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The band’s debut album ...Waltzing Alone was self-released to immediate critical acclaim in Ireland on September 9, 2005, and their first promotional single “Told You So” rapidly climbed to No. 12 on the Irish National Airplay Chart.

In 2006, and again in 2009, the band performed at SXSW. They released ...Waltzing Alone in the U.S. on New York-based new model indie label United For Opportunity on September 26, 2006, and in November of that year embarked on their first U.S. national tour. Early in 2007, The Guggenheim Grotto's "A Lifetime In Heat" won The 6th Annual Independent Music Award for Best Folk/Singer-Songwriter Song.

The band has since completed four U.S. tours. Songs from their first album have been used in major network prime-time TV shows like One Tree Hill andBrothers And Sisters, and the album received positive reviews from U.S. national publications like Paste Magazine, as well as regional press like The Boston Globe and The Washington Post.

The band's second album, Happy the Man, was released digitally for a limited time in the U.S. and Ireland on October 7, 2008 and reached No. 1 on the U.S. iTunes Folk Chart. The CD was released to stores January 27, 2009, and the band toured nationally to support it.