I love a funny woman. I was a fan of Ali Wentworth first. It was during a late-night airing of The Tonight Show with Jay Leno, circa 1994, when I first saw her: this strange, bold, wonderful animal. She was cute—all blonde hair and big eyes—a kooky energy. Then I saw the braces.... I think this is true, or maybe I just created it in my fantasy of Ali’s oeuvre, but she was in the audience, and I was confused. Is this real? Is this a skit? Then I saw her on Leno again, and she did this bit on supermodels, and I fell in love. She was subversive. Ali was clearly an über-smarty-pants and played the supermodel persona to the hilt, but she was fearless and unapologetic, and ironic and subtle—and then not. And did I say cute? I became vaguely obsessed.
Years passed, and I saw that she was acting in TV shows and movies and marrying the brilliant strategist George Stephanopoulos. Then came the books. And, of course, in between there she had two gorgeous daughters and became a Martha Stewart mini-me. It was around this time I actually met her. Our mutual, dear friend Mariska Hargitay said to me one day, “You know who you have to meet? Ali Wentworth. You would love her. She is the funniest person I know.” Stifling the impulse to say, “What am I—chopped liver?” I smiled and said, “I’d love to.” Ali was living in DC; I was in LA, but Mariska got us together through her Joyful Heart Foundation gala, and a friendship was born. Yes, she is hilarious. She makes me pee in my pants a little on a regular basis. But, more importantly, she is a good soul. She is generous and welcoming, focused and serious, playful and enthusiastic, devoted and proud. She loves her family and protects her friendships. She is intellectually curious and ever finding outlets for her boundless creativity: Daily Shot with Ali Wentworth (a Web series on Yahoo), more books (Ali in Wonderland: and Other Tall Tales was published in February), a crafts room. If I didn’t love her, I’d hate her. She is an inspiration and my good-time gal, and I’m so lucky to have her as a friend.
DEBRA MESSING: You always wear your glasses. It seems like you love to wear them because it adds a little journalistic seriousness to you.
ALI WENTWORTH: But, also, I don’t like to wear makeup.
DM: And yet, you’re putting it on all the time.
AW: I put it on, but if you’ll notice, when I wear my glasses I don’t put on eye makeup. I actually like to wear them because I don’t feel like putting on mascara and eyeliner. But also, you know, I’m getting my eyes done.
DM: I do know that. Are you nervous?
AW: No, I’m very excited—for my “corrective surgery.”
DM: Yes, for your “corrective surgery.” Do your girls know? What did you tell them it was for?
AW: The dilemma was how to not make it about vanity even though it is.
DM: Exactly. So, what did you tell them was the non-vain reasoning for your procedure?
AW: I said to them: “You know Mommy doesn’t work out. Mommy doesn’t wear makeup. And you have to tell Mommy that her roots are so black that she has to do something. So Mommy is not very self-involved.” To the point where they wish I were more. I said, “It’s not like I’m feeling old; it’s just it has been 20 years since Mommy has been angry about this. And I finally decided I’m going to do something so I don’t look so tired.” I’m not going to get a face-lift; it’s not about that.
DM: And they thought it was cool?
AW: They were like, “Yeah, we get it.”
DM: So, what made you finally decide to take the plunge?
AW: I’ve been talking about this for so many years. My husband, [George Stephanopoulos], is just like, “Get it done, Ali. Let’s move on to the next topic.” I was constantly looking for information. I like to be prepared. How much pain is it? There was no information available. I was shocked that for something that is so common—that of course nobody likes to talk about—I couldn’t even go online and get a sense of what I would look like the next day, the next three days, or the week after.
DM: You know, you’re prepared for everything. You’re Supermom. I think that’s all about trying to make Martha Stewart shake in her boots.
AW: She is getting up there. Her show was just canceled.
DM: And yet, your Web series Daily Shot is up and thriving!
AW: 850,000 hits a show.
DM: That’s amazing! And okay, so tell us how it came about.
AW: Disney called me and said, “We’re changing our whole online plan. We don’t want to be The Mickey Mouse Club. We really want to appeal to moms. And we think you would be a great person to,” as they said, “be our Barbara Walters.” So I said yes. They wanted to do a show per month. And this had just happened to me: A friend had just given birth to her fourth child, all under the age of six. It was during the Amanda Knox trial. She called me and said, “I’m really embarrassed. I’ve just started to go out to dinner parties. Who is Amanda Knox?” I quickly told her, and then I thought, there are busy moms who are not reading every paper every day. They don’t know what’s going on. Let’s do a five-minute show, and I will tell them what’s happening. We set out to do that show, and it’s changed because we now start talking about what topics are trending on the Internet.
DM: So, like zombies—which I don’t understand, by the way.
AW: Which part? Zombies in general?
DM: I don’t understand trending. It just means everyone is talking about it?
AW: Yes, that’s what it means. It’s getting the most hits and news stories; people are talking about it on Twitter. It’s just a big conversation. So obviously, [with the story about] two naked men, one eating the other one’s face, I couldn’t have been happier. I wanted the whole show to be about that. But they told me I couldn’t use the whole five minutes on that. And then, the Centers for Disease Control and Prevention had to make a statement saying that there is no virus that can reanimate life, meaning there’s no such thing as zombies, because people were literally getting scared and panicked.
