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Interning back in the day: December 1998

In case you haven’t been following the shifting landscape of late night television, tonight marks the last episode of Late Night with Conan O’Brien. The good news is that Conan will be moving up to the Tonight Show later this year, and technically, Late Night as a show will motor on — except now with host Jimmy Fallon behind the desk. Many people suspect that with the move to the earlier time slot, some of Conan’s trademark humor (Masturbating Bear, etc) might wind up cut from his show. I don’t know if this is true or not, but I think it is safe to say that there will probably be a slightly different flavor to the proceedings, which isn’t necessarily a bad thing, but it does mark the end of a late night era. It’s an era, I’m proud to say, that I participated in for a few months ten years ago.
Back in the summer of ’98 (and again in December of that year) I served as an intern on Late Night with Conan O’Brien, and the experience, to sum it up in one word, was amazing. To this day, it pretty much remains the most amazing job I’ve ever had. Sure, I’ve had great work experiences, but nothing can compare to the excitement, the insanity, and the general sensory overload of working on a show like Late Night and in a place like 30 Rock.


Back in ’98, I had just finished freshman year of college, and the internship was sort of like my first real job. I had never worked in New York City before, let alone on a television show. My first day was kind of like a blur. I got lost in the building no less than about ten times, and I remember walking out on the stage and being more or less awestruck to actually be standing by Conan’s desk (he wasn’t sitting there. It was about 9 AM). I didn’t have much time to let it sink in though because soon I was off on my first run to fetch something or another in the city. A fellow intern, Tim, had to join me since I was a newbie to the subway system, and I remember we talked about wanting to be writers. Back then we thought we were being realistic by not attempting to write for The Simpsons or Friends but instead opting for the low-hanging fruit of the WB and the UPN, the assumption being that jobs on those shows would be readily available to any aspiring writers. Ah, to be young.
Yes, that first day of work I learned many lessons: not the least of which was that I was an intern and not very important. When it came to the executive producer of the show, we were told not to make eye contact, not to talk, and not to even bother smiling. Invisibility was the key. Also, every day, we had to fetch him a double-tall skinny latte — an order that has become permanently etched into my brain. Needless to say, there was nothing worse than a) getting stuck in an elevator with the guy or b) heading down a hallway and seeing him coming from the opposite direction. You always felt that he might just turn to you and say, “You looked at me. You’re fired.”
One time, I was actually in Andy Richter’s office, and we were bantering about something or another, and somehow I wound up saying something like “And here’s a dildo!” I don’t remember the context, but I specifically recall the word “dildo” being uttered by me. Suddenly, I heard a voice behind me: “Excuse me?” I turned around, and there was the executive producer standing right there. Embarrassed and frightened were just two of the intensely unsettling emotions I felt at that moment. I was actually shocked when he simply laughed and said “Who’s talking about dildos?” We all laughed, and then I conveniently DISAPPEARED. I learned then that maybe the guy wasn’t so much a terror — just too busy for interns. (But seriously, if someone says hi to you, you can say hi back.)
Of course, one element I loved about the show was seeing all the celebrities waltzing through day in and day out. On my first day, I handed a cup of coffee to Laura Linney and then awkwardly informed her that she was quite good in The Truman Show. She was very sweet and thanked me with a big smile. I’m sure she still remembers the moment well.
Other celebrities weren’t as friendly. I remember Rufus Wainwright being an absolute terror. And then there was this one band that made me march all over Manhattan to fetch them a specific type of donut. I really wish I could remember more celebrity stories, but they unfortunately all blur together at this point. Granted, being in 30 Rock, there were some generally odd things that happened. One time, the elevator doors opened up and Katie Couric came running out in a sports bra. It only took her about two seconds before she realized she was not at the company gym as she had previously expected. One second later, she was back in the elevator and gone. It was quite surreal.
Surreal, however, was kind of the name of the game at Late Night. I remember one time being backstage just prior to show time and standing between Emmylou Harris and a sloth. Another time, I was told to dress up as a bear (not the masturbating one) and attack Conan. Unfortunately, the producers dropped the bit before I could display my ursine acting abilities, but it was still quite the bizarre situation to be in. Then there was the time I went into the prop closet and came face to face with Triumph the Insult Comic Dog. The puppet was just sitting there, lifeless. It was weird. And awesome.
