The Pogues – If I Should Fall From Grace with God (1988)

“Fairytale of New York,” by The Pogues has become the favorite Christmas song for people who hate Christmas songs. A duet between lead singer Shane McGowan and singer/songwriter Kirsty MacColl, its equally beloved and controversial for its combative delivery and blunt lyrics. But while her voice has become iconic for her important part in the song, Kirsty MacColl’s story seems to be overlooked by the audiences who play this favorite each year. We look at the life and career of Kirsty MacColl, and the heroic sacrifice that took her life during a Christmas holiday in 2000. Bonus: How Kirsty MacColl helped Tracy Ullman hit the top of the charts!

Paul McCartney – Give My Regards to Broad Street (1984)

At the age of nine future record collector Sam Tweedle brought a copy of Paul “McCartney’s “Give my Regards to Broad Street” home from a school fun fair which opened the doorway into the music of The Beatles, although he didn’t know it. One music fan’s misstep into the music of McCartney, and a look at his early 1980’s MTV period and his hit single “No More Lonely Nights.” Extra: The importance of McCartney and Michael Jackson’s collaborations on the MTV generation.

Frank Sinatra – Trilogy: Past Present Future (1980)

In 1980, to celebrate his 40th Anniversary, Frank Sinatra blasted off into outer space for a kooky intergalactic song cycle called “The Future” on his album “Trilogy: Past Present Future.” A divisive recording amongst critics and fans, it’d be the biggest recording session of Sinatra’s career. A look at this bizarre entry into the Sinatra songbook. Extra: The release of “New York, New York” and how it recentered Sinatra’s legacy.