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Keelaghan studied history at the University of Calgary and two of his influences there were Drs. Margaret J. Osler and Silverman. With an international following in Australia and England, Keelaghan plays a wide variety of venues from large festivals and concert halls to intimate folk clubs venues and often invites the audience for a beer after his performance.
In 2003, Keelaghan won first prize (Folk Category) of the 8th Annual USA Songwriting Competition. In 2004, he was the recipient of a Juno Award.