One of the best parts about being an intern was going on “remotes,” which was essentially a shoot that took place outside of 30 Rock. You’d get to spend all day near the heart of the action — plus, the locations were cool. There was the time we headed out to a beach in the Hamptons (where I accidentally walked in on Max Weinberg wearing a speedo in his dressing room). And there was the time we stayed up all night on a pier as we taped Conan jumping into the East River (a bit that was used for years in the opening credits). The best remote of all, however, was the aforementioned bear remote. We all traveled up to a park in Nyack, and I had the good fortune of being in the same van as Conan, Andy, and several of the writers. Up to that point, I’d had considerable interaction with Andy and the writers (all of whom were super nice and friendly and treated the interns wonderfully). I hadn’t, however, said much to Conan. It’s not that he was standoffish — he was just busy. He was either in his office or down in rehearsals or working out or doing whatever. It was rare that our paths ever crossed.
On this occasion, however, we were stuck in the same van for an hour and change. I was very excited. On the trip up, I was mostly silent. I followed the age-old rule: be seen but not heard. It would have been out of place for me to start gabbing away with the writers. When we reached our destination, however, I somehow got left in the van alone with Conan. This was my chance. I could finally talk to him. And what did I do? Well, I acted very awkward. I remember asking him about Harvard — I think maybe something about when he graduated. He told me when, and then there was some very forced and forgettable light conversation afterwards. It was pretty much awful. I was acting awkward (surprise), and he clearly wasn’t in the mood to chit chat. Thankfully, we were told to get out of the van about two minutes later, and the uncomfortable moment could finally draw to a close.
We then spent the next seven or eight hours in the park shooting various things. I don’t, for the life of me, remember what we did. I’m still trying to remember if I even got into the bear costume. I think I did. Whatever it was, at the end of the day, everyone was tired and done and ready to go home. We all got back in our vans, but this time, the vibe in my van was completely different. Everyone was just so happy to be done with work for the day that we all started chatting. Intern, writer, star — it didn’t matter what you were. It was banter-riffic. And I couldn’t help thinking in the middle of it “Oh my God. I’m bantering with Conan O’Brien!” (I didn’t say “I’m bantering with Andy Richter!” because I’d already had that moment earlier in the summer). Conan, meanwhile, slipped into host mode, and for a while, I felt like a guest on his show. He kept asking me questions about my life, and pretty much anything I said he’d turn into a comic riff, which Andy would then jump in on. As an intern, it was sort of like the best exposure to these guys you could ever ask for.
Of course, watching Conan’s comic genius at work was one of the highlights of the job. Every day, we’d get to watch him in rehearsal, and for me as an aspiring writer, I felt I really learned a ton just by observing his choices and process in those afternoon sessions. Later on in my tenure there, I got to temporarily be a script intern, which meant I spent all day distributing the script all around the building. It was a stressful position (made more so by the fact that my supervisor, a woman named Andrea Kail, pretty much hated me. I mean, she despised me from the very first moment I came on board with her. Why, Andrea? WHY?), but on the upside, script interns got fantastic exposure to the writing process. We’d have to sit there backstage, just minutes before the show, and watch as Conan read through the monologue jokes for approval. Even better, we’d also get to sit in the control room and watch the show tape from there, which was nothing short of an overwhelming rush. I’m shocked my head didn’t explode at any point during that summer.
There really was so much to take in, and putting on a show four nights a week meant that as an intern, we could see the direct results of our work. Yeah, sometimes we’d have to fetch something crazy from across town, but that night, you’d see it on the show and could say “I fetched that!” Hey, when you’re working for free, you’ll take whatever value you can. Being able to see the fruits of your labor really was an important motivator as an intern. I later worked as an intern on Strangers with Candy, which was also a fun process, but obviously the turnaround for shows would be weeks or months. As a result, we interns kind of worked in a void. We just picked stuff up and did errands, but we never really saw what our work was contributing to until much later. There wasn’t that same rewarding feeling as watching an entire show come together in just a few hours’ time. Of course, there were other benefits to that experience, but I won’t get into that now.
I honestly could go on and on and about my internship experience, but I fear I’ll just be like one of those old men who tells stories of yore and never shuts up. The point is that much of my success in my current career can be traced back in some way or another to my time on Late Night with Conan O’Brien. I really hope for nothing but the best for Conan and his crew on the new show, and I’m incredibly thankful for the experience and memories. Oh, and I also had an awesome boss, Ron Motta, who’s on Facebook and will probably read this. So… hi Ron.