The central credo of Sleepless in Seattle is best summed up in a line that Rosie O’Donnell says to Meg Ryan: “You don’t want to be in love; you want to be in love in a movie.” Nora Ephron’s Oscar-nominated classic, released in 1993, doubles as a comment on the way Hollywood romance has perpetuated fantasies of what love looks like. And yet Sleepless is also very much a fantasy itself, and a lovely one at that. Playing Becky, the sappy, wisecracking BFF to Ryan’s destiny-agnostic Baltimore Sun reporter, it was O’Donnell’s second role after 1992’s A League of Their Own. Along a stacked ensemble that includes Tom Hanks, Rita Wilson, Victor Garber, and Gaby Hoffmann, she’s an MVP. Even the way Becky holds Cheetos, her pinkie raised as if they’re fine dining, is amusing. Together, the two movies made O’Donnell a star.
Although romantic comedies were thriving thanks to sensations like Moonstruck and Pretty Woman, Sleepless was seen as a sleeper hit. TriStar Pictures postponed its release from March to June, hoping the film would serve as summer-blockbuster counterprogramming — the same strategy that TriStar’s sister studio, Columbia, had employed for When Harry Met Sally four years earlier. The tactic worked. Sleepless saw the largest opening gross for a rom-com at the time and became 1993’s fourth-highest-grossing release. O’Donnell had been a successful stand-up comic, but her movie career soared after that. Eventually, she deployed her charisma as the host of one of TV’s best daytime talk shows.
O’Donnell, who recently moved to Los Angeles after years in New York and last appeared on Starz’s Run the World, remains one of our most forthcoming celebrities. Interviews are one of her gifts; she has a knack for peppering answers with interesting cultural references and specific anecdotes. So she called me up to talk about all things Sleepless, including the way Bette Midler influenced her performance, the time a crew member taped her monologue to his leg so she could get Ephron’s words right, and attending the premiere with her good pal Madonna.
Very few actors ever get two movies back-to-back that are as good and impactful as A League of Their Own and Sleepless in Seattle — and they were your first two! At the time, had you been trying for a while to get movie parts?
Well, I never really wanted to be a stand-up comic, per se. I always wanted to be Vivian Vance or Shirley Booth or Valerie Harper — I wanted to be the funny friend in something, probably a sitcom. That was what I was dreaming of. Or being a backup singer for Bette Midler. Those were the two things I had in my dream pile.
I was very lucky when I got cast [in Sleepless] and met Nora Ephron, who changed my life in so many ways for the better. We became close friends, and I lived in the same building that she did. She got me the apartment. So when I think of Sleepless, the first thing I think of is Nora. And then I think how amazing it was that three summers in a row I was in one of the biggest movies, because The Flintstones came out right after that. It was a pretty trippy ride. I don’t know that I was necessarily looking to be in movies, but I did not say no when they came around.
Had you been auditioning for a lot of sitcoms?
At the time, I was a VJ on VH1. Penny Marshall saw me and called my agent and asked if I could play baseball, so that’s how I got into A League of Their Own. And then out of League, Nora Ephron came and did a reading with me. At dinner, she said to her two sons and [husband Nicholas Pileggi], “I met this comedian-actress girl today; her name is Rosie O’Donnell.” And Jacob, her gay son, said, “Oh my God, I love her! She’s on VH1! She’s friends with Madonna! Mom, you’ve got to cast her.” So I always credit Jacob Bernstein with being in Nora Ephron’s Sleepless in Seattle. But I think it was a really fortunate, lucky three rolls of the dice.
When you were auditioning for Sleepless, had Meg Ryan already been cast? The list of actresses considered for her role is pretty substantive: Julia Roberts, Kim Basinger, Michelle Pfeiffer.
Yes, Meg was already cast. They were looking for Meg Ryan’s best friend in the new Tom Hanks–Meg Ryan film. I was like, What’s the chances I would be in two movies in a row with Tom Hanks? It was just out of nowhere from being a stand-up comic. I was just sort of thrown into it, in a way. It was such a Hollywood story.
Yeah, it’s that Hollywood Kismet — a perfect storm of things that vault you to the next level, so to speak. Both of these movies star Tom Hanks, and they’re also both directed by women, which was rare. And on top of that, both grossed over $100 million domestically. What did that mean to you, and feel like for you, at the time?
I knew that it felt like something for my agents, that they were very excited about that. They thought it was a good forecaster of your future work. Right after Sleepless was coming out, I adopted [O’Donnell’s first child] Parker. It was very much a family thing. Nora was very invested in the baby, and she really did create that family feeling. Her sister Delia was there, and they were writing it together.
Nora said a few interesting things about your role as Becky in various interviews from that time. First, she said she hired you because she felt like you would do for Sleepless in Seattle what Whoopi Goldberg had done for Ghost. Did she ever tell you that?
No, she never did.
How do you feel about that today?
That’s a lot of pressure. That was her Oscar-winning performance, was it not? I’m glad she hadn’t told me that so I could go in there and do the best I could. I was saying to people during interviews that they should give Bette Midler a residual check because I was copying the way Bette Middler walked, sort of the way she talked. It was an homage to Bette for me. When I’m walking with Meg in the park, I’m doing my Bette Midler walk.