DM: That’s incredible. And you say, ‘Awesome! Cannibalism, fabulous.’ That doesn’t seem to be in the realm of Disney’s normal...
AW: It’s not. And they would prefer it to be more [about] parenting issues. But, what happens if your kid faces a cannibal? They need to know!
DM: Do they have someone from Disney sitting in?
AW: They have a Disney lawyer, who is on mute, but listening. And afterward, she says: “You can’t say that.” “You have to say ‘allegedly’ that.” There’s a constant rub with Disney about what we can and cannot do.... I always back down. But I also think they want people to watch, and people are going to watch someone who is a little more provocative.
DM: What is the line that you will not cross on the show? Does it have to do with your children? Does it have to do with George?
AW: I decided that if I’m doing a show, it’s going to be from my kitchen table, and it’s around my family’s schedule. I didn’t think George was going to be part of it because he finishes Good Morning America at the same time we’re starting. I always say to him, “If you don’t want to be on camera, go around; don’t come in the kitchen!” And every day, he comes in the kitchen. I’m like, “Wow, you just got two hours of camera time on national TV, and you need to come sit and talk on my little Internet show that’s only five minutes long?” But he does, so I just go, “Alright.” But, I don’t like to have the girls on it.
DM: How do they feel about it being in the kitchen of their home?
AW: The kids are fine about it. Disney and Yahoo would love to have a lot more of them on it. But it’s not a reality show. If it organically happens, great. I am a mom; I acknowledge them, but only when it’s relevant and when it works.
DM: What do you think is funny? What makes you laugh, and where was your comic aesthetic born?
AW: What makes me laugh is details—when someone tells a story or someone says something funny that is so specific, I laugh. To me, it’s the minutia that makes me laugh so hard. And—this has nothing to do with you being here—Will & Grace used to make me laugh my butt off. It got me through two pregnancies. I had morning sickness with my younger daughter, Harper. My older daughter, Elliott, who was three, would join me in bed, and we would watch Will & Grace every d ay. T here w as a scene where the two guys walk into a bar, and the bartender says, “What can I get you?” And they both say, “George Stephanopoulos.” It is one of those spiked moments in my life. My three-year-old looked at me and said, “Why do those men want Daddy?” And I thought, here is a page for the parenting handbook; I’m not prepared to answer. I said, “They just really like him; they really think he’s smart.” The situation in that moment was hilarious to me. So, you know, the life stuff is funny to me, but there are some shows that, still to this day, make me laugh.
DM: Was anyone in your family funny when you were growing up? Where did it come from?
AW: No! I think it was from lack of that, from growing up in DC during Watergate; it was very serious. I think sarcasm was what I started with. I started to find humor in the things they were saying. I would make jokes, and it was like, “Oh, Ali, you’re incorrigible.” Then I just plain got on the counter and did sketches, and it grew from there. Any comedian or comic person will say, when you get laughs when you’re little, that’s it. You’re done. There’s no other response. And then I went to NYU and did plays—serious plays—but I would do my character in a way that would provoke laughter. I realized that’s all I wanted. I don’t want people to cry. I don’t even care if they clap. I want people to laugh. That is the greatest thing I could possible get—more than money.
DM: So, how is it for you to write a hilarious book and not get to experience the laughter? The audience members are at home, by themselves, laughing out loud, and you don’t get to reap any of the benefits.
AW: It was very hard, but most of the stories I have told (either to a girlfriend or at a dinner party), so I knew they worked. But it was hard to sit down and do it that way. It’s not as fun as performing. Writing is very solitary—and somewhat depressing.
DM: Do you need that in your life? The solitary creative expression, or do you feel as if it has just come naturally?
AW: It’s come out of how my life has unfolded. I would love to perform all the time, but I live in New York, and a lot of the jobs I was getting offered were in LA, which I can’t do. I found that when I wasn’t performing, the writing not only satiated a schedule, it actually satiated me. I need to be doing something creative all the time. I don’t love writing as much as performing, but it does take care of that need.
DM: Have your girls ever said to you, “Oh, Mommy, stop being so goofy”?
AW: Daily. No, I don’t get “goofy.” I get, “Mommy, please don’t embarrass us.” Which I don’t! I’m not like Phyllis Diller; I don’t walk around with a rubber chicken in my hand. Elliott has that reaction because she’s getting to that age, whereas Harper is my greatest audience ever. I can say anything, and she laughs.
DM: Is there ever a time that your husband looks at you and gives you big eyes that mean “too much”?
AW: Yes. And he’s warmed over the years of our marriage. But there have been a few moments, for instance, at a dinner party at Henry Kissinger’s house. The conversation was about a dogma from 1831—clearly, nothing for me to sink my teeth into. George looked at me like, “Don’t you open your mouth—not now and not here.” But I got one out: The British ambassador gave Henry Kissinger a copy of some document from, like, 1705 as a gift. All the men were going, “Ooh, this 1705 document.” And I said, “Uh, by the way, that’s from all of us.” George gave me the look like, “That’s it; that’s your one.”
