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‘The Last O.G.’ ‘High Maintenance,’ and the Brooklyn Show in 2018

Two recent series set out to capture the latest iteration of the ever-changing borough; that task, like its inspiration, is more complicated than it appears

Cast members from ‘High Maintenance’ and ‘The Last O.G.’ in front of the Brooklyn Bridge HBO/TBS/Getty Images/Ringer illustration

“What happened to Brooklyn?!”

Thus ends the cold open of The Last O.G., in which newly ex-con Tray Barker (Tracy Morgan) discovers that his desire to help his community may no longer apply to a community awash in strollers and non-dairy milks. The TBS half-hour shares a setting, and a satirical subject, with its network sibling Search Party: a borough rendered unrecognizable by real estate developers and their trend-chasing customers. But as the title implies, The Last O.G. takes on the perspective of the gentrified over the gentrifier. Tray has spent the last 15 years in prison on a drug-dealing charge, meaning that he experiences more than a decade’s worth of change in one single, overwhelming rush. In this new Brooklyn, the audience sees what Tray sees—something equal parts unsettling and amusing.

Brooklyn has a storied history as a TV environ, and not just as the untamed borough Miranda bravely ventured into during the later seasons of Sex and the City. Mirroring its real-life counterpart, fictional Brooklyn has long been an enclave where New York City’s marginalized populations could form a community that centered themselves, far away from the white, WASPy, and wealthy Manhattan power structure. On The Honeymooners, Jackie Gleason cast himself as a working-class bus driver. The ensemble cast of Welcome Back, Kotter was specifically intended to reflect the diversity of its Bensonhurst setting. The affluence of The Cosby Show’s Huxtable clan may have been aspirational, but it was deliberately rooted in an actual center of African American life. (Shows like Everybody Hates Chris and Living Single would later tweak the Cosby Show template to depict life in the same community from a less idyllic and more young professional point of view, respectively.)

Lately, the Brooklyn show has evolved to reflect the borough’s changing demographics, which include a disproportionate number of people who get hired to make loosely autobiographical shows about their 20s. Lena Dunham’s Girls caught an unprecedented amount of heat for the overwhelming whiteness of its core cast, though the real outrage might have been how representative it was of a certain New York creative class. Broad City set an entire episode at the Gowanus Whole Foods, while Master of None’s Dev Shah lives in an impeccably curated Williamsburg loft just a stone’s throw away from an artisanal coffee source. Even CBS caught onto the trend: 2 Broke Girls spent six seasons translating hipster stereotypes into jokes broad enough for a studio audience.

The Old Brooklyn Show and the New Brooklyn Show have largely existed as two disparate genres, with the underlying implication that their protagonists’ lives never meaningfully cross streams. Last year, Spike Lee’s reimagination of She’s Gotta Have It for Netflix distinguished itself by acknowledging that these seemingly separate Brooklyns were coexistent and took the uneasy relationship between the two as its central theme, albeit with mixed results. The Last O.G. shares Lee’s ambitions to represent Brooklyn in its totality, not just in segments. So, in its own way, does the anthological HBO series High Maintenance, which strives toward a similar middle ground from a very different starting point. Neither series has perfected the admittedly tricky balance between parody and pathos or old school and new, but in the process, both are working toward a third kind of Brooklyn Show: one that captures, and celebrates, a borough in flux.

Cocreated by Get Out’s Jordan Peele, The Last O.G. zeroes in on this often awkward cultural cross-section. A crucial part of this effort is Tray’s ex-girlfriend Shay, played by Tiffany Haddish in her first major role after her breakout turn in last year’s Girls Trip. In Tray’s absence, Shay put herself through school, had two children, and got married to an inoffensive white guy named—what else?—Josh. She still lives in the neighborhood, just in a renovated brownstone with stainless steel appliances.

Where Tray is stuck in an older version of Brooklyn and can’t fully adjust to the new one, Shay occupies both at once. She seamlessly pivots from charming older white donors for a nonprofit to ripping Tray a new one for showing up unannounced; when someone taps her on the shoulder in front of the housing project she and Tray used to call home, she instantly throws up her fists. “You shouldn’t run up on me like that,” Shay cautions the stranger, while Josh looks on stunned. She’s ideally positioned to dig into the messy dynamics of change: what’s lost when money and transplants flow into a neighborhood, what’s gained, and why gentrification doesn’t necessarily split an area into two distinct eras or populations.

Unfortunately, The Last O.G. seems less interested in Shay as a person in her own right than in a prize for Tray to work toward. I’ve seen more than half of the 10-episode first season, and the show still hasn’t revealed how she and Josh first met, had her explain what she sees in her new husband, or gone in-depth on the how and when of her upward mobility. She’s also saddled with a backstory that puts her dangerously close to a cartoonish traitorous-ex type: Shay didn’t visit or communicate with Tray once during his 15 years behind bars and never told him about the teenage twins who are biologically his. Such borderline cruelty neither squares well with the patient, empathetic Shay we come to know nor helps her connect with the audience. Which is a shame, because The Last O.G. is at its best in a scene set at the repast for Shay’s mother’s funeral, in which Shay reams her family and friends for begrudging her hard-won success.

