Letterman and New York

I was babysitting some old neighbor kids in the summer of 2008. That summer I was also going to New York with my family.

One afternoon, probably a week before our New York trip, I took the kids to a free summer concert or show or something at Bridgeport Village, an outdoor shopping center in suburban Portland. I remember my dad calling me to say he’d won tickets to a taping of The Late Show with David Letterman for one night during our New York visit. I freaked out. I had an iPod touch at the time, and remember furiously trying to connect to whatever Wi-Fi network Bridgeport might have in order to research who the guests might be.

I would go with my dad to the taping. I turned 18 a few weeks before so I was just barely old enough to even attend; plus, my mom and sister, Hope, had plans to see some Broadway shows together when we were in town, so my dad and I would do this.

I remember how excited I was at the prospect of seeing Letterman live. The excitement stemmed from multiple sources: The fact that I was just barely making the age cutoff made it seem especially thrilling, like I was really getting to do an adult thing. I loved New York even then, and the idea of going to a Big Cool Event like that in the city seemed incredible. And, there was the guarantee of seeing at least one or two celebrities in person.

And then there was Letterman. I know at 18 I didn’t fully appreciate Letterman’s greatness, but I knew he was a big deal, and I knew he was hilarious. My parents did not religiously watch late-night TV, but they certainly had Letterman on every now and then. Never Leno or anyone else.

Letterman always made me laugh, even when I was little and didn’t get the joke. I knew enough to know I wouldn’t (or shouldn’t) get the joke. I have a very clear memory of being in a hotel room with my parents and sister when I was little, pretending like I was asleep but actually laughing at whatever Letterman was saying on TV. I vaguely remember it being about the 2000 Presidential election, but that could be wrong. Even when I’d watch it with my eyes open, it became the show that I maybe wasn’t supposed to watch, but that I loved being part of.

I may be overstating this, as I didn’t sneak away to watch Letterman every day of my childhood; nor do I have very clear memories of specific guests or segments (besides “Will it Float,” which I loved). But I think that sense of this is for adults but I’m in on it stuck with me and contributed to my excitement about getting to see the show in 2008. It released some pent-up reminder of how subtly influential Letterman had been in my life, up to that point.

The guests that night were Donald Trump and a comedian whose name I do not remember. There may have been a guest between Trump and the comedian, but I do not remember him/her, either. Our show was being taped to air the night of the Beijing Olympics opening ceremonies, so I know there were some broad jokes in the monologue about that. Aleksandr Solzhenitsyn had just died and there was also some gag about inappropriate Solzhenitsyn book titles. I can’t remember the theme of the whole thing, but one of the fake titles was “Slut Beach,” and I’m not really sure why that’s the only specific thing I remember from this episode.

Actually, I remember one other thing: The song playing over the loudspeakers as they loaded the audience. It was Maroon 5’s “Won’t Go Home Without You,” a song which ever since has made me think of New York.

The Letterman taping was something of a seminal moment for me. It made Letterman more real (as I imagine anyone who sees a show or celebrity in person may feel). A year later, Paul McCartney appeared on the show and I loved being able to imagine where I had stood in relation to where Paul stood atop the Ed Sullivan marquee.

Since moving to New York after college, my Letterman appreciation has deepened – partly because my understanding of the TV landscape and Letterman’s place in it is deeper, and partly because it feels pretty cool to turn on the Late Show and know it’s all unfolding 40 blocks away from me rather than from the opposite side of the country.

Superstorm Sandy happened four months after I moved to New York City and while I suffered no personal damage or discomfort from the storm, it hit the city hard, disrupting a routine I was just getting used to. I was alone in my apartment watching Letterman the night he played to an empty audience.

It was a weird end to a weird day at a weird transitional time in my life, but Letterman was a comforting presence. I’ll always associate that show with the storm and my early days in the city.

When Letterman announced last year that he was retiring, I was devastated, primarily because he was the last tie to childhood I had on late night TV. He wouldn’t be around for me to feel cool about watching. It was all changing.

The only major upside to his departure is the natural opportunity it’s created for people to share their best memories and stories of Letterman.

I, for one, had no idea Norm Macdonald had been such a fixture on the show. He re-entered my consciousness thanks to his Twitter poetry after the SNL 40th anniversary special, and his final interview appearance on Letterman not long after was equally brilliant. (He asked Ken Tucker of Yahoo! to live-tweet the appearance and his reflection on the whole endeavor was a great reminder for me of what is unique and necessary about Letterman.)

As far as reflections go, it doesn’t get better than this Times interview, which features too many good Letterman lines to count (“You don’t find yourself filled with some kind of emotional longing? Are we emotionally stable?”).

And while written too early to be a tribute, this short story by David Foster Wallace, recently reposted by Vulture after originally appearing in Playboy in 1988, is my favorite Letterman reflection. I love stories like this that put fantasy characters into reality situations, and this story, imagining an actress’ appearance on Late Night with David Letterman, proves Letterman’s importance and channels his persona (I think the imagined Letterman-Paul Shaffer banter is especially spot-on).

I stayed up to watch tonight’s show, with Bill Murray as Dave’s final guest. It was a typical wild and weird Bill Murray appearance (favorite line, when Letterman asked how he’d been: “I’ve been all kinds of ways. Which ones would you like to hear about?”) but it was also a sad reminder. Only one show left.

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