Interview Double Digest Part Two: Cindy Chupack

In case you missed it, yesterday I posted an interview with writer Andrew Solomon that I think is quite good if I do say so myself. Also, Chicagoans, the lineup for the next Funny Ha-Ha has been solidified for August 21st. You don't want to miss it--save the date. We're going to be featuring standup comic Kumail Nanjiani, who I profiled in Chicago magazine here. Finally, if you're a fan of "So You Think You Can Dance" (and seriously, it's a fun show), tune in for my thoughts on the show here.

Every so often I interview a woman on this site whose career I would like to hijack as my own. Today's is one of those. If you watch "Sex and the City" on syndicated reruns several times a week as I do, you probably recognize her name as a producer and writer (and Emmy and Golden Globe winner). Before that, she was the author of The Between Boyfriends Book, a writer/co-executive producer for "Everybody Loves Raymond" and contributed to numerous publications including the New York Times, Glamour and Slate. Most recently you can read an essay of hers about a "bittersweet reunion" with her gay ex-husband in the anthology Girls Who Like Boys Who Like Boys: True Tales of Love, Lust, and Friendship Between Straight Women and Gay Men and catch her this summer as a columnist appearing in O Magazine.

The Cindy Chupack Interview: Slightly Less Than Twenty Questions

Did you discuss the essay you published in "Girls Who Like Boys Who Like Boys" with your ex-husband before it was printed? How did that go?
Hmm. Do we have to open with this question? This is a constant source of anxiety for me, because as a writer who writes mainly first-person essays (when I'm not writing television, which is at least fictional characters performing scenes from your life), I always feel like I'm writing partially for my smart, funny, friendly, mostly female audience, and partially for the person I'm worried might not like seeing it in print. (This person is often a parent in my mind, even though my parents have always been supportive of my writing. It's hard to write about sex and not wonder what your parents will think.) Of course. I know as a professional writer, you can't focus on these things, but I do. So with this piece, which is very personal and also very complimentary of my ex (I felt like it was closure for me and a valentine to him), I only contacted him right before the book came out, because a shorter version was coming out in the New York Times Modern Love column. He was very nice, and said I could write whatever I wanted now, even use his name, that he finds it funny at this point... but then I never heard from him again. And it's been a while. And here I am writing MORE about him. No wonder he's annoyed... or hopefully just very busy.

There have been several famous women who've married gay men (or men who everyone suspects is gay). Do you think they're publicly perceived differently than, say, women who marry philanderers?
It's an interesting question. I think the issue for people is always: Did you know going in? If you knew your fiance was gay, or was going to cheat, would you sign on to marry him anyhow? Is that a bargain you two somehow struck? It seems sad for a woman to go into a marriage with that knowledge, but then again, would you rather be surprised (as I was), later in life with one of those discoveries? So who knows? You can't judge people. It's tough out there, and a lot of gay men are pretty fabulous, and a lot of straight men are kind of boring, and a lot of straight, boring men still cheat, so who cares what the public perception is?

What are some of your favorite other essays from the anthology?
I love so many of them, but especially Anna David's because she is so hilariously doggedly determined not to let this guy's sexual orientation get in the way of their potential relationship. I also love Philip Himberg's, where he describes a life-long friendship with his first girlfriend, who eventually has a baby for him and his partner. At one reading we did in LA, someone asked Philip how his daughter felt about all of this, and he said, "Why don't you ask her?" and then his daughter, who is 15 now, and very cool and self-assured, said she just feels very loved. She said she has two dads and a mom she sees four times a year, and it's all she's ever known, and she feels very lucky... and very loved. (And if that doesn't make you want to rush out and get the book to read Philip's essay, you should also know that it is the first piece he ever had published. He's had a lot of creative success in other areas, but this is his first time out as a writer, and the piece is so beautifully written you can't believe he hasn't been writing all his life.) I also love Zach Udko's funny and poignant piece about his mother coming to terms with the fact that the son she basically raised on Broadway musicals was gay. (Zach was a student of mine when I taught a writing class at NYU, and he's the reason I'm in the anthology... he told the editors about my story.) I also love Gigi Levangie Grazer's piece about her friendship from afar with a gay waiter at the Ivy. The anthology is really lovely... lots of amazing and funny pieces about the special bond between straight women and gay men.

