The Vince Guaraldi Trio – A Charlie Brown Christmas (1965) and Peanuts Greatest Hits (2015)

As one of the most acclaimed and beloved Christmas albums of all time, jazz pianist Vince Guaraldi mixed childlike wonder and post modern sophistication together for his soundtrack of the classic holiday special “A Charlie Brown Christmas.” A look at the special relationship between Vince Guaraldi and the world of Charles Schulz’ “Peanuts,” and how he created the perfect soundscape, as well as modern holiday classics, for Charlie Brown, Snoopy and all their friends. Extra: “Cast Your Fate to the Wind,” “Linus and Lucy,” “Little Birdie” and the problematic “Christmastime is Here” sessions.

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!

David Seville and The Chipmunks – Let’s All Sing with the Chipmunks (1959) and Christmas with the Chipmunks (1962)

Anyone who ever owned an album by Alvin and the Chipmunks remembers their manager/producer David Seville, but who was Ross Bagdasarian? The man behind one of the most enduring musical franchises of all time, Bagdasarian had a massive year in 1958 when he had two back to back number one Billboard hits – “The Witch Doctor” and “The Chipmunk Song (Christmas Don’t Be Late)” and unleashed Alvin, Simon and Theodore on an unsuspecting public for the first time! A look at the continuing legacy of “The Chipmunk Song (Christmas Don’t Be Late)” and The Chipmunks’ rise to fame! Extra: The Christmas that The Chipmunks teamed up with Canned Heat!