Jonah Hill was everywhere in the 2010s. After breaking through with his hilarious performance in the now-seminal, near-perfect 2007 teen comedy Superbad, Hill booked a bunch of lead and/or prestige roles, and for most of the 2010s he was a fixture in his own comedies (Get Him to the Greek; the 21 Jump Street movies), ensemble comedies (The Watch; This Is the End); animated voiceover gigs (the How to Train Your Dragon movies; The Lego Batman Movie; less for kids, Sausage Party); and, perhaps most impressively, movies for distinctive auteurs including Martin Scorsese (The Wolf of Wall Street), Bennett Miller (Moneyball), and brothers Coen (Hail, Caesar!) and Duplass (Cyrus). But only one movie combines all three dimensions of Hill’s career, and that must be why it’s been trending on the HBO Max charts: Yes, America has finally embraced The Sitter – as well as the unrated cut of The Sitter, which joined the original version of the film on the HBO top ten this week.
Hear me out. The Sitter might seem like Hill’s nadir, a 2011 bomb that earned some career-worst reviews for its director. But because that director is David Gordon Green, it checks all of the major Hill boxes. It’s a broad comedy where Hill talks fast and foulmouthed in situations where he’s well over his head; it has a kind of kid-comedy component, even though it’s rated R (or has no rating at all), because it’s a riff on Adventures in Babysitting; and it’s directed by a distinctive auteur.
Green may not have quite the prestige of a Scorsese or the Coens, but that seems to be by design. His eclectic career includes Malick-inspired indies like All the Real Girls and George Washington; the Halloween sequel trilogy; and some broad comedies like Pineapple Express and Your Highness, the latter of which came out the same year as The Sitter, a potent double feature for the “what the hell is this guy doing?” crowd.
As with a lot of strange career moves, this one makes more sense in retrospect than it did in the moment. Knowing that Green followed a trilogy of stoner-ish comedies with another trio of indies featuring back-to-basics performances from the likes of Nicolas Cage, Al Pacino, and Paul Rudd makes a movie like The Sitter seem less like a dead end. But you know what? This movie was always pretty good, which makes sense. Green has directed movies with almost everyone in Hill’s Apatow Boys peer group: Seth Rogen, James Franco, Paul Rudd, Danny McBride (he was Green’s first!).
Admittedly, Green’s eye for post-industrial decay is better-used in Pineapple Express – though his frequent cinematographer Tim Orr is present here, too. But for a crude comedy where an unfit babysitter takes his trio of young charges on a nighttime adventure through New York City featuring drugs, violence, and sex (or at least, the promise of sex for Noah, Hill’s hapless character), Green maintains the affection for his characters that runs through all of his work. The man simply regards people in general with affection, which means a subplot about oldest sibling Slater (Max Records) struggling with his sexuality (and Noah being the one to pick up on this) is handled with unusual sensitivity. Rather than a cheap save-the-cat moment, we realize Noah is a worthwhile guy because, despite his immaturity and vulgarity, he’s able to observe a way that Slater could use his otherwise-unqualified help. Like Superbad (and like too few of his comedies since), the movie channels Hill’s frantic energy into a stealth monologue of his secret insecurities.
Even the villain of the piece, drug dealer Karl (Sam Rockwell), is too endearingly funny truly dislike. Rockwell, reuniting with Green after the much more serious Snow Angels, gets license to go Full Weirdo, giving an appropriately hammy and freewheeling performance. If you’re going to use the creaky one-crazy-night structure, it helps to have a guy who seems genuinely unhinged as your antagonist. Rockwell obliges. Honestly, he’s better than at least a couple of that year’s nominees for Best Supporting Actor. I’ll leave for you to decide whether that includes Hill. Just kidding; it doesn’t! He’s quite good in Moneyball. But I would definitely rather rewatch The Sitter. The longer, unrated cut runs still only runs 88 minutes! The regular cut throws to the end credits around the 76-minute mark. You can watch both versions of The Sitter in less time than certain Transformers movies.
Still, some of The Sitter’s value in Hill’s career does relate to the benefits of hindsight. At the time, The Sitter was less successful with critics or audiences than Get Him to the Greek, a Forgetting Sarah Marshall spinoff that became Hill’s first big starring vehicle. Now, a movie co-starring Russell Brand and P. Diddy about music-industry debauchery seems downright cursed. The Sitter, on the other hand, features the final film appearance of beloved character actor Nicky Katt, as well as Ari Graynor, Jessica Hecht, JB Smoove, and Method Man. A cast you can set your watch to! By which I mean were not ever in court for sex crimes!
Despite bouncing back from The Sitter with his Jump Street movies, Hill hasn’t been especially visible in the last few years. He did the obligatory Netflix comedy in the sometimes funny but overinflated You People, opposite Eddie Murphy, and is making his second film as a director for Apple. You People is a great example of a comedy that seems smarter and more self-aware than The Sitter, and yields far fewer actual laughs. Maybe Hill should check out his supposed nadir on HBO sometime, too.
Jesse Hassenger (@rockmarooned) is a writer living in Brooklyn. He’s a regular contributor to The A.V. Club, Polygon, and The Week, among others. He podcasts at www.sportsalcohol.com, too.