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May 20, 2015
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We chose our favorite David Letterman moments from Dave's run as host of the Late Show. From interviews with Paris Hilton, Joaquin Phoenix, and Amy Sedaris to his greatest hits like 'Strong Guy, Fat Guy, Genius' and 'Top Ten,' these are the Letterman gems that made us laugh the most.

After more than three decades of his sly smiles and sardonic humor, late night TV just won’t be the same without David Letterman. With Dave’s final Late Show airing tonight, we asked the Funny Or Die writers to choose their favorite moments from Letterman’s monumental career.


“Are Those Your Drums?” Compilation

Nate Dern: The “Are Those Your Drums?” compilation video isn’t exactly a single moment, but I think it is my favorite Dave Letterman thing I can think of. This is a montage of all of the moments when Dave walks over to a band after they’re done playing and asks them about their instruments. It’s while the audience is still applauding from the end of their song and a lot of the time just feels like a private moment that Dave was just doing for Dave.


Letterman Goes Door-to-Door with Siskel & Ebert in New Jersey

Ryan Perez: David Letterman has been leaving his studio since his earliest days at Late Night, but after moving to CBS, his remote pieces became even more ambitious and snappily edited (see Letterman traveling door-to-door with Richard Simmons or eating fast food with Zsa Zsa Gabor to see a lean and mean Letterman at his Late Show peak.) In later years, Dave left the traveling duties to stage manager Biff Henderson, who proved an inspired choice in his memorable segment, Biff Henderson’s America. Of all Letterman’s adventures outside the studio, this door-to-door trip to a New Jersey suburb with Gene Siskel and Roger Ebert just might be the most worth revisiting. It features Letterman and two of his favorite guests, both now long gone, spending some quality time with regular folks. Nothing too flashy about this segment, but it seems like Letterman got a genuine kick out of the day.


David Letterman Questions Paris Hilton About Jail

Fran Gillespe: Letterman doesn’t suffer fools. In the last 10 or 15 years American culture has been inundated with so many people who have gained fame and notoriety not from having talent, but for being attractive or wealthy or reveling in their ability to be entirely unlikeable. Watching Letterman interview guests he has absolutely no interest in or respect for makes me cringe and squirm and cover my eyes, but there is truly nothing more entertaining. The way Letterman maintains his integrity and gets his point across to his loyal audience while still respecting his guests reminds me of the way children’s shows include jokes for the adults watching.

Zack Poitras: This is his interview with Paris Hilton after she spent a short time in jail. It’s a great example of Letterman caring more about making himself and the audience laugh than keeping a guest he didn’t respect happy.


Where’s Joaquin Phoenix?

Amos Vernon: Ooh baby the Joaquin Phoenix interview is a classic. The quantity of zings he generates on the spot is incredible. “I’m sorry you couldn’t be here today” is a legendary, A+ dig.


Amy Sedaris

Fran Gillespe: When Letterman has a guest on that truly makes him laugh it fills me with a red hot jealousy. Letterman doesn’t give anyone a polite laugh; he either laughs or he doesn’t. The way Letterman laughs when Amy Sedaris is on his show, and you should watch all her appearances, infuriates me because you can tell that he really loves this little weirdo and honestly, who couldn’t? Amy talks about her imaginary boyfriend, her rabbits, she brings in crafts that you would never make at home, and Letterman loves every second of it. Sedaris is so unique and strange and manic and Dave gives her a platform to be herself and so, I will reluctantly admit, Amy deserves all of Dave’s attention.


Casey Kasem Top Ten

Zack Poitras: This is “The Top Ten Numbers Between 1 and 10,” with special guest Casey Kasem. I’m not going to explain why I like it.


Future Islands: “Seasons (Waiting On You)”

Zack Poitras: And here’s a third one just to cheat even more, it’s Future Islands performance of “Seasons (Waiting On You).” Dave’s reaction at the end is great: “Oh yeah, I’ll take all of that you got.”


Dave’s Drive Thru

Jason Flowers: Although he hasn’t left the studio much in the last few years, my favorite Letterman moments always happened outside the theater. Put simply, there’s nothing better than Dave interacting with regular people. Two of my favorite clips are of Dave working the register at big-time fast-food restaurant chains.

Whenever I watch these, which is honestly pretty often, I imagine a scenario where everything went wrong in Dave’s life. No comedy career, no talk show, no $30 million–a-year salary, yet he’s being the exact same type of asshole he’s always been on TV. I smile just thinking about it.


Dave Responds To Jay’s “Don’t Blame Conan”

John Harris: This one’s kind of obvious, but Letterman weighing in on the whole Conan O'Brien/ Jay Leno fiasco in 2010. Mad Dave is my favorite Dave.


Interviewing Bill O'Reilly

Pat O'Brien: I always liked Letterman’s interviews with Bill O'Reilly, mainly because they’re just such exciting TV. Dave gets really fired up and calls O'Reilly out for being a snake-oil salesman, repeatedly accusing him of peddling political and social views that he (Bill) is too smart to actually believe himself. Dave is a master interviewer and has a great knack for cutting to the core of what is actually interesting about a particular guest (like when he wouldn’t let Paris Hilton’s jail stint drop because he knew that was what he and the audience found most interesting about her at the time), and in the case of O'Reilly, he refuses to let Bill get away with his Culture Warrior schtick without appropriately taking him to task for it.


The Strong Guy, The Fat Guy, The Genius

Pat O'Brien: And here is “The Strong Guy, The Fat Guy, The Genius,” which is great.


Joining Metal

Dan Abramson: I’ve been a part of a few site or project launches (I’m very important) and each time, we’ve been hit with the question of “what is this?” or “what will this be?” It’s a fun but overwhelming thought to have right before a launch, calling into question why you’re even doing this in the first place. It’s why the runner Letterman does in the first episode of Late Night resonates so much. After trotting out an old man who would become one of the show’s trademarks and a calvacade of peacock-adorned dancers, Letterman cuts to people on the street telling us what they want to see on a late night show. All the responses are along the lines of “seeing people join metal together.” They then proceed to show boring footage of welders throughout the episode. It told us nothing at all of what this show will be, yet said everything.


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