Boy, that
Severance finale was good, eh? With all the acclaim and accolades he's receiving these days as a director/producer, it's a real possibility at this point we never see Ben Stiller starring in a comedy film again. Which, ya know, is and isn't a shame.
Stiller certainly has a unique energy for someone who ended up an A-lister. His first big break (outside of a small role in Spielberg's war epic Empire of the Sun) was being hired as a writer and performer on Saturday Night Live, where he left after only 4 episodes because they wouldn't let him do his more esoteric short films. Later on, he'd land his own sketch show at FOX, where he cast Janeanne Garofalo, Bob Odenkirk and a totally chill guy named Andy Dick as his co-leads, and filled his writers room with the likes of future Mr. Show vets David Cross and Dino Stamatopoulos. That doesn't read like a guy who'd eventually headline three Night at the Museum movies.
Pictured: A man more than likely saying "goddamnit!"
But that was the interesting thing about Stiller as a star. More than most, you could feel the "one for them, one for me" energy at play in his works. There's a palpable joy he has when he gets to bite into a more zany, off-beat or even off-putting character that stood further in contrast the bigger he got to the increasing lifelessness he'd bring to every Focker and Museum sequel.
A still from Night At the Museum 3, a movie featuring Robin Williams' final live action performance. Yep...
The Heartbreak Kid, released in 2007, comes at an especially interesting moment in the Stiller timeline. His most recent films at this point are Meet the Fockers, Madagascar, and Night at the Museum. All three are huge hits. At this point in time, Stiller has nothing to worry about in terms of losing his box office draw. What does he have to worry about? Looking fucking lame. Those films are all incredibly safe moves, and it's clear to see why they made money, but none of them are going to make you cool or interesting to the younger comedy fans who were once Ben's bigger boosters, back in the MTV and FOX days.
Ben Stiller, just absolutely loving this...
You know what is cool with the kids at this time? The Apatow sensibility. Oh yea, we're right in the thick of Apatow and his buddies taking over in Hollywood. In 2007 alone, Judd directs Knocked Up, produces Superbad, and co-writes the underrated gem (at least at time, its got its flowers at this point) Walk Hard. Now, remember all those names I listed a second ago of people who worked on Ben's FOX show? There was one I left off. And that's -- guess who? Ol' "he could have killed him" Judd Apatow himself! So obviously the logical move for Ben at this point, looking to regain some cool points was to....relink with the Farrelly Brothers.
Peter Farrelly, a man who won Best Picture (somehow), but whose true passion project was a mid Stooges movie.
Now on one hand, that's a move that makes sense. One of Ben's biggest ever hits was with the Farrellys: There's Something About Mary. Now that's a movie that led to the Farrelly's style of comedy being the hot new thing for a number of years. Gross out humor had existed long before, but there's a way that movie pulls off the nastiest shit and manages to still land as vaguely sweet that just shot it through the stratosphere at the time. Like, my mom loves that movie, and its most famous joke is about Cameron Diaz rubbing a load through her hair! American Pie came in the next year and hit the exact same alchemy, and suddenly the trend was set: we want it gross! We want Tom Green to play a major role in Road Trip! We want Anna Faris to get fucked so hard that turbo jizz shoots her to the ceiling in Scary Movie! We want Austin Powers to drink a pot of shit, and then complain that it tastes a little nutty!
The cum joke that crushed in malls all over America
But by 2007, not only had the Farrelly imitators fallen off, the Farrellys themselves weren't looking too hot. Their initial run of 90's comedies (Dumb and Dumber, Kingpin, There's Something About Mary) aren't high art, but in terms of sheer dumb laughs, they're pretty undeniable. Following the success of Mary, they relink with Carrey for Me, Myself and Irene, which isn't bad but does already feel like they're chasing themselves. Everything is just amped up to a 10 and feels a little too desperate to shock. In 2001 they pulled a Spielberg and directed two films in one year: Shallow Hal, a movie people liked only OK then and have gone on to like even less with time, and Osmosis Jones, a live-action/animation hybrid where they handled the live action portions. Guess which parts of the movie people hate?
