3 Saturday Night Live Writers on Their Toughest Sketches

Photo: NBC

For a comedy writer, having even one sketch make it to air on Saturday Night Live is a dream come true. On the other hand, trying to get a scene to go from page to screen can be a living nightmare for the staff scribes. As current employee Mike O'Brien and former writers Emily Spivey and Simon Rich reveal, what often seems hilarious on paper can lead to hellish shoots or, thanks to constant rewrites and last-minute hiccups, a disaster that plays out in real time. With the documentary Live From New York coming out today and presenting the show as a rosy place to work, Vulture asked the trio to pick the sketches that gave them the most trouble and lasting agita, and explain how it all went down. 

Emily Spivey, SNL 2001–2010, creator Up All Night, co-executive producer The Last Man on Earth 
Sketch: 2009's "The Today Show With Kathie Lee and Hoda: The Black Eyed Peas and Animals"

I want to preface this by saying sometimes the funniest moments from SNL are the times where the wheels come off. When you're going through it — it's the worst, you just want to die — but looking back on it, seeing the wheels come off is the funniest thing in the world.

The Today show sketch was always a tough one. Whenever you have a situation where you can put different guests in there, it's always changing right up until air. By the time this particular sketch got on the air, the co-writer, Marika Sawyer, and I had been up for probably 36 hours straight. Thinking back on it, that's probably the most time I ever spent on one sketch because it kept being like, "Add this person in, put this in, put that in."

We started out with a pretty solid little sketch: just Kristen Wiig doing her thing as Kathie Lee. In the read-through, the lovemaking ritual of Frank and Kathie Gifford was like four pages long. That was actually what brought the house down: the whole build-up of them making a fine paste and putting it on each other's genitalia. There was also a whole run about them doing it in the gazebo, and it played like gangbusters. But then, people got cold feet because Frank Gifford's a legend and he's getting up there in age. We can't have mean upon mean upon mean, so we had to take some of it out. Right off the bat, it was — I don't want to say doomed, but it had been cut off at the knees a little bit because that had been the focal point of the whole scene.

We also worried about being so mean with Kathie Lee's "Everyone Has a Story" song because we truly love Kathie Lee. We adore her. We had a florist on speed dial to send her flowers after this sketch. She works in the same building, her wardrobe people are the same as our wardrobe people, and they said, "Tread lightly — Kathie Lee takes this song super seriously." But, of course, it got laughs at the table, so we wanted to keep it. Already, our b-holes were really tight about that and what Kathie Lee was going to say. Then we decide that January Jones will play an animal trainer. Poor January, who's already nervous about doing live television, had to be surrounded by reptiles and a live tiger.

So all that was going on and the musical guest was the Black Eyed Peas, and we kept hearing, "Fergie wants to be in something." Finally it came down to us. Because we were so tired, we just said, "Let's have her be so irritated by Kathie Lee that she storms in." And she does this funny bit where she pretends to beat up Kathie Lee. So now we're doubling down on how pissed Kathie Lee is going to be: We're making fun of her song, she's getting beat up, and we're calling her a drunk on television.

After the second rehearsal, we get a call that the rest of the Black Eyed Peas want to see us because they saw the rehearsals and said, "Well, why can't we be in the sketch?" so we were sent in to meet them. We go in there blind, thinking they had an idea of what they wanted to do. We're met with blank, irritated faces. I particularly remember that will.i.am was super irritated and said, "We want to be in this sketch." I said, "Okay, what are your ideas?" and he said, "You're the comedy writer. What are your ideas?" And I, because I had been up for almost 40 hours straight now, said, "Well, you said you wanted to be in the sketch, so we just assumed you had ideas." I'm never that sassy — usually I'm a sweet Southern girl, polite to the end. He went, "Well, that doesn't make sense. That's like me coming into your office and saying, 'Why don't you do a rap right now?'" I panicked and mumbled something about having to go check on the tigers, and Marika and I ran out of the room. So, we handled it perfectly.

I remember saying, "Let's go look at the tiger. We'll figure something out. Maybe the tiger will give us some spiritual guidance." We go in, there's the tiger, and the trainer looks stricken. He says, "This tiger is really scared. I think it's going to be dangerous to put it out there with January. I don't think it's going to work." I said, "What do you mean it's not going to work? She's playing an animal trainer. She has to be surrounded by animals!" So we had to figure out how to write something for Fergie, Will.i.am, the other Black Eyed Peas, and now January? This couldn't happen. That's why, when you watch the sketch, January is standing there with a bunch of empty cages with sheets thrown over them, and the prop guy is backstage shaking the cages like there are animals in there. And beside her on the table is an iguana that looks like it's dead.

It was the first sketch after the monologue. There was so much pressure on it. Scrapping it was never an option. This was the worst-case scenario. Everything that could go wrong went wrong. God love everybody involved. They all just powered through it, but oof. I'm pretty sure Kristen went to lunch with Kathie Lee after that sketch. They had wine together and she had to smooth things over. Even thinking about it now, I'm sweating. It was so scary. After all that work, when I look back on it I laugh so hard, but during that time it was the craziest situation I had ever been in.

Simon Rich, SNL 2008–2011; creator Man Seeking Woman
Sketch: 2008's "Jar Glove"

"Jar Glove" is a parody I wrote during my first few months on the show. I was trying to satirize how infomercials show what life is like without the product they're selling. They always make it seem like it's this hellish experience and it's always black-and-white and melodramatic. I thought it would be fun to take it to its logical, absurdist conclusion. I don't remember pitching it, but I remember handing the script to Seth Meyers to see what he thought. (I don't know how he did it, but every single Tuesday night, in addition to usually writing the best sketches of the week, he would also read hundreds of sketches by all the cast and writers and tell us which ones had legs and then help us improve them. He would often write the best jokes in other people's sketches, uncredited.)

