It took three years, however, before Dempsey put issued his first solo album. They Don't Teach This Shit in School, released in March of 2000, was a commendable but self-conscious effort that featured a smoother, less visceral recording of "Dublin Town." Despite its relative lack of commercial success, They Don't Teach This Shit in School earned Dempsey a number of admirers within the industry. Sinéad O'Connor
agreed to collaborate with Dempsey for the title track of the Negative Vibes EP in October 2002, prompting the renowned singer to include him as the opening act on her subsequent European tour. Released in May of 2003, Seize the Day was produced by former O'Connor
collaborator John Reynolds, and featured a guest guitar spot by the legendary Brian Eno
, but the album's most striking feature was the performance of its central figure: Dempsey had matured immeasurably as a songwriter and as an individual, better able to articulate his strong sense of morality and no longer apprehensive to sing in his natural, earthy tone. The album was released in the U.K. in May 2004 on the expatriate label IRL, and earned the artist two Meteor Ireland Music Awards.
Arriving in 2005, Shots became Dempsey's first album to be simultaneously released in Ireland and the U.K. Shots debuted at the top of the Irish Albums chart and achieved platinum status before the year was up, and Dempsey was accordingly honored as Best Irish Male at 2006's Meteor Awards. In fact, 2006 proved to be a banner year for Dempsey: the New York-based label United for Opportunity began releasing each of Dempsey's albums in America, Sing All Our Cares Away (a compilation of tracks from Seize the Day and Shots) became Dempsey's first release in Germany, and the singer's first live album, Live at the Olympia, arrived in June. All of this activity resulted in Dempsey winning the Best Irish Male award in 2007, marking his second consecutive win at the awards ceremony. 2007 also saw the release of Dempsey's fourth studio album, To Hell or Barbados, which debuted at number one in the Irish album charts. An all-covers album entitled Rocky Road followed in 2008. ~ Dave Donnelly, Rovi