For much of the 2000s, Ben Stiller was one of the biggest movie stars in America. In 2004, for example, the same year that Jude Law notoriously appeared in half a dozen movies, mostly flops, Stiller casually appeared in six movies, too – and astonishingly, five of them were hits, including one (Meet the Fockers) that remains the biggest of his career. But though he had begun a high-profile directing career in the ’90s, Tropic Thunder was the only one of his big hits of his 2000s peak that Stiller directed himself. So far in the 2020s, he’s pulled off a surprising reversal: While he’s only starred in one movie in the past seven years, he’s gotten plenty of attention as the producer and series-establishing director of Severance, the hit sci-fi drama on Apple TV+.

At first glance, Stiller’s work on Severance seems more connected to his gig directing the miniseries Escape at Dannemora than any of his feature films. The most famously enduring of those, Zoolander and Tropic Thunder, are both silly-smart goofs on the entertainment industry, with Stiller playing a clueless male model and arrogant Hollywood action star, respectively. The Cable Guy, too, is a media satire, albeit a darker and less cuddly one. Stiller’s most recent film as a director is still Zoolander 2, but his most filmmaker big swing was a long-gestating remake of The Secret Life of Walter Mitty, and an in-depth 2012 New Yorker profile gave ample behind-the-scenes detail of Stiller struggling with his image as a comedian and his hopes that Walter Mitty, a life-affirming story of a daydreamer who works to live out his fantasies, would chart a new path in his directorial career. When the film finally emerged in 2013, it was received, correctly, as saccharine and middling, the kind of overblown life lesson that other Stiller movies might kid relentlessly.

Yet there is some kind of connective tissue between Walter Mitty and the darker, weirder Severance, and not just because Adam Scott has a supporting role in the former. (Or the menacing Ólafur Darri Ólafsson, for that matter.) In Mitty, the titular character (played by Stiller) works at the LIFE magazine archives, set in an alternate present where the magazine still exists, but is about to shut down; Severance also focuses on an office drone and a sort of retro-contemporary office life, with the added nightmare that “severed” workers allow a different consciousness to emerge and perform their daily tasks. Essentially, a separate personality is siphoned off and imprisoned to perform drudgery. Rather than spending days at the office fantasizing about a more glamorous life, severed workers can detach from their jobs entirely.

It’s an irresistible and also vividly claustrophobic concept from show creator Dan Erickson – not directly from Stiller himself. But Stiller has directed 11 of the show’s 19 episodes, far more than the first-three-and-split strategy often employed by big-name filmmakers moving over to TV. He’s received particularly strong notices for the distinctly wintry color scheme and visual texture of the series, which ended its second season with a Logan’s Run-ish shot that, as Stiller helpfully informed a fan who had tweeted about the show, was shot digitally, then transferred to celluloid to achieve that particularly grainy look.

Stiller has always been a more technically precise director than many of its comedy peers; Tropic Thunder takes great care to replicate the big-budget look of various Hollywood productions, including the war epic that goes awry as the film’s main story. Walter Mitty is a very polished film – overly so, with a slick digital clarity that Severance musses up even as it’s composed with similar exactitude. Severance also has some of the satirical edge of Stiller’s spoofier movies, mixed in with the more grounded social satire of his first film, Reality Bites.

At the same time, there’s something unconstrained, even a little sweaty, about the second season of Severance that’s reminiscent of Stiller’s weaker movies, too. The much-discussed finale has some dynamite best-of-show scenes, like the sequence where Adam Scott’s “innie” and “outie” versions converse and argue with each other via video messages, and memorable images, like that red-siren hallway at the end. It also rambles on for nearly a feature-length runtime, throwing back to the least disciplined shows of the Peak TV era. Stiller also directed “Sweet Vitriol,” the eighth episode of the season – the one focusing entirely on Cobel, Patricia Arquette’s character. It’s a great idea for an episode, weighed down by the show’s season-long habit of drawing out its story while leading the audience into cryptic cul-de-sacs. What actually happens with Scott’s Mark in the back half of the season? He attempts to “re-integrate” his two personalities in the sixth episode (“Attila”), spends some time having unconscious flashbacks, calls in sick to work, and then the events of the finale unfold. The show isn’t exactly withholding, like the most frustrating long-form mysteries; the finale offered some key pieces of information. But it also doesn’t seem to feel that, say, eight 44-minute episodes could regularly do it justice.  

This prestige-TV lollygagging can’t be blamed on Stiller, of course, who isn’t a writer on Severance. But the second season does have some of the strenuousness that characterizes Stiller’s last few movies: the “heartfelt” machinations of Walter Mitty, plus the straining to sequelize of Zoolander 2. He wouldn’t be the first director to venture into try-hard territory; that’s practically the job description. But it does feel like some of the insecurities that he mines so precisely for comic tension have a more serious flipside behind the camera. Severance pulses with anxiety even when its characters insist that they’re happy; it’s what makes the show such a memorable evocation of office life. But that’s ultimately not necessarily a world Stiller, born into an acting family, has much experience with. That’s presumably what, in part, has made him such a savvy pop-culture mimic and satirist, and his willingness to puncture those cheery mediated images is what makes a movie like The Cable Guy or Tropic Thunder so effective — and what makes Walter Mitty feel so phony. Some of Severance‘s second-season indulgences make more sense when you notice, beneath its grief-stricken buzz of labor dissatisfaction, the satirist and comedian who still yearns to be taken more seriously.

Jesse Hassenger (@rockmarooned) is a writer living in Brooklyn podcasting at www.sportsalcohol.com. He’s a regular contributor to The A.V. Club, Polygon, and The Week, among others.