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The Anguish of the “Old Millennial”

“The Other Two” portrays a micro-generation that’s too young for Gen X complacency and too old for YouTube fame.

Jon Pack / Comedy Central

In the never-ending semantic struggle that is generational terminology (if one thing remains consistent from generation to generation, it is that a giant block of people never know what to call themselves), a new trend has started to emerge. Millennials, which according to pop historians William Strauss and Neil Howe denotes the huge swath of people born between 1982 and 2004, have begun to split into factions. “Older millennials,” those born in the early to mid 1980s, are an unusually lost and precarious group: not quite Gen X, but certainly aware of a world before the Internet controlled our lives. There is a wandering feeling among these thirtysomethings, who, according to a recent financial report, are the most stressed out age group. 

As a member of this floating cohort, I get it; we were adolescents during Clintonian optimism, logging onto the web via our dial-up modems to gleefully surf GeoCities sites before the Internet became a deeply contested, and often treacherous and invasive, space. We weren’t born Very Online, we had to teach ourselves to become that way in order to remain relevant or at least informed. The careers some of us grew up wanting, at least those we saw in romantic comedies—magazine editor, bookseller, owner of a quirky video store—are going extinct. We aren’t as established as our parents, or as tech savvy as the generation zooming up behind us. We can’t afford houses and we don’t really “get” Tik Tok. So where does that leave us? 

This murky, purgatorial zone is challenging for those who live in it, but it also makes ideal fodder for comedy. Comedy often thrives on uncertainty, in the in-between spaces where misunderstandings and confusion sprout like mold. While several shows have deftly portrayed millennial misadventures—Girls, Broad City, Insecure, Schitt’s Creek, You’re The Worst, Silicon Valley, Dear White People, Crazy Ex-Girlfriend, just to name a few—many of them focus on the meanderings and hustles of the ambitious, younger end of the demographic, go-getters with lofty ambitions who can’t quite seem to bend the world to their hunger. But what about the exhausted, run-down older millennials, those who inherited Gen X’s weary Clerks-esque attitude but couldn’t settle into solid career paths like their elders? The Other Two, which is currently airing its first season on Comedy Central, may be the first great comedy to focus on the thirtysomethings who feel sandwiched between existential ennui and otter memes.

The Other Two comes from Chris Kelly and Sarah Schneider, who spent years writing for Saturday Night Live, working their way up to co-head writers before departing in 2016. As a duo, Kelly and Schneider wrote several of the show’s best musical numbers in recent years, many of which (“(Do It On My) Twin Bed” and “Back Home Ballers”) focused on the strangeness of being an adult, particularly one who still relies on their parents for financial or emotional comforts. 

The Other Two extends this joke format into an entire universe. It follows three siblings, two of whom are much older than the third (they are, as it turns out, “old millennials,” a distinction they clarify in the pilot episode). Brooke Dubek (the very funny Heléne Yorke, previously of High Maintenance) is a former aspiring ballerina in her thirties who aged out of a professional dance career into a permanent malaise; when we meet her, she is squatting in an empty model apartment in Manhattan inside a building where she works as a low-level real estate broker. She oversleeps, wakes up with her face in a slice of cold pizza, and tries to hide the evidence of her presence when another broker walks in and finds her trying to stuff the pizza box into a dryer. She is summarily fired, back on the hunt for work again. Her slightly younger brother, Cary (Drew Tarver), is an actor in New York who cannot seem to book a role. He keeps auditioning for lackluster parts like “man who smells fart” in commercials, and even then, he falls short and falls back into his restaurant job until the next opportunity comes along. 

Both Cary and Brooke know they are running out of time to “make it”—even though motivational posters claim that success has no hard deadline, these characters are grounded enough to know that stardom does, and they are rapidly approaching it. They both pursued more traditional (and very “older millennial”) paths, while trying to break through: Brooke attended a competitive dance academy as a teen, while Cary moved from Ohio to the big city and started hoofing it to castings. They were both born just a little too late to become YouTube famous, or to pull the lucrative scam that is becoming a full-time Instagram influencer.  

