From the now-infamous Maclean's interview, where he admitted to having a 16-year-old boyfriend and consequentially was removed from the magazine's 1996 honour roll, to his not-exactly-subtle transformation from a clean-cut Cape Breton kid to a punky, flannel-clad fiddling bad boy, MacIsaac has certainly raised a few eyebrows in his time.
But for the past two years, the 24-year-old has kept a fairly low profile, performing only once every so often. The last time he played Calgary was as part of last year's folk festival.
So, what has MacIsaac been up to during his absence? His answer is shockingly blunt.
"The year before, I was just sort or vacationing, hanging out, smoking cocaine, doing a whole lot of weird things and not getting much done," says the award-winning musician nonchalantly.
"It's only been since this January or February that I've been working really hard again."
On Nov. 9, MacIsaac will release Helter's Celtic, his first proper full-length CD since 1995's Hi, How Are You Today?
It's a personal victory for MacIsaac, who felt pressured by the expectations of his record label to produce another hit record and began smoking drugs to relieve the stress.
"It was out of boredom and wanting to find some way to escape the project that was on my head at all times, which was to make a new record. I reverted to getting as high as I possibly could. I got as high as I wanted to with that drug. I didn't go to heroin or anything like that," he says.
"(Crack) is more of a mental addiction than anything else, and mentally it overtook me and I got really deranged on it at one point. But I had enough brains to get away from it."
Feeling guilty about how he was treating the people closest to him, and their tough love approach towards him, it finally became clear to MacIsaac that he had to break his habit.
"That was the only program, realizing that I had been a (jerk), and that I was creating bad vibes for other people.
"The experiences over the past couple of years have been pretty intense for some of my friends and I still genuinely try and apologize daily."
While he has almost successfully shut out the drug that overtook his life for three years, MacIsaac -- who just moved out of his Toronto pad and is debating about whether or not to sell his Nova Scotia home -- admits he has not yet found anything that fills the void that cocaine left.
"I'm still staying in a hotel beside where all the crack dealers in Toronto are, and I'm still getting an urge to stop (to buy drugs) nightly," he says.
He believes because of his celebrity that talking about his problem may help others with similar addictions.
"I've been on the Carnegie Hall stage and I've also been without shoes on Dundas St. in Toronto trying to buy a rock," he says pensively. "I've seen both ends of the spectrum. You gotta help whenever you can, no matter who needs it, and that includes talking about experiences."
This year was also a tough one financially for the performer, who was introduced to a national audience when he toured with The Chieftains at the age of 16. As a result of his habit and his new music not being released by a major label, MacIsaac says he nearly went bankrupt in July.
"I was getting to a point where I was working on one particular project and nothing was getting out that was considered worthwhile to be putting out," he explains.
"I was getting a bit concerned about where I was, which led me down a path where I became a crackhead."
He says his new label, Loggerhead Records, has been "overly supportive and have dealt with a complete madman whose come from very bizarre situations to put out a record. They've been very caring to this point."