24. "Pretty Paper," Roy OrbisonMonument 803 b/w "Beautiful Dreamer"
Highest chart position: #15 US (1963), #6 UK (1964)
Recorded September 1963, Nashville, TN
Trust Willie Nelson, then a successful songwriter but relatively unknown performer, to pen a Christmas classic that puts the focus on those who can't afford the basic luxuries of the season; trust the Big O, then in his monumental Monument prime, to make the sentiment seem holiday-friendly anyway. Of course, the first verse is a red herring that shuts your mind off: "Pretty paper, pretty ribbons of blue / wrap your presents to your darling from you," but we can also thank / blame that big countrypolitan sound for lulling us into complacency. Then again, when you finally do discover the message, the pretty aural paper around this package gives the song much of its ironic thrust.