In 1996, MacIsaac toured the United States as an opening act for the Chieftains. It was widely reported in the media that another opener, folk singer Nanci Griffith, dropped out of the tour because she objected to MacIsaac's musical style, but Griffith later confirmed in "Rolling Stone" that her primary conflict was not with MacIsaac's style, but with tour organizers over how much time was available for her after the addition of MacIsaac to the bill. On a 1997 "Late Night with Conan O'Brien" appearance, his leg kick lifted his kilt high enough that his genitals were visible to the studio audience, although they were blurred out in post-production before the actual broadcast. In 1998 MacIsaac fought successfully to be independent of his record label. He subsequently signed with the independent label Loggerhead Records for his 1999 album "Helter's Celtic". During the promotional tour for that album, he indicated to the press that he had battled an addiction to crack cocaine from 1997 to 1999. In 1999, a journalist for "The New Yorker" noted MacIsaac's rock-star bravado and eccentricities. In December 1999, MacIsaac screamed obscenities at a New Year's Eve rave in Halifax; the performance led to cancellations of his concerts across Canada and a "media frenzy over his perceived downward spiral". MacIsaac got into a media spat with his label Loggerhead after the label sent out a press release distancing itself from his actions. Also the same year, MacIsaac told the "Halifax Chronicle-Herald" that he was on the verge of declaring bankruptcy, retracted the statement within a few days, and then actually filed for bankruptcy several months later. In 2003, MacIsaac was alleged to have made a racist statement on stage, at a show where he reportedly accused an Asian woman in the audience of spreading SARS. He subsequently stated that the comment was intended as an ironic parody of racism, and sued the "Ottawa Citizen" for misrepresenting the statement as racist when in fact he was speaking out against racial profiling happening in Canada at the time. In 2005, MacIsaac signed on with Linus Entertainment, forming a rock band with himself on lead vocals and guitar. In 2010, MacIsaac wrote a charity single, "Dreams", to benefit Kwame Nkrumah-Acheampong, a skier from Ghana who was the first Ghanaian athlete ever to compete in the Winter Olympics. In addition to Matthew Harder of the band House of Doc and Geoffrey Kelly, Vince Ditrich and Tobin Frank of the band Spirit of the West, Nkrumah-Acheampong himself participated in the recording, playing traditional Ghanaian percussion.