1995: Radiohead - Fake Plastic Trees
1996: OutKast - 13th Floor / Growing Old
1997: Modest Mouse - Bankrupt on Selling
1998: Neutral Milk Hotel - In the Aeroplane Over the Sea
1999: The Roots - You Got Me
2000: Yo La Tengo - Our Way to Fall
2001: The Microphones - The Moon
2002: The Mountain Goats - Old College Try
2003: The National - Lucky You
2004: Kanye West - Family Business
2005: Why? - Gemini (Birthday Song)
2006: Destroyer - Your Blood
2007: of Montreal - The Past Is A Grotesque Animal
2008: Deerhunter - Agoraphobia
2009: The Antlers - Two
2010: Sufjan Stevens - Impossible Soul
2011: Car Seat Headrest - Beach Life-in-Death
2012: Frank Ocean - Thinkin Bout You
2013: Rhye - The Fall
2014: D'Angelo and the Vanguard - Really Love
2015: Kendrick Lamar - Wesley's Theory
2016: Car Seat Headrest - Cosmic Hero
Some of these I'm not really sold on, and I'm sure I'd pick different songs on different days, but these made sense to me tonight so yeah there you go.