'SNL' Political Secrets Revealed: Hillary's "Entitlement," the Sketch Obama Killed and the Show's "Karl Rove"

This story first appeared in the Aug. 29 issue of The Hollywood Reporter magazine.

From Chevy Chase's bumbling commander in chief to Tina Fey's dim-witted veep wannabe, political satire always has been a part of Saturday Night Live. And over its 39 seasons, actual politicians have clamored to be in on the joke. President Ford, running for a second term against a peanut farmer named Jimmy Carter, appeared on the show's very first season, in April 1976, to deliver the cold open ("Live from New York, it's Saturday night!"). Since then, presidents, first ladies and candidates of all stripes have made campaign stops at Studio 8H.

For a time, after 9/11, the cast and writers gave politics a rest. As Amy Poehler recalls, "The news was so bad [we] could barely do anything political." But political humor made a roaring comeback with the 2008 election. That political cycle's most bizarre media meta-moment had to have been Sarah Palin appearing on SNL on Oct. 18, 2008, alongside Fey impersonating Palin (the segment helped the show draw its largest audience in 14 years with 14 million viewers).

A new edition of the classic Saturday Night Live oral history, Live From New York, by James Andrew Miller and his co-author, Pulitzer Prize-winning Washington Post television critic Tom Shales (on sale Sept. 9), adds 200 pages of new material to the original 2002 book, updating the story through the 2000s. THR's exclusive excerpt reveals some of the behind-the-scenes battles and backstage shenanigans that shaped the political landscape of the past decade — including how presidential candidate Hillary Clinton made a last-minute decision in 2007 to cancel her SNL appearance, opening the door for a certain senator from Illinois to take her place — and even influenced the outcome of presidential campaigns.
— Andy Lewis

I. The 2008 election

Lorne Michaels, executive producer: We were contacted by, I think, Howard Wolfson from Hillary [Clinton's] campaign, and they wanted to do the first show of the season. [Barack] Obama was heating up, but they called first, so I said OK. You have to play by those rules. And then, the week of, they bailed. I went, "Really? You called us, and we gave it to you." I think every now and then I get carried away and think we actually do have influence. And then, after that, we put Obama on the date when Hillary was supposed to be on. The sense of entitlement which was following her everywhere at that point peaked for me at the bailing.

Tina Fey, castmember: It was August of 2008, and I was on Fire Island with my husband, Jeff, and it was funny because he had the cover of the Times that said, "McCain Picks Running Mate," and he said he thought there was a resemblance. I said: "I don't think so. It's just brown hair and glasses." But when we got back to the city, some cousins and old classmates were all saying, "That lady looks like you." I was sort of — arrogantly, in my own mind — resisting it, like, "I don't want to play that, and I don't know who's gonna write it, and what if I don't like what they wrote, people are going to think that I wrote it." And at some point, I realized that, like, "Oh, by the way, no one at SNL has actually asked me to do this."

Michaels: Right after the [vice presidential] debate [in October 2008], I'm coming out of my building the next day, and my doorman, Frank, says: "Mr. Michaels, what a gift! Did you see it last night? It's Tina Fey!" And I go, "No, Frank, she's not on the show anymore." And I'm literally 30 feet away from my apartment, and Bobby De Niro's there with his daughter, and he goes, "What a gift." I called Tina and said, "I think the audience is demanding that you do it."

Seth Meyers, head writer-castmember: The "Russia from the house" line? That was not [in the] first draft. I believe I'm going to give credit to [writer] Mike Shoemaker for that line. That was the thing about those sketches — you were constantly carrying them around and reading through them for whoever you could get to listen, and people would just constantly pitch jokes.

Michaels: You could see perception changing completely. It's [Jon] Lovitz as [Michael] Dukakis going, "I can't believe I'm losing to this guy." Or Chevy [Chase] as Gerald Ford going, "I was told there would be no math." The audience that was suddenly watching Sarah Palin wasn't necessarily the SNL audience. Tina crossed over. It made her a huge star.

Sarah Palin, guest: I think SNL is egotistical if they believe that it was truly an effect on maybe the public debate about who should lead the country in the next four years.

Amy Poehler, castmember: Playing Hillary and Sarah Palin was an indication of women taking center stage in politics in a way that I hadn't been able to experience in my time there. My first show was two weeks after 9/11 happened, and for the first three or four years of my time there, we could barely do anything political. Everyone and everything was so tender, and we had lost Will Ferrell as our [George W.] Bush. Everything was so bad; the news was so bad. There was a lot of pop-culture stuff, and getting to finally do really deep political parody at the end of my career there felt really satisfying.

Michaels: I called Alec [Baldwin] to come in for [Palin's appearance on Oct. 18, 2008], to be standing with me, because he was the most emblematic liberal at that point. He said he had to introduce a documentary at the Hamptons Film Festival on that Saturday, so he wouldn't be able to do it. So I said, "Alec, your instincts are always great, but are you telling me you're not going to be here for this thing that the whole world is waiting to see?"

