Before Anna Delvey, there were Page and Max Conners, a mother-daughter duo of man-eating, money-stealing gold diggers with thotty style. Of course, the former just got out of jail, while the latter are cult-favorite characters in one of the most playful and subversive comedies of the early aughts, 2001’s Heartbreakers. At a time when fantasy franchises like Harry Potter and The Lord of the Rings claimed the top spots at the box office, Heartbreakers was a refreshing No. 1 debut: a campy, star-studded con-medy that was equal parts rom-com, buddy comedy, and gripping crime drama. If that weren’t enough, Page, played by Jennifer Love Hewitt, had the “cool girl” confidence that the young adults the movie catered to wished they had (and the wardrobe to go with it).
Page was one of Hewitt’s first proper adult roles after years of cornering the market on playing the girl next door. In Heartbreakers, mother-daughter team Max and Page work to seduce and swindle unsuspecting rich men. During their “last con” together (before Page hits the scam market solo), plans go awry as they attempt to con a cigarette tycoon (Gene Hackman) out of his millions. Throughout their high jinks, Page is equally alluring and dripping in snark; when she isn’t using her charms on men, she’s perfectly petulant, doling out snappy comebacks that are, to this day, pure comedic gold. Sure, she is always scheming, but it’s impossible not to identify with Page’s relationship with Max (Sigourney Weaver) — one in which she just wants to have her own life apart from her mother.
In case you need a refresher, Page is neither a hero nor a villain in Heartbreakers — she’s a con artist, but one easy to empathize with because, frankly, we understand not wanting to be attached at the womb forever. Aside from the … well, grifting of it all, Hewitt plays Page as an easy-to-root-for and relatable 21-year-old rebelling against her mother; she is always prime-glam in stilettos and tube-tight dresses (whether that’s at a local tiki bar or trekking through mud during nightfall to follow a mark) and isn’t afraid of hurting your feelings. While Max is busy wedding and (almost) bedding gullible men, Page seduces them into compromising positions that make them willing to hand over some sizable divorce settlements. Two decades later, we would be honored if they scammed us (and perhaps delivered an encore of “Back in the U.S.S.R.”).
In honor of Heartbreakers’ 20th anniversary, Hewitt hopped on a call with Vulture to reminisce about how it became one of the most defining projects of her career. The actress also recalled those awkward crotch scenes with co-stars Ray Liotta and Hackman, the way the media scrutinized her body at the time, and which other stars could have played Max and Page.
What first drew you to Heartbreakers and the role of Page?
First of all, it was a chance to be in a movie with incredible actors. It was a really cool opportunity to play something that I hadn’t played before. Page was this great combination of where I was at the time: still young at heart with lots to learn, but also definitely not a teenager, and moving into her own sexuality and who she wanted to be as a woman. Having a really close relationship with my mom in real life, the mother-daughter aspect of it was appealing.
Because as much as it’s a grifting story, Heartbreakers is about a mother-daughter relationship and a mother struggling to let go.
For sure. I always loved the trust element of the story. Like a mother saying, “Don’t trust anyone, but trust me.” It is a really, really hard concept in life — who you trust — and in the con world in particular. I really love that, and, again, being able to play, on the surface, a troubled or strange mother-daughter relationship with Max and Page, but underneath it so much love.
That pink minidress that you wear when you bust into Jack’s bar is iconic. Did you end up keeping it?
When I walked in for my first fitting, I thought all the dresses were tops and didn’t know where the bottoms were. I remember watching them unpack some of my things, and they were in ziplock bags, and I was like, “My clothes … are in there?” And we all had a really big laugh about the fact that I just wore tiny clothes the whole movie. I felt like a Barbie doll. It was great.
I think I did keep it for a short period of time. Then, usually what I would do with things that I got to keep from movies is I would give them to my best friend, Jenny, so it wouldn’t surprise me if that dress is still somewhere in Indiana, where she lives, in her closet.
Because your costumes were more revealing, I heard you had someone who had to monitor if your clothing was like riding up too much. Is that something that would normally happen on a set?
