Lisa Loeb "Stay"

If you were a teenage boy in the 1990s, chances are you had a crush on Lisa Loeb.  With her girl-next-door looks and patented throwback glasses, Loeb adorned the hearts of many hormonal teens in 1994.  Present company included.  Loeb burst onto the scene when her folksy tune "Stay (I Missed You)" appeared on the Reality Bites Soundtrack.  The song quickly shot up the music charts and landed on the #1 spot in 1994 despite Loeb not having a record contract.  It was a feat not accomplished again until a recording contract-less Macklemore (featuring Ryan Lewis) did it in 2013 with "Thrift Shop".