1. “Christmas Time is Here,” Vince Guaraldi (1965) Ironically, anonymity saves this popular song from becoming clichéd. Everyone’s heard the melancholy tune in A Charlie Brown Christmas Special, but Guaraldi remains a bit of an unknown. Still, it’s a classic, because, like most great ballads, it occupies the threshold between joy and sadness.
2. “Sleigh Ride,” Ella Fitzgerald (1960) Can any modern singer keep up with Ella’s resolute coolness, the way she takes the reigns of this rollicking song and stylishly, wittily, effortlessly cruises through it? We doubt it. Like enjoying a sleigh ride with a hot toddy in your hand.
3. “The Christmas Song,” Dexter Gordon (1970) Listening to Gordon’s tenor sax is like greeting a gruff but lovable uncle who shows up at the holidays, the bristles of his beard rubbing against your cheek. His smoky tone, on full display here, is as warm as that fire in the hearth.