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I’ve been a Sara Schaefer fan for a while now. Much like hearing a musician you like, you start to follow their music, an author you like, your read their other books, etc. The same goes with bloggers. Eventually you come across someone who has the same sense of humor as you, makes all the witty pop culture references you regurgitate to your friends as your own, and you end up relying on that person for next day funny coverage of everything you watched the night before. That happened to me with Sara four years ago or so, when she was writing for BestWeekEver.tv. So when she became the head writer for the Late Night with Jimmy Fallon blog, (who I think has the best late night show currently on) I was not surprised and very happy. Sara was nice enough to take some time and talk to SO about Late Night, being a stand-up in NYC, viral videos, and other fun subjects. Enjoy.

Serial Optimist: Hey Sara! Really happy to have the chance to interview you, thanks for taking the time! I first became a fan of yours a few years ago when I had BestWeekEver.tv bookmarked and checked it daily. You know what’s weird, is that I never knew what you looked like, but for some reason I always imagined you being really cool looking. I literally can remember always reading your posts, and thinking, “Sara Schaefer, great name, I bet she’s real cute.” I was attracted to the name of person I knew nothing about except that I found you funny. I’ve since seen pictures, and you are cute! You are cool looking! So it all worked out in the end. So my question is, what is your current must watch, can’t miss, favorite show on TV right now?

Sara Schaefer: I have many shows that I can’t miss right now. Real Housewives of Atlanta and Beverly Hills, Gossip Girl, Bored to Death, Oprah, Grey’s Anatomy (I can’t quit)…those are the main shows. There are other shows I know I should be watching and that I want to watch but can’t keep up.

SO: How and when did you get into comedy?

Sara: I guess it officially started in college, when I joined the sketch comedy group at William & Mary. From there, I ended up in New York with the intention of pursuing it as a career. I had to work a full time job for many years before getting anything that paid – but at night I would perform – hosting, improv, sketch, storytelling, my own stupid version of standup, videos, anything and everything. About 5 years in, I landed a gig hosting a show for AOL, wherein I interviewed tons of bands and made comedic videos about music. From there, I got the job at BestWeekEver.tv, and then from there, Fallon.

SO: You have had such a big online presence for a while now. How did that come about? Why have you as a comedian/actress translated so well to the online platform, especially blogging?

Sara: I was lucky to tap into the internet early as a source of income – I landed at AOL right when YouTube had exploded and just after ‘Lazy Sunday’ happened. I remember when I got it, feeling a little like “Well, it’s just the internet. Who cares?” But then it became obvious I had found an interesting path into comedy as a career, and it was legitimate. Since then, it’s been so awesome to get jobs that are attached to TV shows, and I’ve been able to learn so much about television production, late night, and comedy writing and performance for TV. And how those things are becoming more and more connected to an on-line experience. Especially at a show like Fallon, which has fully embraced that idea. I’d love to make the transition from the internet to TV, because when I was little girl, there was no internet, and I still hang onto that childhood dream of being a comedian that performs and writes on TV. But I also just want, one day, wherever I end up, to look back and be able to say, holy EFF that was fun. So wherever this all takes me is fine with me!

SO: How would you describe yourself as a stand-up? What kind of comedy do people get when they come and see you perform?

Sara: I’ve only gotten really serious about doing more traditional style standup in the past 2 years – taking long-ass rambling stories and condensing them into more structured shorter things. I think I’m very honest, and I purposely strive to be authentic.  It’s very hard for me to lie in my jokes, even if it’s an easy way to get to the laugh.  I challenge myself to find the words that make the truth funny. When you’re so vulnerable like that on stage, however, it’s hard to figure out what your voice is, because you’re always in it and can’t look at it objectively and point at it and go “that’s a character I created, which is modeled after my mom” or what have you. A friend of mine recently described my act like this: “It’s like you’re a little girl performing in front of the mirror.” Which sounds adorable! But I have no idea.  I’m just starting to figure it all out, and it’s exciting.

