The Top 10 List of Boston moments in David Letterman history
David Letterman has graced late night screens since 1982, but on Wednesday, May 20, the 68-year-old funnyman will sat behind the desk for one final show.
In his lengthy history of laughs and conversation, Letterman welcomed many Boston personalities to his set. In classic Late Show fashion, here are the top 10 Boston moments in David Letterman history.
10. Boston Celtics Celebrate Another Ring
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After the championship run of 2008, Ray Allen and Kevin Garnett took to The Late Show to celebrate their victory. Letterman’s disdain for Boston sports sometimes has a knack for creeping into his commentary, but his chat with Ray and KG was earnest, as the host even likens the Lakers to dental hygienists.
9. Barbara Walters Asks the Tough Questions[fragment number=1]
Barbara Walters has asked just about every question in the book to just about every celebrity of the past few decades. But when Letterman invited her by the show to partake in the famous Top 10, Walters found herself asking some, er, introspective questions.
8. Top 10 Red Sox Team Rules
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Actress Teri Garr doesn’t have much of a connection to Boston, but Letterman still enlisted her to read the Top 10 “Boston Red Sox Team Rules’’ back when he was still on The Late Show. Keep in mind, this was 1989, a time when there was unrest in the Sox clubhouse stemming from Wade Boggs. Leave it to Letterman to get some slightly questionable jokes out of it.
7. Belichick Mumbles About Deflategate
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Nobody in the world gives a worse interview than Bill Belichick. Stir in some Deflategate jokes from David Letterman (a diehard Colts fan), however, and you’ve got a supremely awkward conversation.
6. Amy Poehler Locks Lips with Letterman
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The Newton-born actress stopped by The Late Show just before hosting the Golden Globes with Tina Fey. After Poehler tells a story of sneaking a smooch in with Joe Biden, Letterman goes in for a kiss as well.
5. David Ortiz Tells Letterman Whose City it Is[fragment number=5]
After the 2014 World Series win, Big Papi made the trip to The Late Show to chat about the team’s resilience after the Boston Marathon bombings, and his famous words that motivated the city after tragedy.
4. Matt Damon Shamefully Wears Black and Gold[fragment number=6]
Local boy Matt Damon didn’t look too pleased sporting a New Orleans Saints jersey to the set of The Late Show. He goes on to tell the story of how he lost a bet, and how his make-good was to wear the jersey to the interview.
3. Conan O’Brien Makes a Triumphant Return
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Brookline’s Conan O’Brien returned to The Late Show in 2012 after the whole talk show “mix-up’’ that took place between him and Jay Leno the year before. The awkwardness of the situation was eased almost instantly as the two joked about it for upwards of 20 minutes. Letterman’s true feelings about Leno creep their way into conversation, too…
2. Kevin Spacey’s Two Beloved Bostons
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One of the greatest Boston moments in Letterman history came from an actor that isn’t even from the area. Kevin Spacey tells a heartwarming story of his trip to the city after the Marathon bombings, and how he ended up returning home with a puppy that he aptly named Boston.
1. Letterman Welcomes Leno for a Final Appearance
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There’s a bit of a chilling feeling that comes with watching Boston-bred comedian Jay Leno make his final appearance on The Late Show with David Letterman. Letterman essentially introduces Leno as the new host and Johnny Carson’s replacement on NBC’s The Tonight Show, a role that many had assumed Letterman would have been landed. Even at the time, the interview was awkward, but it’s even more so all these years later, as Letterman would end up leaving NBC shortly after, and in time, would not be shy about expressing his feelings toward Leno.
Fellow hosts bid farewell to Letterman
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