That makes so much sense. Part of what makes Becky so memorable are the very specific, very feminine mannerisms that you give her: the way she holds her hand out, the way you raise your pinkie while eating Cheetos.
It was all Bette Midler! I kept thinking, What would Bette do? How would Bette spice up this part and make it come alive on the screen, which she’s so good at doing? Nora never brought it up to me or never asked what the inspiration was. It was like Eve Arden from those old films: the funny, caustic best friend with a heart of gold. It was an archetype, that character, and it was one that I had seen many times and always wished to play. The funny best friend was the goal when I was starting as an actor, and I was so lucky that I got to do it a bunch of times.
Nora also said she told you that you guys could rewrite lines if they weren’t funny. Do you remember ever doing that?
I would have an argument with her about that if she were still around. Not only did she not tell me that, but I had this really long two-page scene that was cut down in the movie about [Becky’s husband] Rick and how we got in the car and he hit the tree. I’m doing this whole thing, and she yells, “Cut! It was ‘a tree,’ not ‘the tree.’” So I tried it two more times so I could get as close as I could, and it’s not that I was rewriting — it was the longest speech I had ever said in a film in my career up to that point. She kept saying “Cut” when I wouldn’t get it right. So we broke for lunch and when I came back, one of the grips had taped the whole thing on his leg, away from where she could see. I sort of looked at his leg and read it. And she said, “Cut! That was perfect!” And what was perfect were the words that she wrote.
So not only could you not rewrite lines, but you had to get every “a” and “the” correct.
That is absolutely correct. When people write and direct, it’s their words. They’re connected to them. There were some performances where it was largely improvisation, like League of Their Own. The HBO one that I just did, I Know This Much Is True, we did 30 or 40 takes, some with the lines and some just made up — a different way of directing than Nora Ephron’s, which was very clear and succinct and organized.
As a former stand-up, you must like — or at least have an appreciation for — that improvisatory mode of working.
Yes, and it comes very easily to me. I loved when I got to guest-star on Larry David’s Curb Your Enthusiasm because that’s all improvisation. They just give you the basic setup and you have to make it up from there. That, I thought, was really thrilling to get to do as a stand-up comic. But not a lot of actors like improvisation. I remember when I did my first sitcom, Stand by Your Man. The pilot was with Christine Ebersole. I was getting as close to the lines as I could, and she was like, “The play’s the thing. It has to be on the page before it’s on the stage.” She’s a Broadway, Tony-winning actor. When you do plays, you’re not allowed to change the words. But somehow with TV or movies there’s more of a freedom sometimes. It depends on how the actor is trained.
Maybe Nora was being hyperbolic about the freedom she allegedly gave you. Her point was that sometimes you would slip into a Brooklyn accent instead of a Baltimore one, and she felt like maybe that was happening because the lines weren’t funny enough.
I would slip into the Brooklyn thing because that’s what I did for so many years. My act was all about that. It was difficult. It was only my second film. I hadn’t really worked that much, and I was trying to measure up to Meg and Tom.
What was your first meeting with Meg Ryan like?
It was totally like high-school girlfriends right away. We talked about our families, and we had some similar chaotic childhood stuff that we related to each other and bonded over. I loved her right away. She’s really a great woman. She’s very smart and adorable and funny and interested. The reason America fell in love with her is the same reason I fell in love with her. She’s easy to love.
My favorite scene, and maybe the most famous scene in the movie, is when the two of you are sitting on the couch lip-syncing the scene from An Affair to Remember. What do you remember about that sequence?
I remember that it was Nora’s favorite movie, An Affair to Remember. I made sure to watch it over and over. This is pre-computer times, so a VHS in your room. At the hotel, they had to hook up the machine for you. I remember watching it and watching it and thinking, I just want to get this right. I hadn’t been familiar with that movie, to tell you the truth, before I was cast.
You attended the movie premiere with Madonna, who you were good friends with at that point. Did you just call her up and say, “Come with me”?
Yep. I said, “I got a premiere for my new movie. Will you come?” She said, “Sure! Tell me when.” We went and picked her up, and my sister was there and some of my brothers. It was like a big family thing. I remember Celine Dion was there because she did the song [“When I Fall in Love”]. It was a time when no one really knew who Celine Dion was. I remember telling her how great I thought she was and her really not speaking much English. She was so kind and so fun, and I got to know her better when I had my show. We did some funny segments together, me and Celine.
I assume it was the success of Sleepless that got you the SNL hosting gig later that year?
I’m not really sure how I got that. A few years later, while I was on my talk show, Penny Marshall went on for The Preacher’s Wife with Whitney Houston. She asked me to come co-host with her because she was scared, so I went and did it twice. Listen, to be in that big movie and hold my own — it was a wonderful introduction to me as an actress after League of Their Own. It was a much subtler character, more refined, more feminine, more of a professional woman. It was a great contrast. It showed I don’t only have one type to play, and it was very helpful for me, career-wise.
