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"Stupid Stupid" is Day's third attempt to get into the charts by utilising the internet. In 2009, Day was part of the Chartjackers project, which charted at number 36 in the UK. In 2010, Day was part of the collective "Sons of Admirals" along with three other YouTubers. The group's cover of Cat Stevens' song "Here Comes My Baby" peaked at No. 61 in the UK Singles Chart. In 2011 he released Forever Yours which was his best attempt so far, peaking at No. 4 in the UK Singles Chart.
Music video
A music video to accompany the release of "Stupid Stupid" was first released onto YouTube on 5 December 2012 at a total length of two minutes and fifty-six seconds. The music video was directed by Ciaran O'Brien and stars Day's family.