Fey: I was the one pitching, "Why don't you start her backstage, you know, with Alec, so the crowd won't boo." She had just been booed at a hockey game in Philadelphia, and I thought we had to be cautious. And of course the audience was just happy to see her because she was a star, a media star. Even the New York audience was not feeling their politics at that moment.

Michaels: Tina was terrified of anything where they would be together looking like an endorsement.

Palin: I know that they portrayed me as an idiot, and I hated that, and I wanted to come on the show and counter some of that.

Michaels: [Palin] has wonderful manners — and I honestly don't mean this in a condescending way — but it's that pageant-winner thing.

Palin: If I ran into Tina Fey again today, I would say: "You need to at least pay for my kids' braces or something from all the money that you made off of pretending that you're me! My goodness, you capitalized on that! Can't you contribute a little bit? Jeez!"

II. The impersonations

Bill Hader, castmember: I remember Seth Meyers very clearly coming up to me and saying: "[Writer-producer James] Downey just wrote a cold open where you play Eliot Spitzer. Do you have an Eliot Spitzer?" And I said, "Who's Eliot Spitzer?" And Seth is like: "You're an idiot. One, he was our governor." I know nothing. So it was like, "Go watch this tape, watch him give this speech and figure this out, you dummy." And then I would figure it out, and I learned I was a pretty quick study at this stuff.

Horatio Sanz, castmember: I always kind of felt bad when Will Ferrell did his Bush impression because he was such a good old boy that you really didn't think, "Oh, this evil little rich prick whose dad and his friends got him in office." You thought, "Oh, he's just a good old guy I'd like to drink beer with." As funny as Will's impression was, the audience as a whole, the whole country, would probably see that as, "Oh, I like Bush. Because he's Will." You know, if Will hadn't done that impression, or at least made him likable, it may have tipped it the other way. I honestly think so. We made up for it. I think Tina's impression basically killed Sarah Palin.

Will Forte, castmember: I did not want to do Bush. I'm not an impersonator. Those presidential election periods and those great debates that I'd seen over the years were a really special thing about the show, but I felt like I was part of the one period that might not have been so great just because I didn't think that I was that good. It's a shame because Seth Meyers did a great John Kerry; he would hold up his end of the deal, but I just didn't give him anything great to play off of. It was also hard because Will Ferrell was so good at it. It was almost like somebody coming in and taking over the role of Church Lady. That's Dana Carvey; nobody else can do Church Lady. And that's kind of what it felt like with George Bush. You can't retire George Bush because somebody's gotta be him.

Will Ferrell, castmember: I get asked in a press junket, "Do you have a good Obama up your sleeve?" and I'm like, "No." Once I left the show, I stopped trying to think of political impressions. But also, Obama is difficult. He's very dry and subtle. And yet you see Jay [Pharoah], and the people get it down, and you're like, "Oh, there's the impression."

James Downey, producer-writer: If I had to describe Obama as a comedy project, I would say, "Degree of difficulty, 10 point 10." It's like being a rock climber looking up at a thousand-foot-high face of solid obsidian, polished and oiled. There's not a single thing to grab onto — certainly not a flaw or hook that you can caricature. [Al] Gore had these "handles," so did Bush, and Sarah Palin, and even Hillary had them. But with Obama, it was the phenomenon — less about him and more about the effect he had on other people and the way he changed their behavior. So that's the way I wrote him.

Fred Armisen, castmember: My approach to everything in life is, "Sure, I'll give it a try." I knew they were looking for an Obama, so when Lorne called me into his office and [producer] Marci Klein said, "Let Fred do it," and Lorne was like, "Would you want to try it?," I was just like, "OK, I'll give it a try." They asked me on a Tuesday, and I think I did it that Saturday. I bought Obama's book on iTunes, and I watched videos.

Jay Pharoah, castmember: I did an event at Harvey Weinstein's house — very nice; I'd never been there. I was trying to take my makeup off because I was [Obama] at this event, and [Obama] stood right there watching me do it. He was laughing; it was so petrifying. As long as there's no beef between me and the president, that's good. When that happens, you're Kanye West.

Paula Pell, writer: I planned that I was going to come up and talk to [Palin] and shake her hand and welcome her and say, "My wife and I are very good people, and we live a very socially conscious life, and we do a lot for our community, and I just want you to know the face of gay couples and gay people," and I had this whole speech planned. Then I just kind of came up to her in the chaos in the hallway and just nodded and said "hi" and walked off. I thought to myself, "I'm such a chickenshit." I was like, "Wow, she's pretty." I just got overwhelmed by the fact that this character who was everywhere on TV was in front of me, and she was real and just ridiculous. So I didn't get my big political moment.

III. The (office) politics

Downey: The biggest risk to doing political comedy is, you always seem to have a choice: Am I going to piss off the audience by trying to get them to laugh when they don't like what I'm saying, or am I going to kiss their ass and get this tremendous wind at my back by sucking up to them? The second way makes me feel like I cheated. I'm sure there are a lot of people in comedy who completely share every f—ing detail, jot and tittle of the Obama administration agenda, and all I can say is: To the extent that you're sincere and that's really the way you feel, then you're a very lucky person because, guess what, you're going to have a very easy career in comedy because audiences will always applaud. They may not laugh, but they'll always give you [a] huge ovation. That's Bill Maher, you know?

