Written during The Beatles’ time studying Transcendental Meditation in India, “Dear Prudence” entreats one of their fellow students to “come out and play.” Who is that student’s more famous sister?

Neil Diamond was inspired to write “Sweet Caroline” by the daughter of what political family?

Pattie Boyd, the real-life Layla from the Derek and the Dominos hit was once married to one of Eric Clapton’s best friends. Who was Pattie’s ex-husband?

Don McLean’s “American Pie” commemorates the passing of Buddy Holly, Ritchie Valens and The Big Bopper. Who was the country music legend originally scheduled to be on that plane, but spared by a coin flip?

Later rewritten to eulogize Princess Diana, the original version of Elton John’s “Candle in the Wind” is about which blonde bombshell?

In 2000’s “Ms. Jackson”, Outkast's Andre 3000 never meant to make Ms. Jackson’s daughter cry. Who is the famous daughter?

Bob Dylan’s 1975 protest song “Hurricane” concerns the wrongful conviction of which 1960s boxer?

In 1985’s “Money For Nothing”, Dire Straits use some un-PC language to lament the success of which MTV icon?

Billy Joel’s 1983 hit “Uptown Girl” proclaims his love for what supermodel?

In 1992, Barenaked Ladies sang about artistic struggles and “lyin’ in bed” like which songwriter?

Alanis Morisette’s breakout hit “You Oughta Know” is the sordid story of her relationship with what 80s/90s sitcom supporting player?

Roberta Flack's version may be more famous, but Lori Liberman says the orignal “Killing Me Softly” expresses her feelings about the work of singer?

The song that launched a thousand movie trailers, Peter Gabriel’s “In Your Eyes” is an ode to which 80s actress?

In their 1992 single “Man on the Moon”, R.E.M. celebrate the career of which stand-up comedian?

Which grunge icon is Dave Grohl venting his anger towards in 1995’s “I’ll Stick Around”?

Written as a tribute to one of their own, “Shine on You Crazy Diamond” is about which Pink Floyd band member?

Madonna has had a number of famous romances, but who was the “True Blue” who inspired the 1986 single?

Writing songs about her exes is practically a Taylor Swift trademark. Which ex-boyfriend has apparently escaped this treatment?

Aerosmith’s “Dude (Looks Like A Lady)” is about a case of mistaken identity with which 80s glam metal lead singer?