When cinema history is written, what gets highlighted most often are the films that made an indelible mark: films that were beloved by critics, represented a particular cultural moment, or become a popular phenomenon. The films that aren’t often written about are the outliers: films that don’t make much sense in their context, didn’t function as an index of a larger cultural moment or trend, or didn’t make for significant hits or misses. However, with hindsight, those strange films that don’t belong, films orphaned without a definite place in history that can be made sense of, can eventually reveal themselves to be the most interesting, be they good or bad.
2001 was a strange year for comedy. In the latter part of that year, it seemed we needed a laugh more than ever, but no single film really filled that void. Unlike Meet the Parents in 2000 or My Big Fat Greek Wedding in 2002, 2001 was without a mammoth comedic hit. The once-crowned Farrelly brothers released the first of a string of underwhelming, forced films, and a gap in popular comedy cinema persisted until Judd Apatow turned a litany of non-photogenic sitcom stars into bona fide movie stars in 2005. Sure, 2001 had the expected combination of the hit sequel (American Pie 2), the romantic comedy (Bridget Jones’s Diary) and one genuinely inspired star-maker (Legally Blonde), but the comedy movies that existed just on the margins of the radar, if not off it entirely, reveal a crop of strange, ballsy, even subversive films that both reflect the unique identity crisis mainstream cinematic comedy was undergoing at this point as well as a glimpse of what popular movie comedies might have been had history turned out differently.
They aren’t all masterpieces, but they are all worth watching if only for the audacity of their very existence.
Company Man (dir. Douglas McGrath)
Released: March 9
Emma director, Bullets Over Broadway co-writer, and virtually unknown actor Douglas McGrath cast himself as the lead in this ensemble about a mild-mannered high school grammar teacher who fibs to his father-in-law that he’s a member of the CIA in order to gain respect and, naturally, finds himself at the center of the Bay of Pigs invasion. Company Man has an attractive cast including Sigourney Weaver, John Turturro, Alan Cumming, Ryan Philippe, Denis Leary, and Anthony LaPaglia as none other than Fidel Castro himself, all of whom proceed with absolute confidence in the strength of the source material. Company Man is an incredibly strange brew of early 1960s pop culture references, arguments about correct grammar, and jokes predicated on the audience’s presumed rock-solid memory of the earliest moments of the Kennedy administration. Oh, and there’s a Woody Allen cameo.
It’s difficult to ascertain exactly who Company Man was made for. The film proceeds with a fill-in-the gaps élan a la Dick two years earlier, but relies on concrete recollection of a significantly older even and replaces two teenyboppers with, again, a high school grammar teacher. While the “gags” are obscure, one can’t help but admire the dedication, sincerity, and palpable charm of McGrath’s effort (with co-writer Peter Askin) to make the all-star grammar-teacher-lost-in-Cuba-during-a-foreign-policy-disaster film that none of us knew we’d always been waiting for. If only Company Man were released in the age of Mad Men…
Josie and the Pussycats (dir. Deborah Kaplan & Harry Elfont)
Released: April 11
Josie and the Pussycats was supposed to be yet another Hannah-Barbera live-action adaptation. But instead of another The Flinstones (directors Kaplan and Elfont helmed Viva Rock Vegas one year earlier), Josie and the Pussycats instead turned out to be a scathing satire of the music industry’s shameless manipulation of young people into consumer slavery. That Josie and the Pussycats was released while the 90s boy band craze was till in full swing (and during one of the most vacuous and uninspired moments in popular music across all genres, if you ask me) only gives weight to the film’s timely and scathing critique of an industry that studio filmmaking is highly invested in.
Incorporating early-00s markers of pop-cult synergy like Total Request Live, subliminal advertising, and Seth Green, Josie and the Pussycats banks off the accelerated consumer culture of the initial years after the dot-com bust just as it lays waste to the same culture with a narrative about government corruption and covert assassination. This is not a subtle satire, and that’s exactly what makes it stand out, as Cole Abaius argued in an impassioned defense of the film a few years back: “Which is precisely why [Josie and the Pussycats] is such a digestible movie on the surface – because the satirical message it carries has to be delivered in such a cartoonish fashion.”
Freddy Got Fingered (dir. Tom Green)
Released: April 20
Remember Tom Green? He was that former cable access TV host who put cow udders in his mouth, woke his father at all times of the night, and became incredibly famous during what was perhaps the very last moment that MTV attempted to evoke anything resembling “edge.” At the height of his power, Green wrote, directed, and starred in a studio-funded feature film in which he was given near-total creative control that opened in theaters all across the nation. Oh, and he titled the movie Freddy Got Fingered, a reference to a false claim that Green’s character makes to his father (played by Academy Award nominee Rip Torn, here reduced only to curse words and hand gestures) accusing him of childhood molestation.
