During his early career, MacIsaac subtly acknowledged his sexual identity, sometimes wearing a set of rainbow flag freedom rings on a neck chain in promotional photos, but avoided explicitly coming out to the press. Hi™ How Are You Today? was a double-platinum selling Canadian record and earned MacIsaac a 1996 Juno in the category Best Roots & Traditional Album – Solo.
The song peaked at number 13 on the Canadian RPM Top Singles chart and found minor success in the United States, reaching number two on the Billboard Bubbling Under Hot 100. MacIsaac's album Hi™ How Are You Today?, featuring the hit single 'Sleepy Maggie', with vocals in Scottish Gaelic by Mary Jane Lamond was released in 1995. According to MacIsaac, spoken during his February 25, 2017, concert at Koerner Hall in Toronto, they are now divorced. The two met and MacIsaac opened for the White Stripes concert in Glace Bay in 2007. He is also a distant cousin of the White Stripes guitarist and lead vocalist Jack White. His cousins Alexis MacIsaac, Wendy MacIsaac and Natalie MacMaster are also touring fiddlers. She also appears on his album Helter's Celtic, which was recorded at Metalworks Studios in Mississauga, Ontario. His sister Lisa is also a fiddler, who has her own alternative country band, Madison Violet. MacIsaac was born in Creignish, Inverness County, Nova Scotia.
