Tracy Chapman - Fast Car

Release date: 1988 
Chapman (from Q magazine): "It's not really about a car at all... basically it's about a relationship that doesn't work out because it's starting from the wrong place." This won the Grammy Award in 1989 for Best Female Pop Vocal Performance.
Rolling Stone ranked the song number 167 on their list of the 500 Greatest Songs of All Time. It is Chapman's only song on the list (and the highest ranking song both written and performed by a female artist). Pitchfork Media placed the song at number 86 on their list of the 200 Best Songs of the 1980s.
Album: Tracy Chapman