I was fan of Green in my early teen years, but his appeal as a comedian is completely lost on me now. There’s nothing intelligent, insightful, or truly subversive about his comedy. However, at the same time, I can’t help but admire the audacity of Green using his capital (which he probably realized might not last) to make something so perverse and utterly devoid of meaning. Freddy Got Fingered eschews any conventional film function, including narrative logic and empathetic characterization, replacing them with a sausage keyboard and prolonged portrayals of a man’s attempts to impress his father that are pained to the degree that they make you wonder if this film was Green’s $14 million therapy project. On the surface, however, it’s Salo meets early Internet humor, and that’s something.
Pootie Tang (dir. Louis C.K.)
Released: June 29
If Louis C.K. were to direct a feature film today, its release would be attended by mounting anticipation from nearly anyone who enjoys laughter. In 2001, however, C.K. was a successful comedian but not one whose popularity and persona extended beyond the Comedy Central rotation. How he and co-writer Chris Rock were able to convince Paramount Pictures to finance a feature film about a character who was probably featured for no more than fifteen minutes total on The Chris Rock Show, speaks a language that is decipherable only to the other characters in the film, and is embodied by a writer, not a known actor, is beyond me.
Pootie Tang is an evident mess to anyone with eyes, was edited heavily by the studio, and flopped at the box office. But, looking at the film over ten years later, it’s clear that these behemoths in the comedy world were attempting something compelling in their dogged pursuit of the anti-movie. Scott Tobias explained Pootie Tang thusly when he entered it into the AV Club’s “new cult canon”: “The flashes of genius in Pootie Tang are chased by stretches of hyperactive inanity, but it’s one heck of a wild ride—jagged, episodic, at times nonsensical, and funny in ways that are completely unexpected and wholly original.” With Undercover Brother and Goldmember, the early-00s was never short on ‘70s pastiche, but Pootie Tang mixes an oft-forgotten blaxsploitation trope, guerilla filmmaking, and an overabundance of irreverence that is sometimes frustrating but sometimes hilarious.
Wet Hot American Summer (dir. David Wain)
Released: July 27
Now a solidified cult hit that caotured early-ish work by some of the most popular comic figures in movies and on TV (the film’s impressive roster sports Elizabeth Banks, Paul Rudd, Amy Poehler, and Bradley Cooper amongst others), Wet Hot American Summer hardly raised an eyebrow on initial release. There are a few films I’ve seen in my life that truly expand the notion of what a film comedy can be, finding humor in things I could never imagine or envision as funny, much less hilarious. A can talking to a Vietnam veteran is one of them, which is why Wet Hot American Summer stands alongside Monty Python and the Holy Grail and Young Frankenstein in my personal comedy pantheon (it’s on my desk).
But what’s really interesting about Wet Hot is, like Pootie Tang and (arguably) Company Man, it finds inspiration through rendering parodic something that seemingly never asked for parody: in this case, sex-starved youth camp comedies of the ‘80s like Meatballs, Porky’s, and literally nothing else I can think of. Wet Hot American Summer makes fun of a comedy and still comes out transcendently funnier than the source of its inspiration. Today, Web 2.0 is overloaded with the type of goofy, unmotivated humor that Wet Hot revels in with perfect comic timing. It’s a film far ahead of its time, and it’s also the reason why I still see the unfunny films Wain and co. have made since.
Zoolander (dir. Ben Stiller)
Released: September 28
Zoolander is the only film on this list that can be deemed a mainstream success of sorts, but that doesn’t make Stiller’s “satire” of the modeling industry and third outing as director any less bizarre. If anything, it’s the mainstream coda for the strange, subversive, marginalized comedy of 2001 that came before. Like Pootie Tang, Zoolander is a character based on a comedian’s TV show that nobody was asking for a feature film adaptation of, but unlike Pootie Tang, Zoolander attempts to connect its silly vignettes with a thin-yet-present semblance of a plot, in this case the attempted assassination of the Prime Minister of Malaysia that Zoolander must attempt to thwart.
Zoolander is excessive, finding its laughs through giant sets, elaborate costumes, celebrity cameos, and a David Fincher-like approach to sleek visuals. Strangely enough, it works. As a satire it hardly runs deep, but as a farce heavily invested in its own self-aware stupidity, moments of Zoolander represent the best dumb comedy mainstream cinema can come by. Zoolander casts a who’s who of early-oos comedians, and lets them take their performances to 11. While the charms of Stiller’s Zoolander stall before the film’s end, a pre-superstardom Will Ferrell’s sexually repressed, corset-wearing, snow-haired Mugatu finds him at the height of his comic inventiveness. And the baton of idiosyncratic humor was passed.