The Most Wonderful Night of the Year (2018 edition)

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Originally published in The Huffington Post in 2008

There is a great American holiday tradition that flies under the radar annually. It’s not only funny, but heartwarming and wildly entertaining.

Every December 23rd, or the last weeknight before Christmas Eve, Late Night with David Letterman celebrates the holiday season with a special show that is not advertised or hyped. This show feels like a secret Xmas gift from Dave and the gang to me. I love this show as much as anything I’ve ever watched on TV.

While the longstanding traditions of the show don’t sound like much in isolation, taken together they make one of the most rewarding hours of television each year.

After the monologue and usual opening bits, the festivities begin in earnest when Dave pleads with Paul Shaffer to do his impression of Cher singing, “Oh, Holy Night,” just like she did on a Sonny and Cher Christmas Special, featuring guest star William Conrad, more than thirty years ago.

The impression is as absurd as the hilarious details setting up the historic musical recreation. Dave laughs with the joy known to lifelong buddies who can cause each other to burst into hysterics with the motion an eyebrow or the mention of one word.


1999 Performance


1983-1992 Compilation


The original

Next, actor/comedian/radio host/raconteur, Jay Thomas comes out to fulfill two sacred holiday traditions.

1) Jay Thomas tells the story of being a young long-haired “herbed-up” North Carolina DJ working a promotion at a car dealership and the ensuing car accident involving the Lone Ranger. The story gets better every year with each retelling. Once again you share Dave’s glee.


The first time Jay Thomas told the legendary story in 1998.


The final time Jay told the Lone Ranger Story


A couple more classic retellings for good measure

Jay told the story every year for decades. In 2012, Jay could not make the show. So in a surreal twist, John McEnroe stepped in to tell the story in his place.

In 2011, the story included “video of the original event.”

2) Following the retelling of the Christmas tale, Jay joins Dave in a challenge of throwing a football to try and knock the meatball off the top of the Christmas Tree. It doesn’t matter why there is a meatball at the top of the Christmas tree, all you need to know is that in 1998 Dave had NFL quarterback Vinny Testaverde as his guest. It was the night before Christmas (Eve) and Dave challenged Vinny to knock the meatball of the tree. After repeated failed attempts by both Dave and Vinny, Jay Thomas, waiting in the green room to come on the show ran out on the stage, grabbed a ball and triumphantly hits the meatball with his first shot. Henceforth, a holiday miracle gets repeated each year.

Rest-in-Peace Jay Thomas (1948-2017)

Each year, the telecast ends with Darlene Love and a large ensemble singing Christmas (Baby Won’t You Please Come Home). Love brings down the house with the song from the classic album, A Christmas Gift to You from Phil Specter. Each year, Paul and Dave argue that this is the greatest Xmas song ever. They may just be right.

Every performance from 1986-2014. It starts during the 1998 performance when Cissy Houston, Roberta Flack, and Phoebe Snow sang backup vocals.

The final appearance in 2014

My gift to you is a reminder to set your TIVO, DVR or VCR for CBS at 11:35 PM on December 23, 2008.

Have a safe, happy, healthy and musical holiday filled with joy!


Sadly, The Late Show with David Letterman is no longer on the air. So, the annual celebration I write about above is no longer broadcast on television. As a consolation prize, here are two long lost Letterman Xmas classics in their entirety.


Also published on Medium.

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