Six of My Favorite David Letterman Interviews

As The Late Show with David Letterman comes to a close, signaling the end of thirty-three total years of Letterman’s hosting duties on that program (1993-2015) and Late Night with David Letterman (1982-1993), I would like to share five of my favorite interviews that Letterman has conducted during his decades as a late night talk show host. Network TV won’t be the same without his eccentric comedy. (I realize now, after compiling the list, that all of the guests I am showcasing are men, but my choices were not actively intended to exclude female interviewees.) Anyway, enjoy these wonderful clips!

Bill Murray was Letterman’s first-ever guest on Monday, February 1, 1982. For what it’s worth, Murray has lived up the promise he made that night: “I swear, Letterman, if it’s the last thing I’m gonna do I’m gonna make every second of your life from this moment on a living hell.” It has always been a treat to see Murray and Letterman together, including the penultimate show earlier tonight (well, since it is almost 5:00 AM now, I mean last night), during which Murray burst out of a “Goodbye Dave” cake and smothered Letterman in a crumb-filled embrace that left the host wearing a frosting beard.

In 1986, Tom Waits stopped by the Late Show to promote his recent album Rain Dogs and to discuss upcoming projects like the Jim Jarmusch film Down by Law and a theatrical adaptation of Waits’ song “Frank’s Wild Years” into a musical. Waits’ charmingly oddball sense of humor permeates every interview he has with Letterman, including his conversation with Letterman last week, after which Waits debuted a new song written especially for the occasion, “Take One Last Look.”

When people think of the combined terms “Joaquin Phoenix” and “Letterman interview,” they probably remember Phoenix’s infamous 2009 interview in which he was in the guise of Joaquin-Phoenix-the-actor-turned-rapper. The chat culminated in a brilliant send-off from Letterman, who had not been in on the joke: “Joaquin, I’m sorry you couldn’t be here tonight.” What I particularly love, though, is this 2010 interview in the video posted above, which was Phoenix’s first return to the show as his normal self to promote the mockumentary I’m Still Here (2010) about the ruse. Letterman fires some great lines at Phoenix for having duped him in that previous interview.

All things considered, Regis Philbin is my favorite Letterman guest. There is simply nothing better than their rapport, a true friendship that allows them to do things both silly (sharing laughs over ice cream) and serious (discussing what it means for a person to serve his or her country, including Letterman’s experience with the Vietnam War draft and lottery). It was hard for me to pick just one great example of Letterman and Philbin together; another lovely moment was when Letterman sat next to Philbin in the second guest chair rather than behind the desk and the two friends reminisced about old memories and even danced together a little.

Michael Shannon’s first interview with David Letterman, promoting the film Man of Steel (2013), was fun to watch because two months earlier I had read an interview with Shannon in New York Times Magazine that discussed his fervent hope to be interviewed on his favorite late night talk show: “How many movies do you gotta do to get on ‘David Letterman’? All I’ve wanted since I was 15 freaking years old was to be on ‘David Letterman.’ I mean, I’m in Man of Steel. I think they all think I’ll be violent.” Shannon did in fact get to go on the show to promote his summer blockbuster and he told some fun stories about getting started in show business too.

Every year for many years I looked forward to the annual telling of Letterman’s “favorite talk show story ever,” Jay Thomas’s remembrance of an encounter with “The Lone Ranger” (actor Clayton Moore) in Charlotte, North Carolina. If you’re looking for great entertainment, you’re not going to do better than Thomas’s tale, topped off by a terrific punchline. The other half of the holiday ritual is the game that Thomas and Letterman play of using footballs to try to knock a meatball off the top of a Christmas tree. It’s goofy traditions like these that I will probably miss the most when December rolls around.

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The Week That I Became a Fan of Tom Waits

It was a week ago that I officially delved into the wild, genius world of Tom Waits. God only knows what force it was that drove me toward his music (the influence of friends? or was it when I found out that my favorite movie house, the Museum of the Moving Image, will be showing Down by Law next month?). All I know is I’m now a fan and I’m so, so glad.

I started out by listening to all of The Heart of Saturday Night, Waits’ 1974 record which is ranked among the 500 greatest albums of all time by Rolling Stone. In a way it’s misleading to become too attached to this iteration of Waits’ voice since he would soon begin to sing in the guttural tones that have become his trademark (a style which is appealing but in varying degrees). Even so, “Fumblin’ with the Blues” is a highlight of a near-perfect album. I dig it.

“A Sweet Little Bullet from a Pretty Blue Gun,” which appeared on Waits’ 1978 album Blue Valentine, is performed here in concert. If jazz and blues are your cup(s) of tea, then you might love this sound. It seems to me that Tom Waits engenders extreme reactions from listeners: you might be obsessed with his gravel-throated rasp or you might think it’s the worst thing you ever heard. Your decision.

Tom Waits has been on “The Late Show” many times in the last thirty years but this is possibly my favorite appearance. Performing “Tango Till They’re Sore” and “Time” from Rain Dogs (1985), another of those “greatest albums of all time,” the songs are punctuated by a interview. You don’t often find musicians who are actually so engaging, even when being – dare I say it – weird. Embracing individuality, introversion, awkwardness: it works for Tom Waits. You can tell that David Letterman is a genuine fan.

Bonus (if you’re still hanging in there): “Temptation” from Franks Wild Years (1987). One Internet description: “like Prince with emphysema.” It’s very lounge lizard-y. As a music video from MTV’s golden age of Madonna and George Michael, Waits’ off-kilter, sort of bizarre musical choices stand out. It would take far too long for this one post to further explore the next half-century of Tom Waits’ discography, but feel free to go for it on your own. You’re not likely to find anyone else quite like him.