I was coming from the world of print — I had only really written for places like The New Yorker — and I didn't know a thing about film production. I would turn scripts in and only then would it dawn on me that human actors might actually have to endure the pages I'd written, and this is an example. It was a grueling, all-day shoot for Kristen Wiig, and she was an incredible actor, extremely hard-working and willing to do whatever it took to sell the jokes, but I definitely felt guilty when she was stuck inside of that drain pipe. She never complained.

Jimmy Signorelli directed it and I was on the set but contributed literally nothing. (We filmed it at the Douglas House in Rockland County. It's been used for a ton of commercial parodies and sketches, including "Schmitt's Gay.") I mostly just watched from a distance, looking guilty as people did incredibly difficult and sometimes borderline un-producible things to service this crazy idea. One of the many things I regret is the inclusion of dogs, which I remember tripling the work for everybody. In hindsight, some barking sound effects would have done the job, but that's not something that occurred to me.

The great thing about SNL is you get to learn on the job. It can be scary, but I'm so thrilled that Lorne Michaels allowed me to make so many mistakes during those early years. I've never learned so much so fast in all my life. I definitely learned a lot on this endless, hellish shooting day. In general, I learned to never put flying in the sketch, and, whenever possible, try to limit the use of animals. Those are two biggies. Although, for all my talk of dogs, I ended up putting them in numerous other sketches. I always knew it was a bad idea and I always did it anyway. I wrote another commercial parody the next year, a dog-food parody. It was during the recession and it was a bargain brand called "Mostly Garbage," and they brought in more dogs. So, I learned a little bit on the job, but not that much.

It's ironic, given my history of incompetent television producing, that I would try to do such a labor-intensive show as Man Seeking Woman, which is full of monsters and special effects. We wrote a scene in season one where Jay Baruchel goes on a series of first dates and, in every date, he manages to somehow light himself on fire. Luckily, having gone through SNL, I decided at the last minute that maybe we should write something a little more doable with less potential liability. 

Mike O'Brien, SNL 2009–Present
Sketches: 2012's "We're Going to Make Technology Hump" and
2015's "Prom Queen"

I don't know where the idea for "We're Going to Make Technology Hump" came from, but the sketch was very fun to write. I had the most fun writing those little soap-opera scenes, and they were obviously much longer and more involved at the Wednesday table read. By that time, you're trying to get the piece down to three minutes or so for Saturday, so those parts get trimmed down a bit.

One of the cool things about SNL is that they often take these very silly ideas and suddenly you show up at the shoot and there's this amazing production value to it. There were these three miniature sets and big groups of guys huddled around them working on making replica lettuce and tomato that would all be a centimeter big, maybe smaller. The film crew was lighting it so it looked like sunset coming through the windows.

The first one we did, another writer, Shelly Gossman, and I were hand stand-ins for what might have been a 15-hour shoot, just hunched over those tables, trying to get just the right shot of technology humping for hours and hours. We shot all day and night Friday. It was so long and tedious.

With shoots like that, you just see people being broken. I remember a crew guy on the phone with his wife, explaining to her that he wasn't going to be home when he thought he was going to be, and it's because we're having a cell phone hump a nav screen. I'm hearing him saying, "No, I can't. I'm so sorry." I imagine it was their anniversary. "No, I've got to continue making technology hump, so I'm going to miss the anniversary." There's a general understanding that it's their job, but once it's real people doing it, it makes you question the content that you were chuckling at as you were typing it in the middle of Tuesday night.

That one wasn't too demanding on the host, but "Prom Queen" with Michael Keaton from this past season was. So, in that way, I hadn't learned the lesson. It was something we talked about but we were like, "I don't know how to make it have less Keaton. He's the lead and needs to be in basically every scene." With someone like him, I didn't just want to make him one of the extra teachers. That's no fun. You want to see Keaton as the lead, but we did need him to shoot from midnight until question mark on Friday night, knowing he's going to go home, get a small amount of sleep and come back for a 14-hour day that ends in a live show. You're like, "We gotta get him outta here!" but you're balancing that with "We've got to get all the shots so we have a narrative to piece together." On Tuesdays, that's a constant debate: "This video would be better if we had the host in it and we could film it at 50 locations, but since we're going to have to shoot this all in one day and we don't want to break the crew, the host, and everyone's spirits for life, what's a way we can trim this down?" You end up having everything happen in one location. On Wednesday, the bosses said, "Go sell Keaton on 'Prom Queen,' or describe it to him, make it so he's enthused about it because we're going to have to keep him up in the middle of the night before he hosts." He was receptive to it right away and then I emailed him the script that night and he immediately had thoughts and ideas of what could be good, so luckily he was that type of host.

There are some times where the host is a little confused by the tone of it, like J.K. Simmons was all for being in "The Jay Z Story," but he was obviously very curious. He said, "I don't really know who Nas is or how he talks," and I was saying, "You don't have to." And he's like, "But I'm Nas?" and I'm like, "Yeah, I know it's a little weird, but once you see it it'll make sense." He hadn't heard that one at the table read so he was like, "How are you doing your Jay Z? Is there any blackface in this video?" I said, "No, of course not. Jay Pharaoh will do an impression of Jay Z at one point but otherwise, no one is trying to nail impressions of these people. In fact, the opposite. Just be yourself." He said, "Okay, then why? What is it? What the hell is this thing?" And then he got it.

It's just so hard when you get into writing something. The whole idea of what's exciting to us about this profession is you think, What if anything could happen now? and anything you think of, you can type. It's hard to say, "Let's just make this a quick exchange in a normal-looking office." You've got to be like, "A dragon could walk through. Let's do it!"