Song #1 - American Pie - Don McLean

Clocking in at 8 minutes and 32 seconds, American Pie is a rather controversial song which has been parodied by the great Weird Al.
Apart from the musical simplicity of the song, American Pie gives a good, although veiled, look at the musical and partly social arena of life in the early to mid 60s.
Written about a fatal plane crash in 1959 which killed Buddy Holly, Jiles Perry Richardson, Jr., and Ritchie Valens, the lyrics are all metaphorical in some sense.
There are multiple websites and videos devoted to explaining the nuances of the song, so I'll let y'all find that on your own if you so wish.
In any event, with a catchy chorus, the clear, clean vocals of Don McLean, and status as the fifth Song of the Twentieth Century, American Pie is a must-listen.