Another time we were at a dinner with Richard Holbrooke, and these big intellectual, political guys were debating the Middle East. It was going on for a while. Then there was a tiny lull—and I don’t usually plan; it just comes out—and I said, “Sorry, um, Julia Roberts got married today.” And, thankfully, everybody started laughing.... I was trying to say, “There are other people here with other interests.” Also, I just needed to make a joke. It was time. And it was very well received.... I know how to read a room. I don’t make a lot of mistakes because I get a sense of what’s right and what’s not.
DM: Why did you start coming to the Hamptons?
AW: I grew up in DC, so we’d go to Virginia. I had friends in New York, so I’d visit them here sometimes. George had always gone to the Hamptons; he wrote his book in the Hamptons. I love the beach, and George loves the beach, so we were always looking for homes because we love the beach so much. Now I have so many friends here, it would be hard to leave.
DM: How long have you had your house here?
AW: We got our first house about 12 years ago, and it was a teeny-tiny house in town. Then we sold it, and we got another house that was kind of in the “horsey” area of the Hamptons. Then we bought this house [in East Hampton] two and a half years ago. And this was George’s faith in me: I saw it on a February day in an ice storm; he wasn’t even with me. I just called him up and said, “I found a house.” George is not free-flowing with the cash, but we made an offer, we gutted it and re-did it, and we love it. We love it in the fall and the winter, too.
DM: Do you ever have holidays here?
AW: We have Thanksgiving here every year—25 to 30 people for turkey. It’s my big, fat Greek Thanksgiving. And we go play football with Mariska. I love it out here in the off-season. We don’t do Christmas out here because it’s too much. Santa Claus can’t cart all the stuff.
DM: What is your summer season usually?
AW: I have been here since June and stay through Labor Day. The girls go to camp, and I pretend that I’m going to get healthy, but I never do. And I wrote a book.
DM: Did you write Ali in Wonderland: And Other Tall Tales here in the Hamptons house?
AW: Yeah. And I just made another book deal, which I’m writing this summer out here. If they’re at camp all day, I don’t know what to do with myself. I’m glad to have a project; I’m glad to have something to write. Also, during the year, I don’t get to read books, so I’m trying to read this summer, too.
The other thing I like about the Hamptons is, if you want to be social you can, but you don’t have to be. It’s there if you want it, but you don’t have to. You could go out every night if you wanted—or not.
DM: What are some of your favorite places out here?
AW: Last summer we discovered The Crow’s Nest Inn & Restaurant and The Surf Lodge. There are these restaurants on the beach, so the kids run around the whole time while you’re having a cocktail and ordering. And then you eat, and they play. I love that. (Although we go to Meeting House a lot in Amagansett, where the kids have to sit down.) I love when they’re jumping in the surf and I’m talking to my friends, and everyone can have a great experience. Everybody gets what they want.
DM: And George loves it, too?
AW: George loves it, too. I love going to the beach. I love picnics on the beach. Last year I did a treasure hunt in the sand with like six or eight families. I’m not a big tanner, so I don’t like to go during the day with my blanket and olive oil and aluminum foil. But I like going at dusk with the kids and the dogs. And I love cooking, and so does George, so the idea of all this fresh produce; it’s fun to cook.
DM: Is the Daily Shot filmed in the Hamptons?
AW: Yes it is. We shoot four shows in two days, so [my cohost and series director and editor, John Carhart] spends one night a week in our guest cottage. We Skype on Fridays when he’s in Manhattan, and I’m here. It doesn’t really matter, in a way, where I am.
DM: As long as you have a kitchen.
AW: Yeah! John and I make it very summery, so one day we’ll have a lemonade stand with a tiny table and chairs. Maybe we’ll do it on my trampoline. We do different locations and sort of play with the idea that we’re not in Manhattan at the kitchen table.
DM: Okay, you dropped the bomb on us so we have to ask: What’s your next book about?
AW: My next book is a humor book on the realities of parenting. It’s not like a lot of these adorable books about it; it’s the real down and dirty. It’s like, what do you do when your kid says, “I hate you”? It’s kids and marriage and basically a lot of funny stories I have about being a mother, but there are also going to be chapters of other people’s stories. Like, what do you do when your 9-year-old, who is half Greek, has a mustache? Do you wax it? Are you telling her the wrong thing, that at 9 years old she should be waxing? Does that start a whole thing of self-involvement? Or do you say nothing, you’re half Greek, it’s ethnic. Things that I deal with as a wife and a mother; they’re funny stories but there is something to them. I’d love to be humorous but also have some takeaway that you can read it and actually learn something. It’s not a handbook, but it’s an entertaining read where you go, “Oh, I know what that feels like,” or “I’ve been there.” But also like, “What did Ali do?” Or “What did Ali’s girlfriends tell her to do?” We’ll be talking....
DM: Get the wine out.
AW: Oh, I know how to get stuff out of you!
DM: This was fun.
AW: I’m happy if you’re happy. You’re very good at this.
