YMMV / Heartbreakers

• Adorkable: Dean and his Sickeningly Sweethearts way of trying to win Max back - singing "Come Fly With Me" on his knees in a hotel lobby. Who knew that Ray Liotta could be so adorably dorky?
• Best Known for the Fanservice: This movie is primarily known for Jennifer Love Hewitt walking around in very flattering dresses, with Roger Ebert calling the movie a walking commercial for the Wonderbra. On a different level, those who had a thing for Sigourney Weaver could finally see her getting a Lingerie Scene.
• Big-Lipped Alligator Moment: Involving an actual alligator; a random shot of an alligator eating a duck is inserted as Max and Paige drive to Palm Beach.
• Crack Pairing: The raison d'etre of the two women, so there's some of this in-universe. But Sigourney Weaver and Gene Hackman probably takes the cake. And although it doesn't happen in the movie, the implication of Hackman with Jennifer Love Hewitt is there too.
• Crosses the Line Twice:
  • A man dying is tragic. A man dying by hitting his head off a statue's penis, while he has an erection himself? Funny. Max trying CPR, only to get repulsed by the cigarette smoke still in his mouth? Hilarious. Having to hide the body on a balcony and it then falling down several storeys? HYSTERICAL.
  • Tensy casually talks about his company testing cigarettes on nine-year-old children.
  "After a few hours of puking, you couldn't get them away from the stuff."
• Designated Villain: Technically Ms Maddress is only a villain in the sense that she's opposed to Max's con. She's an Asshole Victim but only because she's specifically hoping for a payout when Tensy dies.
• Do Not Do This Cool Thing: Sigourney Weaver herself said she was tempted to try out some of the cons Max and Paige resort to.
  • Pouring glass fragments onto a plate to get a free meal.
  • Tripping Paige on a hotel lobby, and then squirting water to make it look like she slipped to get a free room.
  • Distracting a man paying for gas by asking for directions so that Paige can briefly swipe his credit card.
• Ensemble Dark Horse: Dean gets the best lines, and Ray Liotta is clearly having a ball pretending to be Paige's 'cousin Vinny'.
• Crowning Moment Of Funny:
  • Jack's first scene - he comes over to Paige in the bar and asks her if she wants a drink. She assumes he's hitting on her and goes off on a tirade about how he doesn't know her but just wants to get with her only for him to say he's the bartender.
  • The car crash scene. Paige lays spikes on the road for Tensy's tyres to burst on...but she accidentally gets Jack's car (as he'd followed her to return her purse). To get him out of the way, she pushes him down the hill and tries to pretend her ankle's hurt. Then to distract him even further, she starts making out with him. And as soon as the others are gone, she screams "get off me!" as if she hadn't initiated the kiss and runs off. This distraction also means she can't remove the spikes, and Max's tyres get popped too. She improvises by driving Tensy to hospital anyway, sparks on the road and all.
  • Bilingual Backfire kicks in when Tensy takes Max-as-Olga to a Russian restaurant. She has to pretend she understands the orders in Russian, and ends up ordering steak tartar.
  • How the Conners get Ms Maddress out of the way. Max plants the cigarette lighter Tensy gave her in yesterday's dress. When Tensy wonders if Ms Maddress is telling the truth, Max turns on the tears and collapses on the housekeeper's pillow. Upon wondering why the pillow is so hard, she 'uncovers' some of his previous wife's jewellery. Ms Maddress knows she's being set up and charges at Max, who then shields herself with the wardrobe door...and revealing the last part of the play: stacks of Tensy's cigarettes. It's that of course that has him call the police on her, also slipping the officer a bit of cash saying...
  "If it's possible, could you slap her around a little?"
  • Dean randomly shooting fish in the sea.
  • Max's Heel Realization...
  Max: I'm a terrible mother. I'm a terrible everything!
  Paige sits down next to her, puts an arm on her shoulder, looks like she's about to comfort her and...
