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Mike O’Brien on His Jay Z and Oprah Sketches and SNL’s History of Undercutting Premises

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From Baby Boss to Roseanne Roseannadanna, Saturday Night Live is known for repeating characters, so when it happens, fans are rarely surprised. That was not the case in April of this year, when SNL writer-actor Mike O’Brien repeated the character of terrible biopic star Mike O’Brien, who played Jay Z when we first saw him in January 2015. O’Brien felt his brilliant, fake Jay Z biopic needed a sequel, and when it came time to pick a subject, the choice was clear: Oprah! Now that the SNL season is over, O’Brien talked to Vulture about shooting Oprah, failing to get Whoopi Goldberg, and the sketch trick of undercutting the premise towards the end.

I want to talk about the Oprah sketch, but I feel like to start there, we have to go back to the Jay Z sketch, as they’re parts of a whole. Can you tell me about the journey of getting the Jay Z sketch on air?
The first time I heard Jay Z, I was 12 … we won’t go back that far. But it was a long process, with it getting kicked around for weeks in various forms. I read it at the Wednesday table read three times. Lorne and the writing staff liked it more than some of the hosts. Some of them didn’t necessarily get it. Martin Freeman kept asking if we were going to black up, which is a term I was not familiar with, but it’s British for put on blackface. And I kept saying, “Absolutely not blacking up, sir. No blacking up is going to happen.” When we finally shot with J.K. Simmons, he didn’t read it at the table, so he was given a script, told to get in a car, and go to location. He came up to me, and said,  “So, I’m Nas.” And I’m like, “Yeah.” And he’s like, “Does it matter that I have no idea who that is?” And I said, “No, actually, that’s great.” And he said, “Who are you?” And I said, “I’m Jay Z.” And he said, “Okay, but we don’t do impressions?” “No.”

What was the original pitch like?
In its description, it never does well, so I never described it to anyone. I literally read the eight- or nine-page sketch out loud with the rest of the cast at the table read, and then people could get it a little better. Especially once it gets to where Jay Pharaoh is next to me doing a really good Jay Z impression, then people are fully like, Oh, this is 100 percent aware of its incorrectness.

I went up to Jay Z himself at SNL 40. I was sure he’d seen it, because, without being arrogant, people’s assistants always show them. And he hadn’t seen it apparently, so it made no sense when I introduced myself like, “I played you on the show, as you know. I’m Mike.” And he kept going, “Uh-huh, it’s all good, man, all good,” shaking my hand, like, Little note to myself, I have to figure out what that white guy was talking about. Because if you explained the idea to him, he’d be like, “That doesn’t seem like a thing that should be on television.”

Do you remember where the idea started?
I’ve definitely seen some bad biopics. A channel will do one and it’s just a half hour slapped together. It just lists where they’re from and their main five songs. I remember one growing up. It was John Denver and he would get into a fight with his wife or something, and each big fight or big romantic moment clearly led to a John Denver song in a cheesy way where even the main lyric would be said in the argument. You’d see him get his little aha moment. So I liked that.

And then the race thing was a little more complicated, and not necessarily something I sought out to do. During it, I just thought it’d be funny and awkward. But if I had to break it down, it probably has to do some with almost the shame and stress I felt being a cast member who is white, didn’t do any impressions, uncoordinated, can’t really sing or dance. I can’t do a lot of the things that great SNL cast members should do. I can come up with weird concepts and commit to them awkwardly, is that cool?

It’s also a classic high-status, low-status way of you taking these giant figures and playing them, removing the incredible charisma they both have. Same thing with Oprah. 
On the purest and most basic level, it isn’t even about race. This dorky, sweet Midwest guy has none of the coolness that Jay Z and Oprah have in everything they say and do. So it’s fun to juxtapose the cool and uncool.

When you thought of doing a second one, did it start with Oprah?
They were a little bit one and the same. As soon as I started thinking about doing another one, it was a short list pretty quickly, with Oprah pretty much alone at the top. I thought to heighten off of Jay Z, it should be a woman. Although I was thinking about Gandhi a lot. I watched that movie and everything. The sets would be too hard, but I did really like the idea of being like, “I’m so mad at the British government, I’m not even going to have lunch today.” But then when you go for the women, it’s like Oprah, Hillary, Taylor Swift, Malala. I am basically like the same height as Taylor Swift and same complexion, and other than the Kanye thing, how many bullet points would like my dad know about her? So I started asking my dad if he knew who Stedman is, and he did. Everybody knows like ten things about Oprah. Everyone knows she was in The Color Purple and nominated, everyone knows the book club, the show, her own network, the giving the cars away, Tom Cruise jumping on the couch. There are just so many household things that it quickly became the most obvious choice.

Do you start with the list and then filter it through the worldview of these trailers one by one?
Yeah, I do a bunch of research, and then I’d cut myself off before I start writing, so that I get it all half wrong. The timeline is a little out of order. Same as with Jay Z, he gets congratulated on The Black Album as if it’s his first thing, and so on. So I’d watch the scene in The Color Purple once and then try to rewrite it in my own voice without having the script. There was the thing in doing too much research, because I found out a bunch of stuff about her that no one actually knew. The only thing that stayed that people didn’t realize is that she was Miss Black Tennessee. I thought that was a neat thing, and a good way to kick it off anyways.

