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".

Big Mountain - "Baby, I Love Your Way"

Shaggy, UB40, and Jimmy Cliff found commercial success by adding Reggae to classic American songs.  Add Big Mountain to that list as their saxophone-rich remake of "Baby, I Love Your Way" found itself on the Reality Bites Soundtrack and into the Top 10 in 1994.