The role Bill Murray reflects on when he wants to look back positively on the Garfield movies by comparison....
...And the role Gwyneth Paltrow doesn't reflect on, period.
Following that, they released the conjoined twins comedy Stuck on You and the Jimmy Fallon starring Red Sox romcom Fever Pitch. These films, as well as Shallow Hal, saw them abandon the full-on in your face raunch of Mary and Irene in favor of making the films PG-13 and shooting for a wider audience. All 3 films made less than either Mary or Irene. So for the Farrellys, going back to a hard R rating and re-teaming with Stiller made a lot of sense. But what attracted Stiller to come back? Again, he had the connection to Judd, having even starred in his Judd's first feature, Heavyweights, way back in the 90's.
Ben Stiller, Judd Apatow & Kenan Thompson all collaborating at a time when no one would care (and they did not!)
Perhaps Ben was just such a big fan of the original Elaine May classic that doing a remake intrigued him. The only problem with that theory though is that this movie fundamentally misunderstands the original Heartbreak Kid. That film has a seething hatred for its male protagonist, a man who falls in love with a beautiful young (emphasis on young) woman on the first day of his honeymoon. His wife is eccentric, sure, but the humor is entirely coming from it being a comedy of errors this guy has forced himself into. All he needed to do to avoid the headaches he's causing himself throughout the movie was just not try to fuck a teenager on his honeymoon.
Charles Grodin as the ultimate "this fucking guy"
Much has also been written, by people far more qualified to talk on this than me, about the original's film Jewish identity. It is explicitly a film about Grodin, a Jewish man, leaving Jeannie Berlin, his Jewish wife, for Cybill Shepard, a young blond WASP. May even specifically shut down Neil Simon (who wrote the film)'s suggestion of Diane Keaton for the Shepard role for not being enough of a "shiksa". Note that in the remake, Ben instead leaves the beautiful blonde Malin Akerman for the brunette "nice girl" Michelle Monaghan, meaning we fully lose that thread of commentary.
Still, perhaps this sort of self-hating Jew and all around self-pitying person that the audiences loves to hate appealed to Stiller. Unfortunately, that's not the guy he plays in this remake. I mean, it is, but the key difference is that the movie doesn't believe he is. Which, of course it doesn't. The Farrellys always write lovable scamps who, sure, maybe have some character flaw they have to overcome, but are at the end of the day guys you want to root for. You want Ben Stiller to win Cameron Diaz's heart in Mary; you want to see the Kingpin guys win the tournament; and, sure, you may know Lloyd won't get the romance of his dreams he's hoping for in Dumb and Dumber, but you still want those guys to get through everything ok and come through it all as cluelessly happy as ever.
I don't have a funny caption for this one, but hey, isn't Dumb and Dumber fun?
That type of role is also Stiller's bread and butter. His mode as a movie star was essentially "normal guy reacting to craziness"; a slightly more sarcastic Mikey Day. Yet you can feel him relish the times he's gotten to play full asshole, such as in
Dodgeball or
Happy Gilmore. Even when he's done little cameos on shows like
Extras and
Friends,
that's the mode he chooses to deploy over his more typical nice guy shtick. Now, theses are all professionals, so there's never been any public indication of this, but I get the sense there was some fundamental miscommunication on this project between what actor and director wanted. Because it feels like, after a string of dependable-but-safe hits, this was Stiller wanting to dig into something a little nastier and perhaps even weaponizing his star persona a bit. Which is a movie that might have been interesting. Instead, what the Farrellys wanted to do was have Stiller play another 'nice guy' in a raunch fest that only challenges the audience with how much Carlos Mencia they can take.
Another ultimate "this fucking guy"
It's also unclear what film the studio wanted here.
The Heartbreak Kid was one of many Neil Simon penned hits of the 70's, but that was at a time where these sorts of wry, character based comedies were more in fashion with the general public. That was very much not the type of comedy in vogue in the 2000's. Still, that's not to say there weren't exceptions, with movies like
Sideways and
Little Miss Sunshine raking in major bucks on indie budgets. But did they get Alexander Payne or Noah Baumbach to write the script? No. Who did they reach out to first?
