Michael Dean was born to parents from County Mayo near the Canadian border amidst the forests of northern New York state. His mother sang and, when he began logging work as a teenager, Barney Murphy and other bunkhouse singers he met gave him more songs. Dean logged in Michigan and settled in Pine County, Minnesota where he became a saloon keeper. When Prohibition came, he moved to Virginia, Minnesota to work as night watchman for a huge lumber mill. In 1922, while living in the flea-ridden Pine Tree Inn outside the front gate, Dean self-published a songster titled The Flying Cloud and 150 Other Old Time Poems and Ballads: A Collection of Old Irish Songs, Songs of the Sea and Great Lakes, The Big Pine Woods, The Prize Ring and Others. The book contains 166 songs from his repertoire, is one of the earliest collections of woods songs and demonstrates the popularity of Irish songs in the region. Dean corresponded with collectors Franz Rickaby and Robert Gordon who individually visited him in the 1920s, making transcriptions and cylinder recordings. A copy of his book made it to Irish collector Sam Henry who may have been inspired by its broad scope.