Not many people move from comedy to the CIA; the agency’s hardly famous for its sense of humor. But when you think about it, a big part of spying is acting, playing a part in an unfolding drama. Emily Brandwin loved acting. She preferred any persona to her own. She also loved her Jewish mother, a wannabe spy. And she learned how good she was at thinking on her feet when she started doing improv with other theater majors at Washington University. They called their group Kaktabulz…
Kaktabulz is a terrible name for an improv group. Isn’t it?
Two of the guys made it up when they were drunk. We actually got some private gigs in St. Louis, though, including one for the Lemp Mansion, and we got paid! I also did improv with The Madding Crowd—we played at the Funny Bone and Union Station.
They say humor is born of pain, but you’re gorgeous, smart, sane…
I had my awkward years until I was about 30. There was just nothing right about who I was. I wore an eye patch in grade school, and then, of course, my other eye went lazy. I went to Clayton High School, and I was never one of the pretty, cool girls. The humor was protective; it gave me an edge.
You’re well past those years now.
My husband said, “Why are there no pictures of you from 11 to 28?” I said, “No one needs to know.”
But you’re still using humor.
It’s the tool to make everything better. Through humor, you figure out that nobody has that perfect, ideal life. My husband and I can fight, and 10 minutes later we’ll make each other laugh about something—it’s like a big reset button. And thank God, my parents and grandparents were funny. If you weren’t funny in my family, it was rough. When friends came over, I’d say, “I’m just warning you…”
So maybe your mom was joking when she told you to apply for a job with the CIA?
Oh no. She’s wanted to be a spy since she was 3 years old. They went to London, and my dad said, “You want to see Buckingham Palace?” and she said, “No, we want to see spies.” She thought she’d see men in trench coats standing in doorways.
Was spying a natural fit for you?
No! I was in special gym class in fifth grade for little girls who couldn’t throw balls. It was horrifying. She knew I had absolutely no motor skills.
Just what did that job listing say?
The title was “theatrical effects specialist.” OK, I was a theater major. I thought, “Maybe they teach acting skills.” I was very naïve. Then I started getting envelopes with no return address, asking questions about my family and more about my family and friends and places I’d traveled.
Your mom must have been thrilled.
I was working at Channel 9, helping with their pledge drives, and if there was mail from the CIA, she’d call and say, “The brisket is hot and juicy. The brisket is hot and juicy.”
What was the testing process like?
Hundreds of questions that are mind-screwy, like, “Would you rather kill your mother or your father?” Questions where there was no right answer and you had to make a choice. And personal questions about your sex life. I was very young, and I didn’t even understand some of them. After a while, I would just fill in the bubbles: “Oh, I haven’t filled in B in a while” or “If I fill in C and D, it makes a pretty flower pattern.” After 1,600 questions, you’re just dizzy. And then you sit down with the CIA shrink, and mine looked like Mr. Burns from The Simpsons—pruney, and not a bit of kindness in him. He said, “It says here you like to be tied up?” I said, “I couldn’t even climb ropes in gym class! I don’t even remember that question.” I had accidentally filled in the S&M bubble.
Were you mortified?
I thought, “Oh my God! What else did I fill in?” And then I got kind of excited. I hadn’t dated a lot. I thought, “If I’m going to be the Hester Prynne of the CIA, maybe it’s a cool thing.”
How long did you stay with the agency?
Years—I’m not allowed to say how many. First I created the disguises for spies who needed to go on operations—hide a giant birthmark, give them wigs or mustaches so they could blend in or stand out…
They needed to stand out?
Not often. But if you’re trying to distract somebody—it’s that idea that you walk around with a yellow boa, and then you take it off and nobody can find you anymore. Tony Mendez wrote about it in The Master of Disguise; the new Ben Affleck movie is about his life.
How did you go from creating disguises to wearing them?
You meet all of the spies; they’re your customers. Six or seven months into it, one said, “I think you’d be a great operations officer,” a.k.a. spy. I guess doing improv, being able to think on my feet and react quickly…
Maybe they’d intended that all along, and they were just testing you?
Oh, I don’t think so. My bosses weren’t thrilled. Recruiting somebody costs hundreds of thousands of dollars.
And then you had to be prepared for an entirely different job.
There’s a training course. The orientation was cheesy—an older woman was playing James Bond spy music on a boombox when we walked in! I can sound cooler in my apartment. And there were get-to-know-you games, and everybody says something about themselves nobody would guess.
So you went from theatrical effects to being a spy.
A covert employee. I had a covert job I could tell people, a really complicated, bland Department of Defense job. It’s overly boring, so no one will say, “Oh, that’s exciting! Tell me more.” Which makes dating really challenging, because you’re in D.C., and all of these guys are like, “I work on the Hill,” “I work for the FBI,” and you’re like, “I work in the basement of the Pentagon.” They’re like, “Next.”
