Sky Sailing adalah proyek solo pertama Adam Young pada tahun2006 sebelum ia memulai karirnya sebagai Owl City pada 2007. Sky Sailing merilis album bertamanya yang berjudul An Airplane Carried Me to Bed pada 13 Juli 2010 dengan single unggulan yaitu brielle sebelum ia melakukan tur sebagai Owl City. Setelah merilis An Airplane Carried Me to Bed Young mulai mendiskripsikan koleksi di situs Sky Sailing.

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I've kept these recordings secret for a long time and they've never seen the light of day until now. Long before Owl City was ever a spark of a flame, a lot of blue-collared working days were spent absentmindedly daydreaming about what would ultimately become this collection of songs. From the perfectionist musician's perspective, a song is never truly 'finished' but rather 'abandoned' and thus, after a lot of inspiration and reckless experimentation, I emerged from the basement with an 11 song record which I affectionately entitled, An Airplane Carried Me To Bed." - Adam Young

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