I think so. It’s such a physical movie. I mean, she was constantly tripping and falling down. One thing that really stood out to me when we did the movie is how much people were looking out for me and really making sure that I never felt weird or on display. I remember there were more than a couple of people that were like, “Okay, let’s make sure boobs are in place and we’re not seeing underwear.” I remember, one of my very first days of work, being attached to Ray’s nether regions for eight hours, so it was a very risqué part for me at the time.
Wait, that Ray Liotta crotch scene [where your hair is caught in his zipper] — you filmed that on one of your first days on set?
It was very, very daunting for me — not because of what I was doing in the scene but because I was aware of who he was. I was such a big fan. I was so nervous to mess it up. I just remember meeting Ray, and instantly I felt so much better. He was the kindest, funniest, sweetest man who made me feel so comfortable. I was young, so my mom was with me most days on set, and that day, I just remember the very first shot, I was bent over. I remember hearing my mom go, “Oh goodness.” I asked her afterward, “What was the ‘Oh goodness’ for?” She was like, “It’s just your butt. It’s just going to be your butt, giant on the screen.”
People thought that I was more ready to play Page in how comfortable she is in her sexuality in the movie than I really was. I was very young, and I think people thought that I was more that person because I did Maxim covers. There were lots of conversations between David [Mirkin, the director] and I where he’d be like, “Page is feeling a little bit sexier this time,” and I would be like, “How do I pull that off?” We had such funny moments where he was like, “Okay, now I’m going to be a grown man who’s going to try to show a very young girl how to be sexy as a woman.”
Was your hair really stuck in Ray’s zipper?
Yes, they picked one piece. I had extensions partially in my hair, but I was there for a very long period of time. My next scene was with Gene Hackman — one of the only ones that I have with him in the movie — and I wiped water off of his crotch. When I look back, it’s like … what a weird job.
Your grandma was also there watching you film that scene with Ray — and his crotch. How did that go over?
It was the perfect day to bring your fam. I don’t really know why I did that, except that they were the two biggest female influences in my life. I wanted to feel comfortable. There was a part of me, also, that wanted them to feel comfortable with what I was going to be doing, and I knew if I can do this scene in front of my mom and my grandmother and they’re cool with it, the rest of the movie is gonna be just fine. Because it was really the most provocative thing that I had done at that moment besides a [Maxim] photo shoot. My grandmother thought it was hilarious.
There are so many icons in Heartbreakers — obviously Sigourney, Ray, and Gene but also Jason Lee, Sarah Silverman, Zach Galifianakis, Carrie Fisher, and Anne Bancroft. Was it daunting to act alongside them?
I always felt like I was like the random person who won the radio contest to do a part in a big movie. Every time I looked around, there was this amazing person that I was getting to work with, even if it was only me and their crotch.
How much of the movie did you spend making out with Jason versus acting with him?
A lot of the movie. We had such a good time. Jason and I were just constantly making out. It was hilarious.
One of my favorite mother-daughter moments in the movie is when Max ropes Page into a spontaneous con by tripping her in a hotel lobby. Did you really trip?
Yes. She did really have to trip me. She did it gently and then it was kind of up to me to do the rest. But I broke my fingers and then couldn’t do too many more takes.
But you got to get Max back later by attacking Sigourney in a car.
It was terrifying because you’re like, “Oh my gosh, I’m not gonna do this to Sigourney Weaver.” She was great about it, and it was really fun. The person that I actually hurt the worst in the movie was Ray, because I actually punched him in the face. He was sweet about it. I hadn’t really done a lot of that stuff before, and they moved his mark closer in between takes without necessarily telling me.
With socialite grifters like Anna Delvey — and general con stories — becoming catnip to pop culture, do you feel like there’s a newfound relevance to the movie?
I do. At the time that we made that movie, that wasn’t really the case. The con world is really interesting; so many con artists are really smart. It’s been really fun for me to see how many lives Heartbreakers has. It’s still the top-three things people talk to me about.
Did you study any con artists in particular when you were preparing for Page?
[The crew] had us meet with one former con artist [and] a magician to do the card tricks to show how fast you have to be. They shared with us a couple of videos of card tricks and somebody explaining how the glass trick works that we do in that restaurant. Sigourney and I felt like ballers.
In rereading interviews with you around the time of the movie, there was so much leering in the media about your body. How do you look back on those conversations and discussions?
