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But the years of hard slog up the autobahns and routes nationales finally began to pay off on Wednesday when the 28-year-old earned himself a healthy paycheck by knocking former champion Lleyton Hewitt out of Wimbledon.
The world number 189 could be forgiven for shedding a few tears after the landmark win of his career, thinking back to the years between 2004 and 2009 when he was quite literally living life on the road.
"I cried like a little girl. Just happy and emotional and everything," he said after beating Australia's 2002 Wimbledon winner Hewitt 6-4, 6-4, 6-7 (3/7), 6-2.
"I still have the van. It's parked in Germany at my parents' place. After the match, I just sat down and it took its way. I couldn't really control it," he said of the tears.
Brown, whose frustration with the Jamaican authorities finally gave out when he switched nationality to his mother's native Germany in 2010, is one of the most recognisable players off the court with his long dreadlocks, vests and chilled out manner.
But now he is making waves on the tennis court, reaching a Grand Slam third round for the first time.
The victory took his Wimbledon earnings up to £63 000, which already more than doubles his winnings to date this year, by some margin.
"It's a pretty big paycheck up to now. And the tournament's not done yet," he said.
His earnings could rise to £105 000 if he beats France's world number 111 Adrian Mannarino and makes it to the last 16.
So there is little chance of him revving up the van again any time soon.
"I haven't been doing that since 2009. It just doesn't work, playing the challengers and tour events. Just going from tournament to tournament, you can't do it. It's too far around," he said.
He played down talk that he is the coolest man on the tour but said he had no plans to change his style.
"Difficult to say anything about that. I've looked like this for 28 years, so I'm pretty much used to it," he said.
"Besides that, of course, for other people sometimes it's different. This is the third time in the main draw here. So I'm sure a couple people have seen me play already. The players are used to playing against me or practicing with me.
"Everyone that didn't know me before, they have to get used to it. I'm not going to change."
Brown won fans on the 4 000-seater Court 2 with his serve-volley style and casual racquet toss on downing Hewitt.
His shot to win the first set was old-school tennis magic.
Brown threw himself at full stretch to volley a Hewitt drop shot, just managed to get his racquet on the ball, which landed on the net and dropped over the other side.
Brown has 17 000 followers on his Twitter account (@dreddytennis), and he was wearing a special "Dreddy" t-shirt with a stylised picture of himself on the front, created by the designer wife of one of his friends.
But while other tennis stars dabble with fashion sidelines, he is not about to make a fortune selling them.
"I only have three, so no," he said.