Their tween brother, Chase, on the other hand, rides these new modes of exposure to global fame without even trying. When the show begins, Brooke and Cary learn from their mother Pat (Molly Shannon, who, with her Kate Gosselin hairstyle, bedazzled tunics, and manic energy, fully looks the part of the upstart momager) that Chase (Case Walker) has gone viral. His saccharine, homespun video for a squeaky pop song called “Marry U At Recess,” is an Internet sensation, earning him an appearance on the Today Show and an immediate record deal. Chase, who with his Mouseketeer dimples and flat-brimmed caps is clearly a nod to a young Justin Bieber, is happy with the attention but more or less indifferent to fame. It is Pat who pushes him to professionalize, moving her 13-year-old son to Manhattan so that he will be closer to industry types. She hires a schmoozy manager named Streeter (Ken Marino) and a no-nonsense publicist (Wanda Sykes, who repeatedly steals scenes). With “Team Chase” in place—including a group of nameless pop hook writers who provide the singer with his next hit, “Stink” about, well, dancing so hard you smell bad—all the adults present strap in for the rocket ride that comes with latching oneself to a promising teenage talent.

And then, there’s the other two. What makes this show about a lonesome, lost generation is that Brooke and Cary don’t immediately resent Chase’s opportunities, even though their trajectories have been so rocky and uninspired. They are far too burnt out to feel ire, or even the desire to exploit their brother for their own gain. That kind of opportunistic leeching is reserved for the older characters, like Streeter and Pat, who see Chase as a kind of cash cow and golden ticket to their second act. Instead, Cary and Brooke seem mildly amused by the shift in their family dynamic, and see that in assisting Chase with his career, they might be able to regain some of the purpose that the world beat out of them. Brooke swallows her pride to become Chase’s assistant, which at first feels menial to her but increasingly becomes a point of pride. She finds she is far more capable than she ever gave herself credit for: hauling a woozy, drunk Chase out of his nightclub birthday party (sponsored by Voss water) to safety; calming down a throng of screaming fangirls on the chartered flight where Chase launches his new album, making tough calls about Chase’s costuming and set design. 

Cary has a different journey, but it too is one of self-discovery. For most of his career, Cary has been denying who he really is, often denying or downplaying his identity as a gay man. He is in a confusing make-out relationship with his frat boy roommate (who insists that he is absolutely heterosexual), and he seems uncomfortable with being openly gay in auditions or on social media. When Chase publicly outs his brother with a single called “My Brother’s Gay (And That’s Ok),” Cary starts to flail. In a fast-paced farcical sequence that would delight Noel Coward, Cary first demands that Chase’s publicist remove the video, until he learns it is trending. Then there is backlash, and then backlash to the backlash. The Other Two is an extremely studied parody—the years at SNL have honed Kelly and Schneider’s scalpels—and Cary’s frenzied, flip-flopping reaction to his 15 minutes of Twitter fame is as accurate as it is outrageous. As a millennial just a bit too old to know how to react to online fame with any modicum of chill, he proceeds to lean too far into his notoriety, getting a Cheeto-orange spray tan and bleaching the tips of his hair.

What The Other Two is really about is rapid adaptation. The world is changing, and so is fame, and it takes Cary and Brooke several episodes to get with the program. When Brooke boasts to Chase’s publicist that the Internet is calling her a “white feminist,” she has to be told that this isn’t a good thing. When Cary leaps on stage at Chase’s packed birthday party to sing his brother an ode, he quickly learns the dangers of performing without autotune. But the siblings adapt to Chase’s celebrity with far more grace than their mother, who, living her “Year of Yes,” starts to act out in wild ways, like taking so much ecstasy at a club that she proceeds to sit on the dance-floor to count out a pile of mixed nuts. Brooke and Cary band together to create a new parental unit, both for their younger brother and their newly liberated mother. They find meaning in the in-between, in being the relatively stable filling in their family sandwich. 

If The Other Two has a message, it is that being in the middle, as a generation and as an individual, is hard. You feel lost, overshadowed, unheard. There is a reason old millennials are so stressed out all the time. But there can also be pleasure in defining for yourself what it means to grow up, and what it means to fall through the cracks. Sometimes, down there in the crevasse, you learn how to climb out.

*An earlier version of this article revealed details of an episode that has not yet aired.