SO: WATCH OUT! Guest question from Broad City’s Ilana Glazer: I’m somewhat preoccupied (re: obsessed) with the fact that straight white men rule the world and, subsequently, TV & the Internet.  I keep this demographic in the forefront of my mind when writing & performing; sometimes it guides my comedic decisions, and other times it influences defiance. I’m wondering what your relationship is with this reality. Like when you decide what to wear for stand-up, do you like to feel pretty, or do you specifically want to NOT feel pretty in order to feel funny? Do you ever inject titties (or sets of titties) into videos or something to make it more viable for mass audiences? How does it affect your process, at least in standup?

Sara: Ilana will tell you that I could go on about this topic for hours! I have had my heart broken by the boy’s club at times, and I can get angry at it and what it does to women comedians (and what it makes us do to each other), and even the stupid articles that seem to get written every year about the topic.  (I’d rather it just not be an issue.) I always put it this way: If I had a choice, I’d much rather be nominated for “Best Comedian” and lose, than to be nominated for “Best Female Comedian” and win.

Regardless, I try not to take a decidedly feminist or non-feminist stance in my act. And even though I have made little personal decisions along the way about how I’m going to handle being a girl in this world, I try hard not to judge what another female comedian is doing solely based on the fact that she is a woman. I try to ask myself, “do I find this person funny and/or inspirational?” and if the answer is no, then move on.  It’s hard, though, to not let your own insecurities take over when comparing yourself to another comedian – male or female. Basically, this is a vague way of saying “I think Ilana Glazer is a SUCH a bitch.”

SO: How has the experience been being the head writer for the Late Night With Jimmy Fallon blog? How involved are you with the show? Late Night is by far the most “hip” late night show around, with his blog, online presence, The Roots, the style, everything. Does that just come with having a more youthful host and writing staff? Was that a plan all along, to really create not just a late night show but kind of a cool, viral heavy show that really connects with a younger demographic?

Sara: I am so in love with Late Night. It’s been the greatest, coolest, most fun, and most challenging job I’ve ever had. I am very involved in the show, which has been amazing. The show started on-line – and so from the beginning I’ve worked very closely with Jimmy, the writers, and the producers. Of course, I know my place: the blog is always in service of the show. And that’s how it should be. It’s been so exciting to be the conduit between the audience on the internet and what’s happening here at the show. I interact with fans directly, and with the show all day long. I can speak to both sides when we’re in a meeting and planning a new interactive thing on the show. I have learned so so so so so much, about, well, everything. And I really credit Jimmy with pretty much all of the show’s success – on-line and on-air. He just gets it, and he’s so universally appealing, and genuinely funny. And he has surrounded himself with some amazingly talented and diverse people.

SO: How much stand-up are you currently doing, like a weekly/monthly basis? Do you still participate in theater at all, or have a desire to?

Sara: I perform as much as I can – some weeks it’s every single night. I don’t do any traditional theatre, but I enjoy seeing it on occasion!

SO: What is the best viral video of 2010 so far?

Sara: Oh shit now. That’s a tough one. I mean for me, it has to be a tie between ICP’s Miracles, Double Rainbow, and Antoine Dodson. Or Iguana farting in the bathtub.

SO: What is the best thing about being a stand-up comedian in NYC? What is the hardest thing?

Sara: NYC is the best place to get good at stand-up. I’ve just started performing in other cities and I can see how strong it has made me when I arrive on a new scene somewhere else. There are just so many ways to get stage time here, and also the crowds here are weirdly hard. What would kill in Middle America will bomb here – so you’re forced to be that much better to get those laughs. So in some ways, the best thing is also the worst thing. You have to be ready to fail a lot and to struggle with a lot of tiny, yet terribly painful rejections. But when the hard work pays off, you feel all that stuff dissolve away, at least temporarily.

SO: If you were to have the perfect kiss in the perfect setting in the perfect moment, what song would be playing in the background?

Sara: The soundtrack to ‘Last of the Mohicans’.

SO: Love it. Thanks Sara!

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SO Note: Check out Sara’s website at www.saraschaefer.com, follow her on Twitter @saraschaefer1 for smiles, and of course read the Late Night with Jimmy Fallon Blog!

*Photo by Jeffrey O. Gustafson