Entourage creator Doug Ellin.
Good ol' Vinny C and the boys from Queen Boulevard taking Hollywood by storm.
Now, to be fair, the studios had been trying to remake this film since the 90's, so Ellin was reached out to write & direct (oh yeah, they wanted double duty) far before he showed us the zen ways of Johnny Drama and Turtle. But he still seems like a guy who, even in basic pitch meetings, is going to present the exact wrong energy to remake a film from Elaine friggin' May.
Either way, the Ellin script didn't work out, and the idea of remaking the film sat on the bench for another 5 years, until 2003 when Scott Armstrong, fresh off of writing Old School, and Leslie Dixon, fresh off of writing the Freaky Friday remake, were hired to write a new script for a Heartbreak remake. This one gets even further along in development, with Men In Black's Barry Sonnenfeld attached to direct and Jason Bateman and Amy Poehler attached to star. Still, this ultimately doesn't go ahead. And that's when the script makes its way to the Farrellys, still in the midst of their decade plus pursuit to get a Three Stooges film made (and boy was the final product worth all the effort!) That was the Farrelly's passion project, a film at one point set to star Jim Carrey, Sean Penn & Benicio Del Toro, and that ended up starring Sean Hayes, Chris Diamantopoulos & MADtv's Will Sasso. The Heartbreak Kid, on the other hand, feels like a safe move to make in the mean time. "Why don't we keep doing that thing we're known for, and get back to doing the raunchier version of it?"

We all remember that beloved sequence where Moe joins the cast of Jersey Shore
So that's my best guess at how the Farrellys got attached to this. I'm still a little more confused on why Stiller chose this particular script though, at a moment where he was one of the most popular comic actors working. Maybe Stiller just really respected the work of Nichols and May, considering his own parents are also a beloved comedy duo. And this is certainly a movie that respects those kinds of important figures in comedy history, which is why it begins with Jerry Stiller himself asking his son "you been crushing any pussy?" This is among many wonderful Jerry lines in this - who plays the irascible, crude father of Ben's character - including, because it's 2007, "bitches be crazy".
Jerry Stiller, enjoying himself (and yes, I'm censoring the Kind way)
If you haven't picked up on it yet, this movie's biggest flaw in comparison to the original is just how bro-y it comes off. Which, hey. I like some fratty stuff from the 00's, even if it hasn't aged the best. Superbad is still hilarious. I'll always adore the Jackass films. Hell, I even generally enjoy the ultimate frat flick, Old School, which, again, has the same writer as this film. So it's not even that I inherently hate that approach as much as it just being an entirely wrongheaded one for tackling this film. In changing the vibes in that particular way, the entire point of the original gets lost. No longer is the film about a schmuck who blows up his life because he wants a hot young piece of tail, it's about a nice guy who got tricked by some evil bitch into believing she's the one, only for him to meet someone who's actually way more chill and totally one of the guys. It takes the gleeful nastiness of the original film and replaces it with a much uglier kind of nasty.
The evil bitch in question is Lila, played by Malin Akerman, who, God bless her, at least tries to have fun with the role. It's not like you can't have fun with the premise of "dream girl turns out to be nightmare". But this doesn't even clear the low bar of other movies with that premise like The Wrong Missy or Mike and Dave Need Wedding Dates. You can have a lot of fun with the ways the movie slowly reveals her awfulness, yet they don't really choose to. She just becomes more unpleasant, and starts revealing dark backstory details like a cocaine addiction that's led to a deviated septum. The original Jeannie Berlin performance is so impactful she received an Academy Award nomination for it. No matter how hard she tries, Malin's not winning any awards for getting fucked by a donkey. Which, yes, is the post credits scene.
They have sex off screen and then show you this after, in case it was too subtle
That's not the movies only off-putting sex scene, as we also get treated to an extended scene of Malin writhing around and riding Stiller while yelling such phrases as "cock me!" and "fuck me like a black guy!" As well as her calling him the F-slur for not wanting to hit her during sex. We then cut to the next morning, where Ben is cowering in fear on a chair as Malin sleeps peacefully. It's like someone took the scene in
Wedding Crashers where Isla Fischer rapes Vince Vaughn and went "I want the version that makes audiences even in the mid 00's feel uncomfortable."
