1. Holidays on Ice by David Sedaris
If you like Sedaris and his droll sense of humor, you probably already consider this collection of short stories a classic. If you don’t like Sedaris, I don’t know if there’s anything in here that will change your mind. But if you haven’t read any Sedaris, then SantaLand Diaries–the story of a 33-year-old man working as an elf at SantaLand–is a great point of entry.
2. A Different Kind of Christmas by Alex Haley
Haley’s best known as the author of Roots and the ghostwriter of Malcolm X’s autobiography. That sort of resume doesn’t immediately make one think of Christmas. However, A Different Kind of Christmas is true to both the season and Haley. It tells the story of a young man who’s trying to help one of his father’s slaves escape on Christmas Eve.
3. A Christmas Carol by Charles Dickens
You know this one: stingy lender, hobbled child, three ghosts, humbug. Even if you’ve seen a half-dozen movie versions of this story, you should still read the book. It has some of Dickens’ finest writing. (And, if you’re looking for a movie version, my personal favorite is the Muppets.)
4. A Christmas Memory by Truman Capote
Let’s be honest. It’s easy to make Christmas stories (especially those involving children) saccharine. But this story about a 7-year-old boy and an elderly woman, who is also his best friend, hits the sweet spot. It’s a beautiful rumination on odd friendships and growing up.
5. Mrs. Miracle by Debbie Macomber
Even if you don’t know Macomber by name, you probably still know her stories. She’s responsible for the stories behind several Hallmark films. If you enjoy Hallmark films, you’ll love Macomber’s books. If you don’t, there’s always Holidays on Ice.
6. Matchless by Gregory Maguire
Maguire–the writer behind Wicked and Confessions of an Ugly Step-Sister–gives his version of the Hans Christian Andersen’s The Little Match Girl. Fair warning: You’ll probably cry when you read this (but you already know that if you’re familiar with the original.)
7. You Better Not Cry by Augusten Burroughs
Burroughs was on his sixth memoir by the time he wrote You Better Not Cry. That’s even more than Winston Churchill. You would think Burroughs would be out of material by now, but his Christmas-tinged recollections range from sweet to sad and never miss their mark.
8. Winter Dream by Richard Paul Evans
You were expecting The Christmas Box, right? That’s his stadium hit, his Layla or Stairway to Heaven. But Evans has written a lot of seasonally appropriate tomes. This one incorporates the Old Testament story of Joseph and his prophetic dreams and gives it a modern retelling.
9. Polar Express by Chris Van Allsburg
Don’t let the dead-eyed motion-capture movie deter you. This story is a classic.
10. Decked With Holly by Marni Bates
This YA book about a girl pretending to be fauxmantically involved with a mega-popular rock star is over the top in all the right ways. Teens who liked Bates’ Awkward will get a kick out of Holly too.
11. Santa & Pete by Christopher Moore & Pamela Johnson
Did you know that Santa used to have an African accomplice named Pete? You know about the elves and Rudolph; but, somehow, Santa’s most important helper has disappeared in the annals of time. (If you liked Moore’s story about Jesus’ forgotten friend Biff, then you’ll get a kick out of this too.)
12. How the Grinch Stole Christmas by Dr. Seuss
Most people think the instance where the Grinch’s heart grows three sizes is a nice moment. But cardiomegaly can lead to congestive heart failure. It may have even contributed to Secretariat’s death.
That aside, this book is pretty much perfect. I read it every Christmas… and Easter… and most Octobers… and sometimes in June.