Bossypants (20 page)

So You Can Imagine My Surprise…

So you can imagine my surprise on August 29, 2008, when my husband called me into the room to watch CNN. John McCain had selected first-term Alaska governor Sarah Palin as his running mate, and two things were obvious right away. One, this was a craven attempt to lure Hillary voters away from Obama, and two—“She kind of looks like you,” my husband said. I scoffed. It was just that she had brown hair and glasses. But the e-mails started coming, from friends and cousins and coworkers. People seemed to think we really looked alike. The most powerful minds in the world—cable news anchors and Internet users—started speculating as to whether I would play her on
Saturday Night Live.

We had already done two full seasons of
30 Rock
and were just beginning to shoot season 3. If I had been wondering whether people were aware of the new show, the answer was now clear;
they
were not
. No one had even noticed that I didn’t work at
Saturday Night
anymore. Also, no one seemed to remember that when I
did
work there, I only did the news. They didn’t care. They were in a blind frenzy. “Brown hair! Glasses!”

In a Shocking Turn of Events…

In a shocking turn of events, Oprah Winfrey had expressed the slightest polite interest in being on
30 Rock
. Desperate to find a larger audience, we jumped at this chance like meth heads over a cough syrup counter. Robert Carlock wrote a hilarious script where Liz Lemon meets Oprah on a plane. (You can buy it on iTunes!) We sent the script to some women at Harpo, who told us that Oprah liked it and they were sure she would do it. We were ecstatic. As the summer wore on, however, it became clear that Oprah had not actually seen the script. In late August, Oprah’s chief of staff (I am not joking) had called to say that Oprah was really sorry but she would not be able to do the show. This was planned as our second episode of the season, and Oprah was irreplaceable in it. We had already shot half the episode. If this fell apart now, it would cost the show hundreds of thousands of dollars. I had the nerve-racking task of getting on the phone with Ms. Winfrey and trying to talk her into it. I am terribly, terribly suited for such jobs. I’m shy and have no salesmanship—I am actually able to convey sweaty palms over the phone. I didn’t try to sell Ms. Winfrey on the comedy of the episode; instead I appealed to her knowledge of television schedules and how royally cornholed we’d be if she declined. She listened, because she is smart and generous. She agreed to let us do a rewrite of the script and consider it, but I knew that until that Oprah footage was “in the can,” I would carry around a very specific form of physical anxiety that feels kind of like my heart shrinking up like a raisin.

Meanwhile, Across Town…

Meanwhile, across town, the staff of
Saturday Night Live
was preparing to start their season early, on September 13, to cover this very important national election. The show is always exciting during election years and has proven its political relevance time and time again over its thirty-five-year run. (I have to include sentences like that because I’m trying to get college credit for this.) On September 3, 2008, then governor Palin accepted the vice presidential nomination. Around this same time, Oprah formally agreed to be on
30 Rock,
and it was determined that my daughter’s third-birthday party would have a Peter Pan theme. Each of these events was equally important in my life.

Lorne and I discussed the overwhelming public opinion (hyperbole) that I should play Governor Palin. Apparently, that morning both Lorne’s doorman and Robert De Niro had stopped him to say how uncanny the resemblance was. Did we dare disappoint Frank the Doorman and Robert De Niro?

Lorne and I shared the same hesitation: If everyone in the world had the same casting idea, it couldn’t possibly be a
good
idea, right? When you work at
SNL,
people come up to you all the time and say stuff like “You know what you should do? A skit about my brother-in-law,” or “You should do a skit where Tiger Woods and Obama are gay for each other.” Or “That show hasn’t been good since the seventies.” People always have lots of opinions about the show and they’re never right, so why would they be right now?

But Lorne is also an old-school producer, and somewhere deep down I think he knew that if he cast me in the part “by popular demand,” even if I sucked, it might be a good rating. A good rating is a good rating, even if people tune in just to be mad about how much it sucked.

We decided not to decide. This is another technique I’d learned from Lorne. Sometimes if you have a difficult decision to make, just stall until the answer presents itself.

Back at
30 Rock…

Back at
30 Rock
we scheduled our shooting day with Miss Oprah Winfrey. She generously offered to fly in on Saturday, September 13, to pick up her scenes. This was perfect. I could safely plan my daughter’s party for Sunday the 14th. The only remaining problem was that I could not find Peter Pan plates or cups. You can find Tinkerbell or Captain Hook, but no Peter Pan. Was Disney in some kind of legal conflict with the J. M. Barrie estate? There was no time to get involved in that! I had less than a week! Captain Hook cups mixed with Tinkerbell plates would have to suffice.

It was four days until the season premiere of
SNL
and still no decision from Lorne. I was walking around the
30 Rock
offices telling everyone that I couldn’t possibly play Palin—I was too busy and I didn’t do impressions and it’s important to say no sometimes and I couldn’t possibly commit to it—but in the back of my head, I was very aware that no one had actually asked me to do it. “Has he called you yet? Has he called you yet?” my friends were asking. Nope. I slumped against my locker and twirled my ponytail.

I had arrogantly thought it was all about me and whether I felt like doing it, but of course it was
Lorne’s
decision to make and not mine. It’s
his
show.

Still trying to control the situation, I called Lorne’s office on Wednesday evening after their read-through and left a message to say I didn’t want to play Palin, should it come up. My call was not returned.

On Wednesday night, Alice and I drew a picture of Peter Pan to hang up at the party. I explained to her the apparent licensing problem with the plates. She was understanding and suggested we relax by pretending to be Wendy and a mermaid for the next sixty-five minutes.

On Thursday, Oprah’s office checked in to say that she had heard I might be doing
Saturday
Night Live
that Saturday and would I rather reschedule her shoot? No, no, no! Get the “O” in the can, for the sake of my heart raisin.