For a while, I was trying to be creative, and I’d make up these exciting cover jobs, like “I teach public speaking. I teach the joint chiefs how to do public speaking.” People above me said, “Emily, there are people who actually do that!” I said, “I’m lying anyway. Why can’t I lie about this and get a date?”
Did your CIA bosses and coworkers have a sense of humor?
No—which was hard. I tend to gravitate toward people who are really funny and have that sort of joy and life in them. It’s such an überserious organization—and it needs to be. You don’t want people juggling in the halls. There are people who have a sense of humor there, but you kind of have to find them.
Wasn’t it daunting to do international espionage?
I truly didn’t understand what it meant. I got a little overwhelmed right before I started, thinking, “What did I get myself into?”
What helped most?
There’s an improv role called “Yes, and…” I think it’s the best role in life. My husband and I use it all the time. “What do you think?” “Yes, and…” It keeps you from being negative. And it’s great when you’re a spy: They tell you, “This is what you’re supposed to do,” and you say, “OK, yes, and then…” It takes away your fear.
I’d need more than that little phrase.
It’s a lot of mental preparation. And I trusted the people I worked with. Maybe I was in a dangerous situation, but somebody had my back.
The irony just struck me: Once you were a spy, you couldn’t tell your mother what you were doing.
She was absolutely dying. She would ask me all the time and want me to hint at things. And she’s hearing-impaired. So I’d be in my little cubicle at the CIA screaming at my mom. She’d say, “Are you going anywhere?” I’d say, “Yes.” “Where?” “I can’t tell you.” “But where are you going?” Oh my God. I’m in a cubicle at the CIA. I can’t yell at you.
When you quit, could your family tell people?
My grandma went to a Temple Sisterhood mah-jongg game. She came home and said, “I told my girlfriends.” I said, “Yeah?” She said, “Spy trumps doctor.”
Not to sound like your mother, but what can you say about where you went?
I traveled all over Eastern Europe and Europe during a time when it was a little heated; there were a couple wars going on. There was an adrenaline rush when I went: Here I am, this girl from the Midwest who used to do comedy at the Funny Bone getting on a plane doing something the government trusts me to do. And then coming back, I’d get terrified, fear and relief all at once. But part of the self-preservation is blocking that out until you’re done.
How did your time with the CIA change you?
I gained a ton of self-confidence, and the ability to take big risks and realize, really, what’s the worst that can happen? Before, I could get killed. So now the worst is nothing. I can “Yes, and…” everything now.
You saw a lot more of the world, too.
I’d never really seen poverty and despair on that level. I became much more empathetic. And it gave me a deeper understanding of what’s going on in the world. You’re at the epicenter; you see how the world works, and how different agencies work together, and the vying for position, everyone trying to be alpha.
Was the bureaucracy frustrating?
When something needs to get done, it gets done really fast. But the rest of the time, I don’t know how anything gets done. There was so much paperwork, and it had to be on cream paper instead of ecru. A woman pulled me aside and said, “Emily, you’re in a pissing contest, and you’re going to get all wet.” I said, “But it truly doesn’t matter what color—I just need a signature.” She said, “You’re not going to win.” “OK, fine. The cream form. I surrender.”
What finally made you quit?
Most people had wanted to do it since they were in the womb. I fell into it. I’d broken up with a boy. I’d missed out on a lot of family things, and I could never tell them why. I missed that normalcy, and I really wanted to settle down and have a family. I was almost 30.
Weren’t you surrounded by eligible men, though?
The agency becomes your dating pool, because these are the people you can talk to about your life. A lot of men at the CIA—you get trained to lie. They teach you how to lie and manipulate, how to get people to give you information, how to carry a different persona. So they have these tools now.
But so do you.
I kind of do. I moved to L.A. and started dating, and it’s all crazy actors trying to make themselves look better than they really are. I was dating a guy and figured out early on that he was lying about so many things, even his name. I said, “Your dates don’t match up for when you went to college. Did you graduate?” And he started fidgeting. When we broke up, he said, “You think you’re so funny. Why don’t you start doing comedy again?” I said, “You know, I think I will. I never want to see you again, but thank you for that.”
You’re still funny—I saw your Twitter posts (@CIAspygirl). And I notice you married a fellow comedian, not a spy.
Jeff Weinstock. He’s a vice president of marketing for ABC Family now, but he does do a little comedy still on the side. His is a more thoughtful humor—very smart, funny, maybe a little more cerebral. He can be very edgy, which I really appreciate. It’s not always safe. He’ll take risks.