See how the donkey scene is a callback? An awful, awful callback...
So now we know the personality of the girl Ben wants to leave. But what about the girl he wants to leave his would-be-wife for? Well, that character is Miranda, played by Michelle Monaghan (recently of
The White Lotus S3 -- another role she got a free vacation out of, though likely one she's ultimately much more proud of), and her personality is "female comedy lead". She's chill, she'll joke around (without being
too funny), she has seemingly nothing wrong with her other than -- uh oh, can you say contrived? -- she's
also in a relationship. And wouldn't you know it, this guy kinda sucks too? It's almost like we should root for these two crazy kids to run off together.
One of the many electrifying and totally not rote scenes between Stiller and Monaghan
There are a million bland rom-coms that play this kind of dynamic, one that the original
Heartbreak Kid pointedly had no time for. The contrives don't need to be there because the plot forced them to be, it's much more funny if they're only there because of the foolhardy nature of the lead character. So often in the original film, we'll get hilarious scenes where Grodin could potentially get away with a little lie and instead chooses to go for the most elaborate lie possible, with the logic that no matter how crazy it gets, if he just keeps doubling down people will believe him. The remake tries to play that game too, with Stiller coming up with various stories to Akerman about where he's been every time he goes off on some outing with Monaghan. Stiller brings a certain manic energy to these scenes that show he really could take on a role like the original Grodin one, but the writing never seems as interested in these moments as getting to the next gross out or gay panic gag. Stiller gets caught up in an even bigger lie with Monaghan, when she and her family (who she's on vacation with instead of her boyfriend, for some reason) believe Stiller is at the hotel alone and is a widower. This is nastier in a much more interesting way than the rest of the movie, so of course
that lie isn't an active decision Stiller makes. No, instead a series of dumb contrivances lead to the family believing this, because this movie is so often stuck in dumb sitcom land. It feels like the movie having its cake and eating it too, letting Stiller's character off the hook because he didn't
really come up with this awful lie, he just kinda rolled into it and didn't do anything to stop it.
The scenes with Grodin and Eddie Albert in the original are truly wonderful cringe comedy
So, is anyone else besides Akerman even attempting to have fun? Well, Danny McBride & Rob Corrdry are here, and they're both certainly doing their whole "thing"s. Unfortunately, as I've already alluded to, so is Carlos Mencia. Mencia plays the hotel manager, who's a real lovable rascal, if you replace "lovable" with "repugnant". When we first meet him he's lusting over a big box of porn he's just received, and later in the film he tries to trick Akerman's character into giving him a handjob by making her think he's Stiller. He even comes with his own catchphrase: "Screw off! I'm joking, man!" Shockingly, that didn't catch on. That kind of sensitivity extends to the film's general treatment of Mexico as well, which, I don't have time to get into everything wrong with this film, but you can trust me that the representation here is no bueno.
Carlos Mencia trying to remember why we briefly let him be successful
In the end, as often happens in these kind of "big lie" based romcoms, everything blows up in Stiller's face. He gets exposed, both girls leave him, and he gets stung by a jellyfish and has to get peed on by Akerman to soothe the pain (And don't worry, of course we get a close up shot of her
hilariously huge bush!) Stiller (I just realized, is it weird I've exclusively been referring to these characters by their actors' name? If you'd seen the film, I feel like it might feel less odd that I've made that choice..) decides to stay behind in Mexico and drink away his troubles. That is, until his mind is changed by the wise words of sage guru Carlos Mencia, who convinces him he needs to bother this poor girl some more. The only problem is Akerman's character destroyed Stiller's passport in a rage when leaving the hotel. As the late great Jerry Stiller would say: bitches be crazy! What follows is a truly baffling tonal scene in which Stiller escapes across the border with a bunch of illegal immigrants. It's truly hard to tell if the Farrellys want you laughing or feeling sympathetic as Stiller and co repeatedly run into hostile border patrol agents. Finally, the montage of Stiller escaping ends with him on a freight train, only for the passengers inside of it to beat the shit out of him. We don't comment on this, and them throwing him out of the train is the end of the montage; he's back in America in the next shot. It's an incredibly odd moment that barely plays as a joke. It feels like originally it was a longer scene, with the group bonding, only for Stiller to reveal the details of his honeymoon affair, and the guys on the train give him some proper justice in return. But just tossed off casually in a montage it adds to the mean spirited feeling the whole movie has. And the end of the day this movie doesn't off any more interesting thoughts than "isn't it funny when bad things happen?"
