- 1. Uptown Girl
Written by Billy Joel about his then girlfriend/model Elle Macpherson. A couple years after their breakup, he dedicated it to his fiance, Christie Brinkley.
- 2. Something
Written by George Harrison about girlfriend Pattie Boyd.
- 3. Wonderful Tonight
Written by Eric Clapton about girlfriend Pattie Boyd (after her split with Harrison).
- 4. Miles Away
Written by Madonna about Guy Ritchie just months before the two decided to get a divorce.
- 5. In Your Eyes
Written by Peter Gabriel about girlfriend Rosanna Arquette (also the subject of the song Rosanna, by Toto).
- 6. You Oughta Know
Written by Alanis Morissette about ex-boyfriend Dave Coulier.
- 7. Killing Me Softly
Although this song was made famous by Roberta Flack, it was written by folk singer Lori Lieberman about Don McLean.
- 8. Maybe I’m Amazed
Written by Paul McCartney about his then wife Linda.
- 9. Hey Jude
Although Jude exists solely in this famous song, Paul McCartney was inspired to write it after a car ride with John Lennon’s son Julian (nicknamed Jules) who was having a hard time coping with his parents’ divorce.
- 10. Philadelphia Freedom
Written by Elton John about his friend Billy Jean King, a professional tennis player.
- 11. Kooks
Written by David Bowie for his newborn son Duncan. When he got the news of his son’s birth, he was apparently listening to Neil Young and credits Young with the musical styling of this song. Bonus: The Kooks named their band after this song.
- 12. Chelsea Hotel #2
Written by Leonard Cohen about his brief affair with Janis Joplin.
- 13. Sweet Child O’ Mine
Written by Guns N’ Roses frontman Axl Rose about his then girlfriend Erin Everly.
- 14. Terry’s Song
Written by Bruce Springsteen about his recently deceased assistant and close friend, Terry Magovern.
- 15. My My Hey Hey (Into The Black)
Written by Neil Young about the “death” of Johnny Rotten, the stage name for John Lydon of the Sex Pistols. Bonus: The lyric “It’s better to burn out than to fade away” was quoted in Kurt Cobain’s suicide note.
- 16. You Haven’t Done Nothin’
One of two songs written by Stevie Wonder about his disappointment in former president, Richard Nixon.
- 17. Tramp The Dirt Down
Written by Elvis Costello about Prime Minister Margaret Thatcher.
- 18. Englishman In New York
Written by Sting about English writer and raconteur, Quentin Crisp.
- 19. Angie
Although it is rumored that this song was written about Angie Bowie (wife of David Bowie), it was written by Rolling Stones’ member Keith Richards about heroin and his detox in Switzerland after the birth of his daughter, Dandelion Angela.
- 20. Hurricane
Written by Bob Dylan about Rubin “The Hurricane” Carter, a professional boxer who was convicted of triple homicide in the late 1960’s.
- 21. Just Like Anyone
Written by Aimee Mann about the death of her friend and fellow singer/songwriter, Jeff Buckley.