calling us over to have dinner.”
“It was better than everything going right,”
Captain Cowboy agreed.
The Canada’s east coast was kind to the
buskers, who easily found rides along the side
of the highway, which they attributed much to
juggling and “looking like idiots”. While often
drivers are hesitant to pick up hitchhikers,
their quirky appearance seemed to remove all
sense of potential threat.
“How are they going to fit knives into
their pock ets when their pockets are full of
confetti?” Money Maker joked.
While playing on the streets in cities
like Montreal, Quebec City and Halifax,
the standard duet of Captain Cowboy and
the Money Maker would often expand
unexpectedly, as passers-by joined in the
show. “People would come up as we’re
busking and just pull out their instruments,”
Money Maker recalled, “On the Halifax harbour