It’s interesting, I just watched the Britney Spears documentary [Framing Britney Spears], and there’s that whole section in there talking about her breasts. At the time that I was going through it, and interviewers were asking what now would be incredibly inappropriate, gross things, it didn’t feel that way. I mean, I was in barely any clothing the whole movie. For some reason, in my brain, I was able to just go, Okay, well, I guess they wouldn’t be asking if it was inappropriate.
But now, as a 42-year-old woman with a daughter, I definitely look back on it and go, Ew. And it really started with I Know What You Did Last Summer, because that was the first time that I had worn a low top, and on Party of Five, my body was very covered. At a press junket for I Know or I Still Know What You Did Last Summer, I remember purposely wearing a T-shirt that said “Silicone Free” on it because I was so annoyed, and I knew something about boobs was gonna be the first question out of [reporters’] mouths. I was really tired of that conversation. With Heartbreakers, that was a big part of it. I was disappointed that it was all about body stuff, because I had really worked hard in that movie to do a good job as an actress. So I remember one specific moment wishing that the acting had overshadowed all that — that for five minutes, they had said I was really great in the movie versus made a body comment. Now that I’m older, I think, Gosh, I wish that I had known how inappropriate that was so I could have defended myself somehow or just not answered those questions. I laughed it off a lot of the time, and I wish maybe I hadn’t.
You were so young at the time. People were talking about your breasts and your body before you were even 18, and you were dubbed a sex symbol.
The conversation for a very long time in my career was always about [my body] first — then, “Oh yeah, you were really great in the movie, too,” later. I didn’t get it. That’s just what I looked like, and I was doing my job. I just started to [prepare myself], like, I know I’m doing an interview today, so I’m pretty sure at least 20 of the 40 minutes is going to be about boobs and body stuff, so we’ll just get that out of the way and then maybe they’ll ask me something else. When I watched that Britney Spears documentary, it hurt my heart a little bit, because I remember in hindsight having that feeling. I’m really grateful that we’re in a time where, hopefully, that narrative is going to change for young girls who are coming up now, and they won’t have to have those conversations.
Obviously, you and Sigourney were a stellar pairing in Heartbreakers, but do you know who else was considered for the roles of Max and Page?
At one point, they talked about Cher and Cameron Diaz, which I think would have been really cool. They talked about Jamie Lee Curtis at one point. I want to say Christina Ricci’s name came up. I think it was Christina Ricci and Anjelica Huston, which also would have been amazing. I still don’t know why they settled on me and Sigourney, but I’m so glad that they did.
Was there ever talk of a Heartbreakers sequel? Where would Max and Page be now?
There was talk of a sequel, but it’s really been in the last five years — what that would look like, if Page would be back in the game, and if Max would still be in it. I’ve always been really open to doing that and exploring that, but it just never happened. It would be interesting to see how much Page turned out like her mother. That would be her worst nightmare, but it’s inevitable. It’d be interesting to see where their relationship is and the effects of being con women for that long period of time. I’m in my 40s, so I’m not going to do [Page’s] wardrobe again right now.
If there wasn’t a sequel but a reboot, who do you think would be a great Max and Page?
I know exactly who I think would be great: Jennifer Lopez and Jenna Ortega. They would be the perfect Max and Page ever. I mean, Jennifer Lopez — we don’t even have to explain that because she’s perfection. But Jenna reminds me so much of where I was at that time. She’s so beautiful, and she has this innate adult thing about her, but she’s a kid.
Were there any types of projects you wanted to take on during the Heartbreakers era that you didn’t get to?
I always feel very fortunate for the stuff that I got to be in. Honestly, I was always shocked, as I’m sure other people were, that I got cast in some of these great movies that I got cast in. The one thing that I still haven’t really gotten to do is that sort of great rom-com niche that’s out there. Even though parts of Heartbreakers were considered a rom-com, and I guess my part in Can’t Hardly Wait was sort of rom-comish, I just never really got to do that Julia Roberts My Best Friend’s Wedding kind of vibe. Now that I’m in my 40s, I’m like, Okay, where is it? It’s got to be out there somewhere. So that’s still something that I really want to do and I’m constantly looking for. I have faith that one day I will find the right rom-com or it will find me.