Letterman’s Favorite Magician by
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Jason Randal

Years ago, we attended a fundraiser for affordable housing (an ongoing dilemma) on Martha’s Vineyard. The evening began with a reception on a large property where the Clintons had stayed while he was still in office, then fanned out to smaller parties across the island for special dinners and entertainment. We attended a “magic” party…we had been clued in to request this event, as it would be special. We knew most of the people there, the venue was gorgeous, host and hostess most gracious and the mystery guest was incomparable. Our host had hired him for corporate events, so already knew his caliber of work.

Our hosts lived next door to David Letterman, who was a reclusive presence on the Vineyard. They had private beaches on Edgartown Great Pond. I would see him jogging while I was on my morning bike rides. He’d wave and I would wave back, but he didn’t participate on the charity circuit. He came to relax. He also had a place in Montana, for longer get-aways. He was still the king of late night when this transpired and his son was young, so the Vineyard was an easy, relaxing get-away from New York City. Letterman was friendly with his next-door neighbor, who brought Jason Randal over to meet him before that first event started. Letterman was truly fascinated.

It was time for Jason’s act. We could not believe what we saw. He did up-close magic with cards, mind games, sleight of hand. He was phenomenal, the best any of us had ever seen. Great patter, pleasant demeanor. He sat with us later and chatted. We were entranced. I can’t describe what I saw, but will include a video of a Letterman appearance, since Dave loved him too. Dave called him his favorite magician and would have Jason on to celebrate Dave’s birthday – a huge compliment.

The fundraiser happened for several years and our host brought Jason back. One year, Letterman came over to introduce him, then disappeared. That was extremely rare, as he just didn’t do such things. He gave a little monologue by way of introduction. One woman shouted something at him. His put-down: “Lady, I work alone.” He was in cargo shorts and a tee-shirt. But he was there to support Jason. High praise, indeed.

Here is a Vimeo clip of an appearance on the Letterman show doing his card tricks. Letterman is as amazed as we are. Amy Sedaris is the other guest.

Profile photo of Betsy Pfau Betsy Pfau
Retired from software sales long ago, two grown children. Theater major in college. Singer still, arts lover, involved in art museums locally (Greater Boston area). Originally from Detroit area.

Characterizations: funny, right on!


  1. John Shutkin says:

    I vaguely remember Jason Randal, Betsy, so thanks for the great clip. It reminded me of how he did “simple” tricks brilliantly. And I love the story about Letterman introducing him at the fundraiser. That said, when you mentioned that Letterman had “disappeared” after introducing Jason, I half-expected that he would magically (of course) reappear at the end of the show. But I guess he tricked everyone.

    • Betsy Pfau says:

      Randal stuck around and mingled easily with us, John. Letter was more of a recluse, though several of us at dinner last night said they’d seen him recently, driving around the island, beard flapping, in an open Jeep with not seat belt. Guess he can take more risks, now that he doesn’t have a show on TV.

  2. Wow Betsy, what a charming guy, and how clever to – supposedly! – give us the explanation and then trick us again!
    What fun!

  3. Marian says:

    Very cool, Betsy, and the video was a perfect addition to the story to show Jason’s talents. Glad you got to see him in person.

  4. Khati Hendry says:

    It sounds like you got a good tip and were treated to an extraordinary up-close magic performance! Well worth the participation in the charity event, and even more wondrous for being in-person and not on a screen. Great memory.

  5. Suzy says:

    That sounds like one of the best fundraisers ever! Glad you knew which smaller party to request. And what a great bit of inside info, that Letterman learned about this guy from his next-door neighbor on the Vineyard. Thanks for including the clip, that was truly incredible!

    • Betsy Pfau says:

      It was a great fundraiser, Suzy and we were all in awe! As you saw, my description couldn’t do him justice, so I’m glad I found a good clip which I could include, so you could all be equally amazed.

  6. Laurie Levy says:

    That clip of Jason on Letterman was amazing. How did he do that??? Thanks for sharing a truly magical experience.

  7. Nice story Betsy, rich in detail and proximity to celebrity. My guess is that Dave does not hang w too many close friends, that he is sort of anti social, and not real personable, except with his personal assistants. But at his peak, and for several years after, and before he made dropping watermelons 🍉 boring, he was the best. Brilliant. Did you ever see the daytime show he started with? Really loose as a goose in those early days.
    I bet those dinners were gala affairs.
    As to the magician, a good magician is phenomenal, I agree. I once was at a NYC party w a card magician entertainer who mesmerized me to the point of mind blow.

    • Betsy Pfau says:

      I suspect David is shy and doesn’t want his celebrity to get in the way of any real friendship. He and his Vineyard neighbor became real friends, as they respected boundaries. I never saw him on daytime TV, but would occasionally catch his late-late night show, when things were very loose, unconventional and brilliant. Just good fun.

      I agree, unclose magic, when well done can truly be mind-blowing.

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