Sometimes, a poster tells you everything you need to know about a movie. In the case of Heartbreakers, which turns twenty this month, the designers are advertising a different film entirely. Gene Hackman, red-nosed and gurning, leers at Sigourney Weaver and Jennifer Love Hewitt, who are wrapped in caution tape warning of “dangerous curves ahead” – get it? ‘Cause they’re sexy ladies (insert honk-honk noise here). 

On paper, the premise is borderline offensive; a mother-daughter duo scams gullible men out of their money by marrying and then ditching them, typically after implicating the dude in question in infidelity to ensure his ex-wife gets everything. Happily, despite the fact Heartbreakers was directed by a man (David Wirkin) from a script written by three others (Robert Dunn, Paul Guay and Stephen Mazur) – none of whom have done much in the intervening years, curiously – the movie is unabashedly on the side of its female protagonists. It’s a giddily remorseless romp in which the devious duo, crucially, are never punished for their actions. 

In fact, considering the luxurious Palm Beach setting, where most of the action takes place, this is damn near wish fulfillment.

Heartbreakers’ ensemble cast is top notch – unsurprisingly, two women (Juel Bestrop and Jeanne McCarthy) chose it – with Hewitt and Weaver perfectly matched as the scheming Page and Max, respectively. Hewitt was 22 when the film was released, in 2001, and Weaver was 52. While their age difference doesn’t chime with the idea Mom got pregnant young and became a con artist to make ends meet, it allows the necessary room for both actresses to shine in stunning, age-appropriate clothing. In fact, Weaver’s outfits were so key the legendary Ann Roth handled them personally. Adding an extra wow factor, none other than Mrs. Robinson herself, the late Anne Bancroft, features briefly as Max’s mentor, and she too is dressed beautifully.

The male stars are impressively varied, even strange choices, with Ray Liotta taking on a softer role than usual as Max’s latest victim, Dean. Liotta retains some of his Goodfellas edge at least, pulling out a knife to rip off his new bride’s purposely restrictive lingerie. Early on, a wonderful sight gag sees a horned-up Dean running down a seemingly endless hallway with Max in his arms, which is representative of how the film makes fools of its men. In a subsequent effort to win her back, the Jersey schmoozer publicly sings Sinatra’s “Come Fly With Me” (Weaver one-ups Liotta by performing a Beatles track onstage in a purposely bad Russian accent). Max and Page don’t even pay for gas, they’re that good. The film’s raunchiness, meanwhile, comes predominantly from penis humour despite the amount of cleavage on show. 

The Connors, which is their actual surname believe it or not, only mess with women to get even. Ladies occasionally spoil their plans, but Max and Page tend to come out on top regardless of the situation. Even when things go wrong for them, they somehow end up going right. Take Page’s attempts to prove that she’s a pro in her own right, which lead to a meet-cute with Jason Lee’s bartender, Jack, and a feminist rant that culminates with him telling her, very plainly, that he’s asked for her drink order only because it’s his job. Also, the Heimlich manoeuvre is administered and several cars crash into each other because of Page’s negligence. Heartbreakers is wacky, even screwball, at times like when Max gives Hackman’s despicable Tensy mouth to mouth and then exhales smoke immediately after.

The disgusting, and disgustingly rich, owner of a tobacco company who holds the key to setting the gals up for life, Tensy preaches the benefits of getting kids hooked on cigarettes as soon as physically possible. He is a horrifying creation that the Oscar winner plays with ruthless aplomb, whether stubbing a cigarette out in someone’s glass of wine, Tensy muttering “Nazi” as he does so, or openly smoking in hospital. Hackman is terrific, completing a trio of vastly different performances from the male leads, who exist primarily so Hewitt and Weaver shine brighter.  

Even Jack, the sole decent male character, proves a fascinating foil for the foul-mouthed and acerbic Page, a woman used to fighting first and asking questions later. Lee is a terrific choice since, prior to Heartbreakers, he was known predominantly for playing slackers in Kevin Smith movies – compare Jack to Mallrats’ odious man-child Brodie, who manages to pull Shannen Doherty by sheer force of will. Jack isn’t perfect but he’s comfortable with his lot in life and, more to the point, the schlubby bartender introduces Page to the idea of having fun for free rather than constantly chasing the high of the next scam. Jack’s friends and colleagues are played by a then-unknown Zach Galifianakis and Sarah Silverman, too, which adds a whole other layer of charming weirdness to the casting.

