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David Letterman Spotted At Duckworth Fundraiser in West Loop Tuesday https://t.co/A7jAMjp44c pic.twitter.com/bZbYf91FeF

— 365Chicago (@365Chicago) October 19, 2016

posted by Rich Miller
Thursday, Oct 20, 16 @ 1:51 pm

Comments

  1. Long beard, short tie, bad art? It all fits.

    Comment by A guy Thursday, Oct 20, 16 @ 1:55 pm

  2. TD: OK Dave, Lean in next to the money.

    Comment by A guy Thursday, Oct 20, 16 @ 1:56 pm

  3. Letterman: “Politics is easy. After all, I’ve been doing ‘Stupid Human Tricks’ for 30 years…”

    Comment by Ron Burgundy Thursday, Oct 20, 16 @ 1:58 pm

  4. Rep. Duckworth, pictured with a man with ridiculously fake hair and David Letterman.

    Comment by wordslinger Thursday, Oct 20, 16 @ 2:03 pm

  5. Which one is Letterman?

    Comment by Anon III Thursday, Oct 20, 16 @ 2:03 pm

  6. Duckworth posing with two of her policy advisors

    Comment by People over Parties Thursday, Oct 20, 16 @ 2:04 pm

  7. Larry Sanders still looks like himself, but Letterman on the other hand….

    Comment by Madigan's Lapdog Thursday, Oct 20, 16 @ 2:11 pm

  8. DL: Wait a minute. You’re not Chris Kennedy.

    Comment by A guy Thursday, Oct 20, 16 @ 2:14 pm

  9. “Paul Shaffer really cleaned up his looks; wouldn’t know him from the old days. Letterman looks like the bums he used to roust with the water cannon.”

    Comment by Arthur Andersen Thursday, Oct 20, 16 @ 2:15 pm

  10. David Letterman congratulates Congresswoman Duckworth on winning, “Best Art Project by a Congresswomen running for an Illinois Senate seat.” The runner-up was some guy in a suit worn by Jack Nicholson in the 1989 hit, “Batman.”

    Comment by Ahoy! Thursday, Oct 20, 16 @ 2:15 pm

  11. Letterman: “hi, Bill, I’m Dave.”
    Griffin: “actually, you can call me Senator.”

    Comment by Anon Thursday, Oct 20, 16 @ 2:16 pm

  12. And the number one sign Tammy Duckworth will be elected to the Senate is: because Santa Claus is voting for her too.

    Comment by 47th Ward Thursday, Oct 20, 16 @ 2:17 pm

  13. Drum roll please. And the number one reason Tammy won’t win the election, she is a former Rod Blagojevich cabinet member.

    Comment by pool boy Thursday, Oct 20, 16 @ 2:18 pm

  14. Santa Claus called in to bail out flailing campaign.

    Comment by NIU Grad Thursday, Oct 20, 16 @ 2:21 pm

  15. Letterman “Tammy, you know I had your friend Blagojevich on my show once. You want me to talk about him and how you are one of his people?”

    Comment by siriusly Thursday, Oct 20, 16 @ 2:27 pm

  16. Burl Ives….

    Comment by Anotherretiree Thursday, Oct 20, 16 @ 2:31 pm

  17. The eclectic cast of “A Very Confusing Christmas” poses for a quick pic before taping another segment. Mark Giangreco is rumored to be a Golden Globe candidate since abandoning Channel 7.

    Comment by Deft Wing Thursday, Oct 20, 16 @ 2:33 pm

  18. I thought it was Steve Brown at first glance.

    Comment by Indochine Thursday, Oct 20, 16 @ 2:37 pm

  19. Tammy Duckworth pictured with David Letterman and the man that represents everything she supposedly hates.

    Comment by Terrible Towel Thursday, Oct 20, 16 @ 2:44 pm

  20. Santa Claus and Billy Marovitz agree on two things: Playboy Magazine is awesome and Tammy Duckworth should be in the US Senate.

    Comment by 47th Ward Thursday, Oct 20, 16 @ 3:07 pm

  21. Dave, the Indiana border is over there. You cannot vote in this election. By the way, how is your new gig going? When will you be in the Santa Claus House for the holidays?

    Comment by Nearly Normal Thursday, Oct 20, 16 @ 4:07 pm

  22. HO, HO, HO!

    Comment by burbanite Thursday, Oct 20, 16 @ 4:18 pm

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