  Paige: You're finally seeing things clearly.
• Crowning Moment Of Heartwarming:
  • Paige arrives late to the game she was going to with Jack, the bar seemingly empty with everyone gone. But Jack is waiting there, ready to tell Paige this.
  Jack: My friends have this theory that...I'm in love with you...
  • Paige's reaction to the above is to look stunned, as if not believing that someone could love her, and getting a Big Damn Kiss. Even Max watching from binoculars could tell she was in love for real.
  • Paige is willing to con Jack to pay off Dean, but immediately backs off when she realises what losing the bar would mean to him. Max likewise wants to call it off when she realises how she may be hurting her daughter.
  • Max completely melts when she sees Paige in her wedding dress.
  • It's also quite sweet when Max and Dean get together for real.
  • The sweet part of the Bittersweet Ending. Jack returns to the bar to find it being opened back up again by his friends, with a "welcome home Jack" sign, and Paige handing over all the paperwork. She then tells him her real name, showing she's learned from the events and is willing to face the consequences of her actions.
• Hollywood Homely: Paige views Dean as an Abhorrent Admirer and says her mother is in "serious denial" when Max says he was cute. She might have been talking about his personality, but you'd think Ray Liotta was a hunchbacked Gonk by the way she goes on.
• Jerkass Woobie:
  • Paige is quite nasty, but you have to feel sorry for a girl who's been raised by her mother to act as a conwoman so they can make their money. Paige's devastated look when she discovers Jack in bed with her mother is a huge Tear Jerker.
  • It's not drawn attention to, but Max was abandoned by a previous lover and ended up alone and pregnant, except for Barbara - and since she has no problem screwing Max as well, that can't be called a true friendship. While she makes her money conning rich assholes and is a smothering mother, she admits that she doesn't want Paige to get hurt the way she did. It's not hard to feel a little sorry for her when she has her Heel Realization.
  "I'm a terrible mother. I'm a terrible everything!"
• Narm Charm: Sigourney Weaver singing "Back in the USSR" in a ridiculously fake Russian accent - and it's awesome.
• Retroactive Recognition: Zach Galifianakis has a minor part as one of Jack's friends at the bar (along with Sarah Silverman), 8 years before his breakout role in The Hangover.
• She Really Can Act: Jennifer Love Hewitt at this point was best remembered for the melodramatic Party of Five or else Teen Idol roles like I Know What You Did Last Summer (where fans infamously hated that her character was the protagonist). Here, she shows that she could go against type to be a rotten person with a lot of depth, have some killer comic timing and hold her own against the likes of Sigourney Weaver and Ray Liotta.
• Tearjerker: The look on Paige's face when she finds Jack in bed with Max is enough to set anyone off. But it gets better.
• Stoic Woobie: Jack gets put through the ringer in terms of his mixed messages from Paige, and his friends even think he's being messed around with. Then he gets drugged by Max, nearly sexually assaulted on his wedding night, with his wife divorcing him and taking the bar that belonged to his dad. Despite this, he never complains once. Mercifully, he catches a break at the end.
• Values Resonance:
  • In Paige's tirade when Jack first asks her if she would like a drink, she drops the phrase 'the male penis'. At the time, this would have come across as redundant and was likely written to highlight her Straw Feminist tendencies, but as gender theory has expanded and trans rights have become more of a talking point in the new 20s, many people might recognize that there is in fact a difference between the male and female penis and appreciate Paige's specificity.
  • Max's Moral Event Horizon in the movie is drugging Jack to make it look like he slept with her willingly. Subverting the Double Standard regarding sexual assault of men remains very relevant today and while Max does get forgiven, we can hand wave that with the fact that she didn't actually sleep with him and likely wouldn't have if the intent was just to trick Paige. She does get read the riot act by both Dean and Paige, and she has to earn her redemption by getting Paige to go back to Jack.

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