April’s​ Movie of the Month, the Mark Waters comedy Head Over Heels, is many disparate films tied up in a single package. At times a formulaic romcom, a Farrelly brothers-style gross-out comedy, a diamond heist action thriller, and a winking Hitchcock homage, this Freddie Prinze Jr./Monica Potter madcap romance is largely a fun watch due to its violent, unexpected shifts in genre & tone. At its core, however, Head Over Heels can be readily understood as a light-headed satire of the fashion industry. Constantly poking fun at Monica Potter’s befuddled lead’s supermodel roomates, borrowing some of their second-hand glamor for its central romance fantasy, and staging its climactic showdown on a Fashion Week runway, Head Over Heels is a silly, parodic stab at couture culture. It was not alone in its year of release, either. The similarly silly, but much more popular Ben Stiller comedy Zoolander also arrived in 2001, with its own jokes about fashion models’ supposed stupidity and its own climactic runway-set showdown. Head Over Heels & Zoolander share more than just their deliriously silly fashion world parody too. They also undercut the frivolity that drives their central fashion world gags with some truly depressive, cruel lines of pitch black humor, diving much deeper into the darkness of the human soul than you might expect from a Freddie Prinze Jr. romcom and a ZAZ-style comedy that proudly features a Fabio cameo.

Fashion models seem to lead surreal, absurd, almost inhuman lives. Zoolander & Head Over Heels build their humor around that perception. They introduce a “normal” person (movie-normal anyway; one’s an art-restorer and one’s a photo-journalist for TIME Magazine) into the otherworldly realm of superhuman fashion models, or in Zoolander‘s parlance “people who are really, really, ridiculously good-looking,” to play off that eccentricity. Part of the humor they find there is in jealousy: lavish parties, beautiful clothes, a total lack of sexual inhibition, etc. are overwhelming to the two films’ non-model normies and both movies have a lot of fun indoctrinating them into this culture, which appears to be a live action cartoon from the outside looking in. To take the models down a peg, then, they also poke fun at the two things typically associated with people who are really, really, ridiculously good-looking: low intelligence & eating disorders. Zoolander is a lot harsher on both of those topics than Head Over Heels. The Mark Waters film is a lot more humanizing in its portrayal of its star’s supermodel roomates, who are eventually proven to be a lot more cunning & self-aware than any of their foils give them credit for. I don’t really see the point in diving into the particulars of either films’ jabs at bulimia or stupidity, though, since it’s the easiest, most common sources of humor you’d expect from any fashion world comedy. What interests me, and I think what makes these films memorable, are the more unconventional places they find their dark humor, the real weirdo shit.

At its core, Head Over Heels is a much sweeter movie than Zoolander, with more of a sincere focus on its milquetoast woman/fashion world weirdo romance. That doesn’t mean it doesn’t indulge in its own forms of pitch black humor. The reason our generic romcom lead puts herself on the market for a new man at the beginning of the film is that her old biddy coworkers keep announcing, plainly, “You are going to die alone.” She then has her “meet cute” moment with Freddie Prinze Jr.’s hotshot fashion exec when the dog he’s walking tackles & mounts her in the lobby of their apartment building, which is a special kind of brutally embarrassing public humiliation for a cutesy romcom. The movie later indulges in other similar raunchy comedy moments, like a stray cunnilingus gag or an epic scene where the leads’ fashion model roomates are covered head to toe in human feces. What’s even darker is that the movie’s entire romcom plot is built on a Rear Window moment where the lead witnesses the fashion exec hunk “murder” someone through his apartment window, but romantically pursues him anyway, because of their overwhelming sexual chemistry. This includes a scene where she bangs the possible murderer before he’s convincingly absolved of the crime, an act her roommates gleefully watch through the window as if it were a plot point on a daytime soap. Sometimes these models’ lack of sexual inhibition is played for light laughs, like in an early scene when they aggressively catwalk nude through their apartment’s shared living space. Sometimes it gets much darker, though, like when the Russian-born model casually accuses a Girl Scouts troupe of being a childhood prostitution ring or when the Australian-born model (who has a crippling addiction to plastic surgery) constantly makes casual references to being molested by her uncle as a child, which is played for laughs. For all of its indulgences in cutesy romcom tropes, Head Over Heels can be a deeply strange, deeply fucked up comedy.

Much like how Head Over Heels builds its madcap romantic mixup around a possible cold-blooded murder, Zoolander finds its humorous A-plot in a conspiracy to assassinate the prime minister of Malaysia so that child labor laws will relax enough in that country for fashion clothing production to pinch a few pennies. That’s pretty fucked. Its dark soul wasn’t lost on critics at the time of its release either. Ebert famously wrote in his post-9/11 review of the film, “There have been articles lately asking why the United States is so hated in some parts of the world. As this week’s Exhibit A from Hollywood, I offer Zoolander, a comedy about a plot to assassinate the prime minister of Malaysia because of his opposition to child labor.” Besides that boldly crass plot line (which does have a pointedly satirical jab at fashion as an industry built into its DNA) and its much harsher stance on models being oversexed, anorexic idiots than the one taken in Head Over Heels, Zoolander ups the stakes of its dark humor by actually claiming a few human casualties. While the witnessed “murder” of Head Over Heels turns out to have been faked, one of Zoolander‘s first big gags (and easily the one that got the biggest laugh out of me as a teen at the theater) involves four of its idiotic lead’s closest male model friends perishing in a gas station explosion. It’s the kind of gag that you’d expect to see in the icily funny mockumentary Drop Dead Gorgeous, where the punchline is a smash cut to a funeral service. Later in the film, the fashion industry is again skewered when Ben Stiller’s male model lead participates in a runway show that exploits/appropriates the tattered rags of the world’s “crack whores” & homeless for a marketable fashion aesthetic. And the darkest joke of all is that the film’s very first celebrity cameo (one of thousands) is none other than Donald J. Trump. Yikes.

As harsh as the humor can be in both of these movies, they’re still largely absurd, silly, light-hearted films. In both Head Over Heels & Zoolander, initial competitive jealousies in an industry where vanity is everything eventually give way to heartfelt camaraderie. Initial unease with the fashion world’s liberated, uninhibited sexuality eventually leads to sexual & romantic satisfaction. Models considered to be useless idiots at the outset save the day & prove their worth as human beings. Still, there’s a dark soul lurking at the center of both Head Over Heels & Zoolander, a black comedy undercurrent that occasionally cuts through the deliriously silly fashion world parody to laugh in the face of betrayal, death, bulimia, child abuse, etc. 2001 not only saw the release of two energetically silly fashion world comedies; it also brought out a surprisingly corrosive spirit in each of them that can disrupt & subvert the cheeriness of their shared mainstream comedy surface. Both movies were better & more memorable for it.

For more on April’s Movie of the Month, the Mark Waters fashion world romcom Head Over Heels, check out our Swampchat discussion of the film.

-Brandon Ledet