Yeah, I think about the list of movies you made in the years right after that and the range of your roles: The Flintstones, Now and Then, Beautiful Girls, Harriet the Spy. What do people come up to you to talk about most often today?
It’s probably Harriet the Spy now because those kids are in their 30s or whatever. Adults stop me and say, “Oh my God, you were Golly! I loved that movie when I was a kid!” But it changes. The other week, I was on $100,000 Pyramid, which we filmed during the pandemic sometime. I went to the beach that day, and I felt like Elvis: “You were great on Pyramid!” Lately, with my hair cut short, unless I talk, people don’t always know it’s me.
Do you prefer it that way?
Listen, the wave of fame eventually hits the shore. And then it goes back out, but it’s never as strong as the first wave. People try to figure out their whole life, When is it time to get off the board and walk up to the surf and take a break? You can’t ever expect it to maintain itself, so I always had that vision of what a career trajectory was like. It never really scared me. I always knew it would have a finite beginning and end. I wasn’t looking to sustain it. I would have stayed on my TV show if I was. I wanted to spend time with my children and get to be the mother that my mother never got to be, having died at 39. I think I’ve always been lucky to have a balance of the importance of real life and the illusionary place of Hollywood.
I know that part of why you enjoyed doing the talk show was so you could be a more present parent, but by the early 2000s, you were on Broadway some, but we really didn’t see you in movies or scripted TV for a long while. Had you lost the acting bug? What kind of roles were coming your way by that point?
By the time I left my show in 2002, I was very well-known as that character. I think it would have been hard to cast me in a role in a movie. I always knew as an actress that when I got into my 60s I would be playing the Geraldine Page roles. I wasn’t going to have plastic surgery. I was going to look the way a woman my age should look, and I always thought that would be a blessing in my older age. I would get to play the Colleen Dewhurst roles. That has turned out to be true. I’m getting all this acting work now that I’m closing in on 60.
Which is incredibly refreshing. So you’re saying that people weren’t thinking of you for many roles in the 2000s?
No, and I was also pretty incendiary. I was talking about things like the war being illegal and immoral at a time when most people were not. I was talking about the problems with George Bush as a president. I was somewhat polarizing. There were some people who really enjoyed what I had to say and thought, Good for you, you speak for me. And there were other people who were repulsed by it and thought, How dare she? So once you become known for your opinions and your passions, it’s hard for people to see you as a blank canvas to blend into a character.
I assume maybe executives would have seen you as a casting risk, marketing-wise.
I don’t know about a risk, necessarily, but there were safer choices they could make. I was also home with my kids. I needed a long recovery from the six years I did [on The Rosie O’Donnell Show]. That superstardom is close to a postmortem feeling. It’s isolating and disorienting. Lucky for me, I had five children to ground me and remind me of what’s important. But make no mistake, that was a topsy-turvy time for me.
You mentioned that you and Nora ended up living in the same building. I assume you crossed paths a lot. What was your relationship like as the years went on?
It was great. She invited me into her family and took me to the Hamptons on the weekends. When I needed an apartment after I adopted Parker, she worked her magic at the Apthorp [on Manhattan’s Upper West Side]. I gave her a handful of money and she gave it to the lady with the black hair, and there you go, I had an apartment. It was a beautiful thing to live literally right above the Ephrons. Nora and I really formed a wonderful friendship, and I miss her to this day.
What a lovely thing. Were Nora and Penny Marshall friends at all?
No, I don’t think they ever met. They were almost like polar opposites.
That’s true, though they are inarguably the biggest American female directors of the ’80s and ’90s.
Yeah, but to my knowledge, they didn’t hang out or get in contact with each other. Their lifestyles were very different. Nora would throw parties with beautiful linens and table settings. She was always gathering people for a Hanukkah/Christmas party, Thanksgiving, Sunday dinners. And Penny was more of a once-a-year-with-Garry [Marshall, her brother]. She was much more into enjoying herself, not a married life raising children in New York City. They just had very different worldviews.
What is your favorite non–Sleepless Nora movie?
When Harry Met Sally, as far as the writing goes. I loved the Julia Child movie; I thought that was beautiful and touching. But Sleepless is my favorite of all her films, and I think it’s a lot of people’s favorites. It really strikes a wonderful tone, and the characters seem real. It still holds up. I just saw it about four months ago. My daughter was here, and she was like, What is this one? It would be nice if my children gave a crap about my film career, but they don’t.
So you embraced an opportunity to change that?
Yeah, I said, “It’s my second movie, Viv!” She’s like, All right, what was your first one? My son was 22 when he came home from a party and said, “Mom, when we were at John’s house, they put on this movie that you were in and you were like a teenager! You sounded like Rocky.”
Do they care about your celebrity friends? Are they fascinated that you’ve known Madonna for years and years?
No, none. There was a time when Vivvy or Chelsea would say, after Madonna left my house, “Mommy, that’s Madonna Madonna?” They couldn’t make the connection between the woman who was in my house with no makeup in her sweats to the woman they saw in public. They were like, How can that be her? “It’s really her, I’m telling you the truth.”
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