Since it’s a similar joke throughout, how do you try to escalate it so there is momentum?
One of the things we tried to do and didn’t succeed in is getting more absurd casting. We asked some people, like Whoopi Goldberg, to come in and be Lance Armstrong in the interview where he comes out as having used steroids. But they were very busy. Everything with SNL is always like, “Can you come over right now and shoot?” And the people are like, “I need weeks.”

The other thing we tried to do, without it going over the top, was trying to embrace the fact that it’s a woman and not have laughs about drag, but just showing how not graceful I am. I’m not a powerful feminine force like Oprah.

It’s funny that you mentioned the drag thing, because whoever did wardrobe really nailed it. Everything fit very nicely and it was very funny how grounded the clothing felt on you.
The whole department is insane, but especially Jill Bream. [She] was in charge of it, and she did Jay Z as well and got so specific. A lot of them are the exact outfit from that famous moment. And then she took those 15 outfits and tailored them all to me. Fifteen legit Oprah outfits.

Did you write a bunch of related scenes and then shoot all of them? How was it actually shot?
The script that we read on Wednesday had most of what you saw on Saturday. On Thursday and Friday as we’re shooting there’s a lot of like, What if we did a Lance Armstrong beat, but it’s someone like Whoopi? And I would just write the three lines on my phone and send it to the talent department to reach out to Whoopi with it. But we had most of it.

And then, the first look at it is too long, so we had to cut it down. Jay Pharoah did a great Stedman, and just in losing time between dress rehearsal and air, we had to try to cut everything down to make room for the other sketches. Stedman had to go. It played around 10 p.m. in rehearsal and then I had to run up to the editors on the 17th floor and say, “Lorne said it took too long before people got the joke. Let’s cut out this, this, and this.” An editor yanks those out, you look at it, then you remix sound and send it down to the booth to go on the air. On Sunday you’ll be like, God, I wish I’d had an hour to sit and think about that.

How did it play at the table on Wednesday? Especially how it compared to how Jay Z played.
I think Jay Z probably played better, and it was comedy writers being surprised. Here they weren’t surprised. They were like, Oh, he’s gonna do this again. Let’s see the moves he does. I’d say Leslie Jones was a big fan of me saying The Color Purple speech, so that felt good. Not that getting an enthusiastic laugh from Leslie is impossible. She brings a great energy in that way. I was happy they got her. I like when she physically assaults people around her.

Did you feel like it was important to get Jason Sudeikis back for this? He’s part of the universe?
Yeah, that’s exactly what I was thinking. He was just so supportive about the Jay Z one, and I wanted to at least make sure to ask him. He still lives in New York, so it was an easy thing to check right away. “You’re Whoopi in The Color Purple. And he’s like, “Sounds good.”

There is a thing that SNL does a lot with its fake trailers that you don’t do in these, which is have a beat towards the end where you undercut the premise. You know, like have their be a voice-over that says, “Blah Blah from the New York Times says, ‘What the hell was that?!””
You’re right that it does undercut itself more often than anyone else, and yet a note we get extremely often is “Don’t undercut your piece.” So the fact that is still happens is funny to me, and probably not what Lorne and the producers would want us to lean towards. You begin by trying not to do that, but then if you just have a bunch of review jokes that get some of the biggest laughs at the table, you leave them in.

It happens a lot in commercial parodies. At the beginning of the show, in the commercials they never showed the actor make a gross face or something. When Laraine Newman takes the drink of the fish, she gives a big smile. We can see it’s gross but no one in the production of the commercial ever acknowledges that this could be a gross thing. However, it’s really, really tempting, especially after a while, and the actor does an improvised take that undercuts the product and the crew all laughs. It’s just tempting all week, because it’s such a nice relief. But to stay as true as you can has its own rewards.

It’s hard because they so often work.
It’s either usually (a) there’s a great joke there that made everyone laugh or, (b) holding the hand of the 8 o’clock dress audience a little bit so that they get it. If we put the New York Times [joke in], the 8 o’clock audience might have felt safer and laughed harder at the rest of it. I don’t blame anyone who does that because, oh man, I don’t know who the people are in the audiences, but they’re definitely not comedy connoisseurs looking to push the envelopeSometimes you just have to be like, “Look here’s the deal on this one, okay? I know it’s not a recurring one. I’m sorry that Kristen Wiig isn’t here tonight. I know you thought she was in the cast still. There’s this guy and he’s doing this thing,” and you just lay it all out for them. Everyone’s always like, “God, you guys do too many game shows and talk shows,” but those are so clear from the beginning, and it’s so clear what the joke is that the audience is like, We’re safe. We get it. We get to enjoy it. And there’s something to be said for that when you’re trying to win over the crowd in a minute or two with a brand-new comedy bit.

That must be the case especially if it’s edgier: This is what the whole thing is. We’ve thought it out. You’re in safe hands. It isn’t racist. We’ve thought about that too. 
It’s like the “God is not gay.” They didn’t undercut it at all, and I think some of the live audience had trouble with it, like, Is this at all making fun of gays? Or are they mocking the people who are passing these laws that allow the homophobic actions of some businesses? It’s a little touchier subject than the fun-loving SNL sketches that they might have shown up to see.

Back to the biopics, do you think you’d want to do another of these? Or is the well empty?
No, that well’s empty. That’s as much as we can do. If I went to India, a Gandhi one would be fun. But it’s gonna be a couple million dollar production. But no, honestly, I think two is plenty for that joke. I was lucky and happy to get a second one out of it. But I’m going to retire from my impressions for real now.

Mike O’Brien on His Jay Z and Oprah Sketches