In 1997 “Dublin Town”, Damien’s first commercial single, reached No. 18 in the Irish charts. HOT PRESS remarked that it was:
“..an underground anthem for disaffected youth and closet balladeer alike”.

A re-recorded version of the song appeared on Damien’s first album; “They Don’t Teach This Shit In School” released in 2000. His next release, the “Negative Vibes EP”, (2002) featured Sinéad O’Connor on the title track and led to an invitation to support Sinéad on her 2002/2003 Irish, UK and European tour. Damien’s second album, “Seize the Day”, was released May 2003 in Ireland on Clear Records via Sony and entered the charts first week of release at No. 5. It has since achieved double-platinum sales. Released in May 2004 in the UK on IRL, the album was awarded “CD of the Week” in the Sunday Times and received enthusiastic reviews in the National and music press. Nominated in four categories in the 2004 Irish Meteor Awards, Damien walked away with two, the only 2004 double winner. A documentary, “It’s All Good: The Damien Dempsey Story” by independent filmmaker Dara McCluskey, that followed Damien’s career progression up to the release of “Seize the Day”, was broadcast on Ireland’s national TV station RTE and shown at film festivals in Ireland and New York. During 2004 Damien toured extensively headlining his own shows as well as supporting Bob Dylan during the Irish leg of his European tour and making his debut appearances at The Fleadh and WoMAD. Damien has earned the passionate support of his peers, one of whom is Morrissey who invited Damien to support him on various UK and Irish dates as well as his autumn 2004 US tour. Morrissey went on to sign Damien to his Attack label, and “Seize the Day” had its U.S. release in October 2004. His third album, “Shots”, simultaneously released in Ireland and the UK in March 2005, entered the Irish album charts at Number 1 and achieved platinum status in December 2005. The album was also released in the U.S. on United for Opportunity Records in June 2006 and Damien undertook a coast-to-coast tour. In February 2006 Damien increased his Meteor Awards by winning in The Best Irish Male category. Recorded in December 2005 at Dublin’s Olympia Theatre and released in June 2006 in both Ireland and the UK, Damien’s first live album, “Live at The Olympia”, entered the Irish album chart at Number 10. For the second year in a row Damien won Best Irish Male at the 2007 Meteor Awards. His fourth studio album, “To Hell or Barbados”, released world-wide in June 2007 entered the Irish album chart at number two. Once again, Damien was nominated in two categories of the Irish Meteor Awards 2008 and walked away as the winner of Best Folk/Traditional.

“The Rocky Road” was released in June 2008 and entered the Irish charts at number two. ‘Party On – Live at Vicar Street’ was released on DVD in 2008 and went straight to number one in the Irish Music DVD Charts. His sixth studio album, Almighty Love, was released in October 2012 and entered the chart at No. 3, with the single of the same name released in mid-October.

In 2014, Dempsey released a best-of album titled It’s All Good which entered the chart at No. 1. During the Australian leg of his tour promoting this album, he appeared on an episode of the comedy-music panel show Spicks and Specks. In 2016, Dempsey released an album titled No Force On Earth of original and covered songs to commemorate the centenary of The 1916 Rising. The album featured the traditional song “James Connolly” which Dempsey had become known for singing at recent protests to water charges introduced by the Irish government. Other songs on the album included one written for his great aunt Jennie Shanahan who fought in the 1916 rising along with a song to commemorate an ancestor of his friend, Love/Hate actor John Connors, who also fought in the rebellion. The album was initially only made available to buy at live concerts with a limited run of 2016 copies only being produced. His latest release in 2018 ‘Union’ – “Dempsey has managed to stamp his boots over more than just tradition. He engages with pop, reggae, hip hop and spoken word, all of which inhabit a place that you’d really need to describe as Damo Town.”