Max and Page are an unconventional odd couple and the movie’s real love story is theirs, even though the two spend most of their time bickering – Page is incensed at the suggestion she’s been nice to her Mom, while Max consistently picks apart her daughter’s outfit choices, finally acquiescing and telling her sweetly, “wear whatever you want…except what you’re wearing.” The devilish protagonists are exceedingly well-drawn, Max the clear alpha who refuses to admit her own daughter might be a better lure for men than she is, while Page’s foibles – her reckless driving, card tricks, and smoking out of the corner of her mouth – establish the younger woman as a total wildcard. Page’s romance with Jack is sweetly believable since he’s quite literally the only nice man she has ever come across. Weaver and Hewitt are well matched, both gifted physical comedians who snipe at each other to endlessly entertaining effect. The actresses were at completely opposing points in their careers, but their pairing here is ingenious.

Heartbreakers revolves around one final, big con that will set Page up on her own but, in reality, Max has conned Page to stop her from doing exactly that. Over the course of the movie, several references are made to other con jobs, including one which requires a trumpet and a parrot, adding to the greater impression of the colourful, aspirational world these women inhabit. And yet, a sewing machine stashed in their hotel room coupled with a shot of Max hand-stitching a dress Page was wearing earlier in the movie suggests they’re practically savvy as well as financially. Life skills come in many different forms and, although Max’s parental lessons are more than a little dodgy, there’s no doubt Page can handle herself in virtually any situation.

Heartbreakers is decadently shot, ice cream sundaes given as much love from the camera as the sexy but age-appropriate outfits, while John Debney’s score utilises Spanish guitars for that luxury holiday vibe. The film’s theme, meanwhile, is an earworm concocted by none other than Danny Elfman. During Page’s initial seduction of Dean, the camera is trained on her cleavage – in an appreciative, rather than leering manner – while danger music, the kind now prevalent in reality TV in fact, alerts us to the impending threat she poses. DOP Dean Semler shoots everything in Palm Beach with a sunny glow, while New Jersey, where the story begins, is dull, grey, and lifeless, the implication being Max and Page belong among the colours.  

Each potentially saccharine moment is undercut with sharp humour, particularly as mother and daughter gradually thaw towards each other. And, although the movie is certainly romantic, there are no sex scenes or nudity whatsoever, which distinguishes it from the smutty comedies that were inexplicably popular in the late nineties/early 2000s. Heartbreakers’ edges were reportedly sanded down so the film could achieve an R rating, but there’s nothing to suggest the outrageousness has been scaled back. If anything, the filmmakers get away with more than you’d expect given the subject matter.

Although the film likely wouldn’t pass the Bechdel Test, since the conversations tend to revolve around the men being scammed, there’s an argument to be made for Heartbreakers as a modern feminist text. After all, it’s about two women making their own way in life no matter what it takes — one of whom is a single mother. And, in stark contrast to darker fare such as Netflix’s recent I Care A Lot, the central duo doesn’t get their comeuppance or even learn the error of their ways. Heartbreakers is fun, flashy and frequently laugh-out-loud hilarious but, underneath it all, this is a story about a mother and daughter realizing they can only really depend on each other. Besides, Carrie Fisher cameos as a cutthroat lawyer. Case closed.

Putting paid to the adage that Ginger Rogers did everything “backwards in heels,” there isn’t an activity these two ladies partake in without stilettos – “Those shoes… are so wrong for this” Mom quips en route to a bank meeting – and, when Dean threatens to rat them out to the cops, he emphasises how they’ll be sent to a filthy prison “with bad lighting.” In one of the movie’s funniest moments, which understandably featured prominently in the trailer, Max demands Page feel her butt, to which the unimpressed twenty-something responds, “I’m not going to feel your butt again mother, we all know it’s wonderful.” Weaver somehow looks even more gorgeous than Hewitt, although she’s thirty years her senior, which feels progressive, even nowadays.

Max and Page notably aren’t punished for caring about how they look. They don’t endure a make-under or have to crawl through the mud to be exonerated – though Page does, literally, get stuck in the mud at one point, but she’s still dressed to the nines, so it doesn’t count. It’s kind of depressing that a movie from twenty years ago feels so special simply because it allows women to be shamelessly sexy, ruthless, and conniving without demanding they atone for their sins or change completely to hook “good” men who’ll keep them on the straight and narrow. Underneath all the beautiful clothes, fast cars and juicy schemes, Heartbreakers is about trusting your gut and knowing that no matter what life throws at you, or how society is structured to keep you down, there’s always a way out. And it usually involves a really good wig and a really bad accent.

by Joey Keogh

Joey Keogh is a freelance writer from Dublin, Ireland with an unhealthy appetite for horror movies and Judge Judy. In stark contrast with every other Irish person ever, she’s straight edge. Her favourite movies include 10 Things I Hate About You and Scream, but defending Queen of the Damned is fast becoming her vocation. She tweets, mostly about “feminism and hating Ed Sheeran,” according to her little sister, at @JoeyLDG. Hello to Jason Isaacs.