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Tom Dunning made a name for himself by taking over Hoot Nights – themed multi-artist events – in Chicago.  A theme, two surprise cover songs from each act, cross-pollination of artists as often as possible and a whole lot of laughs.
He established his own vanity record label, Brown Star Records, and organised the Kate Bush tribute album I Wanna Be Kate in 1998, to which he contributed a cover version of Not This Time as Tom Dunning & Your Boyfriends (together with John Ridenour, Eddie Carlson, John Eichenseer and Liam Davis).

Dunning moved to Dublin, Ireland in 2002. He set up his Hoot shop and organised the same events in Dublin and Galway until 2013.

In 2020, Tom organized a new compilation entitled I Wanna Be Kate: The Songs Of Kate Bush – Remastered & Expanded, which was in fact a digital release with seven additional tracks when compared to the original I Wanna Be Kate release. On a vinyl 12″ single these seven tracks (plus a remastered version of Tom Dunning’s ‘Not This Time’) appeared. Tom Dunning & Your Boyfriends added a new cover version of the song Nocturn.