Tell me one thing you liked about living in Evanston (my home town)
You do your homework, huh? (I lived there while I was at Northwestern.) I liked that Breakfast Club was filmed there. And I liked that Evanston was near Chicago, but not in Chicago, because for me, coming from Tulsa, Oklahoma, it was a baby step toward moving to a big city.

What are your favorite TV shows on the air right now (other than the ones you work/have worked on?
I LOVE Friday Night Lights. That's just extraordinary television and I hope it gets the audience it deserves. I also love The Office (the British and American version), 30 Rock, and a new HBO show I just started watching, Flight of the Conchords. (The series and the HBO special those two New Zealanders did are really fresh and funny.) I will also admit to you that I, Cindy Chupack, watch quite a few reality TV shows like Intervention (I'm going to need an intervention to stop watching so much of it), Extreme Home Makeover (when I need a good cry), Project Runway (fun for the fashion) and the Biggest Loser (I used to sometimes eat dinner while watching that, which made me the biggest loser of all).

Writing for television seems like it's exhausting: does it take a person with a lot of stamina and a competitive spirit to stay in the game or is it more about the ideas and the writing?
It does take a lot of stamina and a competitive spirit, both of which I barely have anymore. That's why I'm mostly home these days writing my first screenplay and working on my O, The Oprah Magazine column and procrastinating both of those things by agreeing to be interviewed for blogs. I think FILM is more about the ideas and writing, because you can write a screenplay on your own time and be done (or be kicked off the movie when they hire other writers to rewrite you). Television is really a more-than-full-time job. You have to play well with others, and be in the writer's room, and as you move up you also have to be in editing and casting and on the set, and it's all very exciting except that I barely have the energy to write to you about it, let alone do it these days. I was working on one show early in my career that was at least 80 hours a week. Howard Stern used to be on the radio when I was leaving. I will have that energy again, I'm sure, when the right idea hits me and I have a lot to say about it, but for now I'm enjoying just consulting or freelancing for shows I like. (Let someone else be in charge for a while!)

If you had to pick one genre and stick with it, which would it be?
I don't think I could pick. I like cross-training... having the option to write an essay, a television episode, a television pilot, a movie, a children's book, a Broadway musical, or just an e-mail to a friend. Adriana Trigiani , a New York Times bestselling author who used to be in television, once told me that it's like finding the right vase for whatever you want to write.

Of your many projects, which is your favorite to talk about?

I love talking about Sex and the City, which is funny, because people always assume I'm tired of talking about it and don't really ask much anymore. But that was the greatest creative experience of my life, plus I loved the other writers (they are still among my best friends), and I loved everyone involved. It was just a magical time, and I'm really proud of the work we did on that show, and the impact the show had. Even when it was happening (as opposed to only in retrospect), I was aware of how special and perfect the experience was.

If you could keep your same job but live anywhere in the world, where would it be?
Wow. I love that question. I basically COULD do this job from anywhere in the world, but my husband, who also loves to travel and wanted to live abroad someday, got a job with the LA Public Defender's office and talked me into getting a St. Bernard, so somehow they're the reason we're stuck in Los Angeles, even though we came back for my career! But if we could be anywhere (I guess the dog, too) I would love to spend our time between the Four Seasons Chiang Mai in Thailand, the North Island Resort in the Seychelles, a villa or cooking school in Tuscany and the Four Seasons Hualalai on the Big Island of Hawaii. Okay, for a girl from Oklahoma, how spoiled am I? That list is like an issue of Travel and Leisure, I know, but I've been lucky enough to visit (on my own dime!) all of those places and the combination of natural beauty, amazing food, crazy nice rooms and views... how great would it be to live and write in all of those places? (Note: I say "on my own dime" because I still have that same feeling I did the first time I bought a sort of expensive sweater -- $60 was sort of expensive then -- with my waitressing tips in high school. I still love, as a woman especially, that I make my own money so I get to decide how to spend it.

What's the biggest misconception people have about what it was like working on "Sex and the City"?
That I must be tired of talking about it. And that the actresses wore those shoes all the time. They usually wore Uggs and then put on the Manolos when we started to roll film. And people often think each writer wrote for one character, but we all took turns writing entire episodes. Is this terribly boring??? Am I supposed to be funnier?