Thursday morning I checked the status of my Amazon.com order. The birthday present I had ordered was not here yet. I also started peeking at YouTube clips of Sarah Palin. How hard could that voice be?

On Thursday evening, Lorne called to say that Seth Meyers had written a piece and I should come over late Friday evening and rehearse it with Amy and if it didn’t feel right, someone else would do it.

I rambled through my concerns. Kristen Wiig would be better at it. (Lorne agreed.) I felt that whatever I appeared in, people would assume that I wrote it and that it was expressing my personal opinions. These were delusions of grandeur, of course; remember, no one even noticed that I had quit.

Regardless, I didn’t want to be a stock character that any writer on the staff could make use of. I didn’t want, for example, to play Sarah Palin in a sketch about how Hillary Clinton was a jealous dyke or something.

Also, I was skittish to do political comedy after getting myself into trouble a few months before.

My Mouth Goes into Politics. The Rest of Me Is Forced to Follow.

After the Writers’ Guild of America Strike that Changed the World in 2008, I was asked to host
the first Saturday Night Live back on the air. Finally, the world would see my full range of comedy
characters—from grouchy librarian to Russian librarian.

Seth and Amy asked if I wanted to come on Weekend Update to do a “Woman News” segment.

The piece the Update writers and I threw together was meant to be about the way Hillary Clinton was
being treated and perceived during the campaign. It was meant to point out that America seemed more
comfortable with a male minority candidate than a white female candidate. It was meant to discuss (in
joke form) that people didn’t take to Hillary because of this vague feeling that she was kind of a bitch
and how unfair that was. It was meant to be about gender politics, not actual politics.

What came out was an overt Hillary Clinton endorsement.

It wasn’t that I didn’t like Mrs. Clinton as a candidate; it’s just that Weekend Update features are
written so hastily. If you’re hosting, you don’t even start writing them until Saturday afternoon. It’s no
surprise that they can come out sloppy and strident. I was in the host’s dressing room between dress
rehearsal and air—feeling like Stallone, but without the cigar or the nice teeth. I just wanted the show to
be good. I needed a punchier ending to the Hillary Clinton Update piece, and my friend and makeup artist
Richard Dean suggested “Bitch is the new black.” It made sense in the context of the piece and was
certainly punchy. Also, it was about 11:10 P.M., so yeah, let’s go with that.

I would have chosen to stop short of being overtly political if I’d had more time to smooth it out,
because one: I think it’s more powerful for comedians and news anchors to be impartial, and two: I am a
coward.

The next day Obama supporters on the Huffington Post were outraged. Former president Clinton
called me at home to thank me. Mrs. Clinton called later that same day to thank me, proving that Bill is
just a tiny bit better at the flash-charm-handshake part of politics.

When I told my mom that former president Clinton told me I “did a great thing for my country” in
defending Mrs. Clinton like that, she made a barfing sound. Did I mention that my parents are
Republicans?

Friday came, and I know what you’re wondering—yes, the Imaginext pirate ship and sea monster I had ordered did arrive, and I wrapped them in my dressing room between setups. I shot for twelve hours at the fake 30 Rock, then, after inspecting the cleanliness of Oprah’s airplane set and dressing room for the next morning,* I headed over to the real 30 Rock at about ten P.M. to rehearse with Amy Poehler. I took comfort knowing that Amy could carry the sketch if I stunk it up, because she’s such a skilled and generous performer. I mean, she’s no Kattan in a dress, but considering the Darwinian limitations on women in comedy, she does very well for herself.

We went out on the studio floor in front of the crew, and I tentatively tried out my half-baked impression. Not the worst. Significant room for improvement.

Because Seth and I had written for real impressionists like Darrell Hammond over the years, we knew there were certain tricks we could employ. Whatever sounds are helpful to the impression, you use as many of them as possible in the writing. For Palin it was a lot of “hard R’s.” Words like “reporters and commentators.” Words you can’t say, you avoid. For example, I’ve never been able to figure out how she says “Todd.” Amy added jokes. I added some jokes. The whole process was pleasant and collaborative and easy.

Saturday, September 13, I got up at six A.M. and filmed my scenes with Oprah at Silvercup Studios in Queens. She was great. She really does smell nice. And I got to hug her a lot in the scenes. (If you’re not into iTunes, you can buy
30 Rock
on DVD at your local Walmart.) Between setups I sat with my daughter on my lap and watched Governor Palin on YouTube and tried to improve my accent. Oprah seemed genuinely concerned for me. “How much rehearsal time are you going to get?” “Do you have tapes of her to listen to?” “You’re going there right after this?!” (By the way, when Oprah Winfrey is suggesting you may have overextended yourself, you need to examine your fucking life.) Around 5:30

P.M., Oprah and I wrapped and I went over to
SNL,
but not before stealing an untouched Edible Arrangements® bouquet from Oprah’s dressing room to serve at the birthday party the next day.

The rest of the night went thusly: I got to
SNL,
I tried on my wig and outfit, Amy and I did the sketch three times—run-through, dress rehearsal, and live—and that was it. By 11:40 P.M., I had the rest of the show to relax and have a glass of wine. It was actually the first night out my husband and I had in months.

The whole experience was surprisingly serene. Maybe it was because the Oprah footage was “in the can” and my heart could stop eating itself. Maybe it was because I was safe at the side of my sweet friend Amy. Maybe it was because I knew I couldn’t get fired because I didn’t even work there anymore anyway. Obviously a big part of it was that Seth had written a very good sketch. I was not nervous at all, and doing that sketch on live TV was a pure joy I had never before experienced as a performer.