We then get a set up for a proper climax to the craziness that's been built here. Stiller knocks on Monaghan's door, only for her family to answer and say she doesn't want to see him. Not content with this answer, Stiller sneaks in Monaghan's bedroom and tries to win her over with a speech he's whispering to her right next to her sleeping husband. If the movie understood how inherently fucked that was, it could manage a solid scene out of that idea. Instead, Stiller actually starts to win Monaghan over, because of fucking course he does. He's only stopped by a surprise attack from McBride, and the commotion of the scene causes Monaghan to come to her senses, and she suddenly remembers Stiller looks like a crazy person and asks him to leave.
So you're saying there's a chance?
Now, logically the story should end there. But instead, we get one last check in, eighteen months later. Stiller's gone and moved to Mexico and gotten in touch with his roots as a perma-vacationer or whatever. He's opened up a shack selling snorkel equipment to tourists, though his business partner Mencia is always trying to rip them off, because 'oh those pesky Mexicans!' That's when he's approached by -- guess who? -- Monaghan. She's down there with the family once again (weird they wouldn't pick a hotel further away from where that crazy guy who stalked one of them works, but hey) and lets Stiller know that it didn't work out with her boyfriend, and that she wants to go on a date that night. A fresh start. Only problem? As soon as she walks away, Stiller's new wife, played by Eva Longoria, shows up to ask who he was just talking to. In theory, I actually quite like this ending. This is the one time where Eddie (have I actually mentioned Stiller's character's name once yet? Well, you can see why I don't want the association) feels like Lenny in the original; constantly in a hell of his own making. But the movie pitches it more as something we're just supposed to go "oh, classic Eddie!" at.
Maxim's Top Hottie of 2005 AND 2006, the industry's greatest honor
So there you have it. The wrong remake made by the wrong people at the wrong time. In addition to being a poor version of the original, it also doesn't succeed at either continuing the Farrelly's only brand of humor that dominated the early 00's, or at adapting to the new Apatow style. Stiller would swiftly recover the following year with Tropic Thunder, only to then fall right back into a series of undercooked leading man vehicles and disappointing sequels, with the likes of Little Fockers, Tower Heist, The Watch and Zoolander 2 all on deck for him. All of which is what eventually moved him to taking a more permanent behind the scenes rol-- wait, what? He starred in a comedy last year? Directed by David Gordon Green? Goddamn, these streaming movies don't exist... Okay well, good for Ben for still being in stuff!
A shot from Nutcrackers. Did ANY of you know this existed?
Speaking of streaming movies that don't exist, that's exactly where the Farrellys ended up post Oscar win. (Apologies to any Ricky Stanicky stans in the house). I really do get depressed by the treatment comedy films get in the streaming world, being dumped and instantly forgotten even more than other non-existent star flicks that end up on those services. Yet it's films like this one that led to that reality. I watched this for free and even I felt a tinge of rage go down my spine at the mere idea I could have gone out and paid $15 to see this (or whatever the absurdly lower price was in 2007). This is a movie where neither the star nor the creative team seem particularly into it, and instead are seemingly holding the audience in contempt for even potentially enjoying it. It's not only a version of the Heartbreak Kid that completely misses what works about the original; it's also the Farrellys retreating to There's Something About Mary mode and fully missing what makes that movie as well. To quote an actually funny movie: what a pisser.
Anyway, please visit my GoFundMe page to support my Mikey and Nicky remake starring Jake & Logan Paul about two chill bros who take on the mob -- with their fists!
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