By Paula @ Holiday World

It’s time to climb into our way-back machine.


It’s August 6, 1995.

Twenty years ago.

Two decades.

A score.

Hot as blazes here in Santa Claus.

The Raven is new and it’s a hit.

And it’s a Sunday afternoon. Will passes along a call from two very excited local teachers.

Letterman ticketThey’ve got tickets to Letterman.

And they want “stuff” to take with them to New York.

Not being a late-night person, it took me a while to interpret their rather odd request.

I knew one of the teachers (best first-grade teacher ever!) and would come to know the other (best high-school English teacher ever!). Betsy and Elaine were Letterman fans of the highest order. And they had a plane to catch.

Dave himself is from Indiana, so it was time to step up and provide gifts for the King of the Late Show. And we had about 20 minutes to make it happen.

Betsy and Elaine (and Will) were convinced that proof that their hometown was Santa Claus, Indiana, would capture the attention of the gap-toothed star.

And so, I rather begrudgingly parted with my two-and-only Santa hats. I liked those hats. I used those hats. Why couldn’t Dave buy his own Santa hats?

“Bring them back safely!” I called, as the teachers dashed off to catch their plane. I meant my Santa hats, of course.

Betsy and Elaine’s ultimate goal, it seems, was threefold.

It had to do with a canned ham.

And a deli named Hello.

And getting Dave to notice them.

I believe they accomplished just that:

Amazing, right?

Betsy and Elaine were literally picked out of the line as they were waiting to get in to see the Late Show.

It was a Christmas wish come true!

Elaine, Rupert Jee from Hello Deli, Betsy, and the coveted canned ham

Elaine, Rupert Jee from Hello Deli, Betsy, and the coveted canned ham

And so, as Dave retires this week, we have just one final question for the Hoosier-born host:

Letterman Santa Hat What did you do with those Santa hats? I still want them back!

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6 Responses to “The Letterman racket”

  1. Joe

    Totally awesome. Believe it or not, i vaguely remember that show, that night. Letterman has always been my second favorite. Behind Carson, of course.

  2. LeisaMcWhorter

    Love love love David Letterman, grew up in Indiana also !!! Sad to see him retire !!!!

  3. Elaine Daubenspeck

    Thanks for the hats (sorry we didn’t bring them back ????) and thank you especially for this wonderful walk down memory lane!! Really going to miss Dave and The Late Show!! ????

  4. Shirley Blazey

    Great Flashback. Good Luck getting the hats back. Thanks for the memory.

  5. Betsy

    hey, Paula–What a trip down Memory Lane! Your article is great. Thank you so much! love, betsy

  6. Matt beatty

    that’s how Santa Claus Indiana became famous for its renowned amusement park call Holiday World from the cook family.I wouldn’t know what to do if the cook family would sell the place and it was not in the family. the cook family is amazing family when it started from a son, dad, grandfather, great grandfather and a friend.