Did you get many acquaintances contacting you during the show asking if certain characters were inspired by them (and were they ever right?)
I didn't get that, but on dates, men would often say, "Are you going to write about this?" and I would often think, "Oh, if only you were that interesting."

In your opinion, how does HBO net such well-crafted shows? Is it that the people who work there have a good eye or that it's simply developed such a reputation that certain directors/producers know to pitch to them?
I think it all started because the HBO executives had a great eye and trusted their instincts (as opposed to relying on audience testing, or programming for what they thought an audience wanted). And because of that, HBO became the place where you do your passion project, because you get the full half-hour or hour with no commercials, because they spend the money to do shows right, because since it's cable there's more creative freedom, and because during the development of a show, there is much less network interference and second guessing. It's a place where you won't make as much money, but it's a place where good writers can do good work, and for more and more writers (including me), that's what matters.

I've noticed that some of your inspirations are Merrill Markoe and Wendy Wasserstein. What other female writers or comedians inspire you?
I love Julia Sweeney's one-woman shows, which are available from her website. She is everything I aspire to be... fearless, honest, soulful, smart and hilarious.

What do you make of the starlets who flash their vaginas or crash their cars or get attention just by not eating...harmless entertainment or a more sad/sinister sign of what young women look up to?
I think it's mostly a sad/sinister sign of what's become of those particular starlets, and what the limelight can do to you. I would hope that young women would be able to see that also, even if they can't help but be fascinated by it, since we seem to be on a Paris/Nicole/Britney newswatch 24-7. At the risk of sounding 80, I don't understand why there isn't more responsible reporting about these things. It's like we're all appalled, and yet, we can't get enough of it. That said, there was a great HBO documentary (and coffee table book) called Thin by Lauren Greenfield about women in a Florida clinic for eating disorders, and it has really haunted me. You can't minimize what terrible diseases anorexia and bulimia are, and how hard it is to recover, so I would put that in a category separate from the other attention-getting antics.

Has your experience thus far writing for O (although you don't debut until August, right?) been very different than that for other magazines?

Yes! And I'm not just saying that. The editors at O have been very respectful of my writing (which is not always the case) and they don't just want a tidy little takeaway message, so it's been a pleasure so far. They are basically letting me say what I want on sex and romance, and not censoring, and helping me solicit REAL reader questions each month, and I like the tone and message of the magazine. I think it's very empowering and thought-provoking every month.

What's the scariest thing you've done thus far in your career?
What I'm doing right now (or not doing right now!), writing my first screenplay. I'm adapting Nick Hornby's novel, How To Be Good, and there's something about writing a movie that makes me a little nervous, maybe since it's four times as long as a half-hour of television, so I feel it needs to be four times as good? Maybe I feel like it needs to say more, and be about more than anything I've written so far? And this is my film debut, so I want it to wow people, even if it never makes it to the screen (which often happens with screenplays, although I keep thinking this will because Laura Ziskin is producing it, and she produced Spiderman, so she knows how to make things happen). Also, I've been very cautious about what I wanted my first film project to be, and this finally felt like the right project, so here we are... and now it's just me and the page! Plus I love Nick and his writing, so I want to do right by him and the book. And there's the issue of an adaptation being a little more complicated than an original screenplay (what to cut, what to leave in), but it's also easier because there's a great blueprint, but then you have to live up to that blueprint! Yeesh. Can you see why this is difficult, or at least, why it's difficult for a neurotic writer like me? However, the baby writers who worry me the most are the ones who don't worry.

Tell us about the screenplay that you should be working on right now instead of answering these questions?
I just did. Don't you listen?

Okay, what I love about this project, How to Be Good, is that it's about how to make a marriage work, and how much of yourself you have to let go of in order to be a wife and mother. It's perfect for me, because it's an exploration of the questions that I'm interested in post Sex and the City... How do you make love last? Once you've got the husband and kids, then what?

How does it feel to be the 184th person interviewed for
I'm wondering if you've interviewed a few more in the time it took me to get around to this, but in any case, I am honored, because you've interviewed some of my favorite people, so I feel like I got into a really great party. Now where's the bar?

More interviews here!