Robert Smigel, writer: It wasn't until my last season that the network refused to air a "TV Funhouse." It was a live-action one that was meant to be about racism and profiling, an airline-safety video with multilingual narration, and whenever you heard a different language, they would cut to people of that nationality. First, typical white Americans, then a Latino family, then a Japanese family, all being instructed about seat belts, overhead compartments, et cetera. Then it cuts to an Arab man, and the narrator says, in Arabic, "During the flight, please do not blow up the airplane. The United States is actually a humanitarian nation that is rooted in the concept of freedom," and so on. … When the standards people freaked, Lorne fought them. Standards pushed back hard. They even got someone at NBC human resources to condemn it. … Lorne said, "I have a plan." Obama was doing a cameo in the cold open. Lorne told me he would show my sketch to Obama. "If Obama thinks it's OK, they won't be able to argue it." I thought it was a brilliant idea, except why would Obama ever give this thing his blessing? What if word got out? "Hey, everybody, that guy over there said it was cool. The one running for president of the country." But I loved Lorne for caring this much and being willing to go that far to get this thing on TV.

Michaels: Obama said, "It's funny, but no, I don't think so."

Downey: There was one Bush piece I did a couple times in dress that I think died twice and was never on. It was after Abu Ghraib. I knew I was in very dangerous comedy territory, and it was a piece where Bush was trying to justify Abu Ghraib. He was addressing the nation and saying it was an attempt, maybe awkward on our part, to make Iraqis more comfortable with their bodies. There was something about the joy of the nudist lifestyle, and I remember at one point it had a joke like, "Many people have objected to the fact that the detainees were forced to mime sex acts. Now, is it the fact that it was sex acts that you find offensive or is it that it was homosexual sex acts? Think about that, then tell me who's in the wrong here." I thought it was funny. It was a desperate attempt to turn the tables on critics. When we did the sketch [in dress rehearsal], it was like a death camp in there; the audience was like, "No." There's not laughing, and then there's aggressive silence.

Sanz: I don't think the show itself has ever let its freak flag fly in the last 20 years. Lorne's very concerned with being neutral so he wants to make fun of everyone. … He doesn't want the show to be this liberal bash rag. He may be a little more conservative than he lets on. … And you also have Jim Downey, who's basically the Karl Rove of SNL. He's always writing the right wing sketches, and honestly I think a lot of times they're out of tune with the audience. … I think Lorne sometimes leans too much on Downey and not enough on guys like Seth. Basically in the last couple of years, it's been Seth going up against Downey to set the show's tone on politics, and I think we could definitely have been harder on the right. They deserved it, and we dropped the ball as far as getting them.

Downey: My mission is to try to write a funny piece using politics as the subject matter, and so I go with what I think is the most interesting, potentially funny idea that no one else is talking about.

Sanz: The week that Nancy Pelosi was made speaker, the only thing that we could come up with at the time was, because she was from San Francisco, to make her a dominatrix. I thought that was really, really cheap. … It was pretty frustrating. And it continues to be frustrating. I don't really like watching the political scenes that much anymore because they're not written in the writers' and actors' tone. They're written like Downey wants to put this message out. And I think that's kind of shitty.

Downey: I used to write this stuff with Al Franken when we started out; I was a standard-issue Harvard graduate commie, and Al was like a Democratic Party stalwart. I had contempt for the partisan stuff. And I became more conservative over the years, to the point where I'm now a conservative Democrat, which means in Hollywood terms I'm a McCarthyite, I suppose. But I have to say, and even Franken agrees with me — I've talked to him about this — that the last couple seasons of the show were the only two in the show's history where we were totally like every other comedy show: basically, an arm of the Hollywood Democratic establishment. [Jon] Stewart was more nuanced. We just stopped doing anything which could even be misinterpreted as a criticism of Obama.

Smigel: My last cartoon, in February 2008, was "The Obama Files" — about candidate Obama's efforts to distance himself from Jesse Jackson and Al Sharpton without alienating them. It turned out that on the same show, Hillary Clinton made a cameo in the cold open. She was planning to leave right after, but Lorne liked the cartoon and asked her to hang around for 20 more minutes and watch it. She was laughing a lot at the cartoon. Then about halfway in, I remembered that the ending might not be as much fun. It had Sharpton and Jackson falling through a trapdoor and landing in a "community van" with other political liabilities, including Bill Clinton, who then asks the driver to head for spring break. Relatively tame, but still it's her husband. Fortunately, Poehler walked in just before then. Hillary still saw it and chuckled politely, but her focus was split and awkwardness was averted. Later, I saw Lorne, and the first thing out of his mouth was, "I forgot about the Bill part." I assure you, the fact that it was my last cartoon is a total coincidence.

LIVE FROM NEW YORK Copyright © 2002 by Thomas W. Shales and Jimmy the Writer, Inc. Excerpted material copyright © 2014 by Jimmy the Writer, Inc.