The Last O.G. consistently uses Tray’s surroundings, Shay included, as a window into his feelings, rather than the reverse. This isn’t inherently an obstacle to The Last O.G. as a television series, but it is to the show as a social satire, and The Last O.G. never offers an alternative vision of what it wants to be. Morgan’s central performance—his first lead one since a near-fatal car accident in 2014—is warm, inviting, and crucial to selling scenes like one where Tray learns he can’t catcall customers at the Blue Bottle–like coffee shop where he lands a barista gig, because that’s sexual harassment. But the character himself isn’t quite rich enough to hang a whole series on, at least stripped of all the larger social forces and hilariously specific manifestations thereof that affect him.

Some of The Last O.G.’s sharpest moments take place in the halfway house Tray calls home, the residents exchanging nihilistic banter about the difficulties of readjusting to life on the outside. (“Go on a date, man. It’s healthy.” “Fuck you know about healthy? You’re a sex offender!”) Yet these interludes are far outnumbered by sincere, even saccharine subplots—a “truth safari” revisiting his past, a father-son bonding episode about changing conceptions of masculinity—or overbroad physical comedy. In the same episode where Shay makes that moving speech at her mother’s memorial, Tray jumps out a window to get away from a prison groupie played by This Is Us’s Chrissy Metz, and the house shakes when they finally have sex.

The Last O.G. may be uneven, but the premise remains solid, and the combination of Morgan, Haddish, and Peele with exceptional ratings should buy it time to iron out the kinks. In the meantime, a show that embraces Brooklyn’s contradictions, merely the most accelerated version of a development boom overtaking many of the nation’s urban centers, is worth waiting for.

Since its Vimeo debut, High Maintenance has been a portrait of New York from the vantage point of what cocreator and star Ben Sinclair has called “a very specific Brooklyn subset.” It’s the subset you would expect to have a bearded, bike-bound weed dealer known only as The Guy saved in their contacts, easily summoned by a text euphemistically asking him to “hang”—mostly affluent, mostly white, and uniformly progressive in their beliefs, if not their actions. Like Tray before his arrest, The Guy makes his living by selling illegal substances in and around Bed-Stuy (and Greenpoint, and Bushwick, and Ditmas Park, and …). There, the two men’s similarities begin and end.

Famously, High Maintenance began as a self-funded web series before graduating to Vimeo’s premium offerings and, finally, HBO. The most noticeable shifts in the show’s content, however, are Sinclair and Blichfeld’s attempts to expand its narrative reach along with its budget and platform. The HBO episodes—there have been 16 in total, including 10 from the recently concluded second season—are denser and longer than their predecessors. They also make much more of a visible effort to widen the High Maintenance world beyond the aforementioned subset. In its maturity, High Maintenance wants to include people its typical protagonists, and its real-world demographic, typically brush past without a second thought.

In the first HBO season, The Guy crossed paths with a Muslim college student who smokes weed to escape the pressures of school and family life (“Museebat”) and a can-collecting Chinese immigrant couple who don’t smoke weed at all (“Tick”). These episodes largely let their mission statement speak for itself, making an argument about whose stories are worth telling by positioning these less conventional stoner-show characters alongside loft-dwelling swingers and brownstone-owning day ravers.

The second season veers into more explicit variations on the same themes. “Globo,” the premiere, tracks the aftermath of some unspecified crisis that deliberately evokes the 2016 election through a cluster of mini-stories, the last of which follows a Latino waiter home after a night of cleaning up after agitated bubble-dwellers to pick up his son. A subsequent episode, “Namaste,” tackles gentrification head-on, following a Bed-Stuy realtor named Regine (Danielle Brooks) as she navigates the ethics of both her professional and personal lives. (Brooks is one of several Orange Is the New Black actors to cross over with High Maintenance; her castmate Yael Stone plays Beth, The Guy’s primary love interest.) Regine desperately wants to buy property for herself, but to do so, the Brooklyn native has to be at least partly complicit in the turnover of her neighborhood. At one point, Regine attempts to rent an apartment to The Guy, who she’s buying from in a defection from her relatively less well-supplied local dealer.

High Maintenance being High Maintenance, which dispatches most characters in 10 minutes or fewer, “Namaste” never takes a definite stance on the knotty issues it raises, content to end on a bittersweet note and move on. But other episodes build on its effort to adopt an outsider’s view on Brooklyn’s changes: “Derech” looks at Brooklyn’s still-thriving Hasidic community; “Fagin” calls out one Bushwick dweller’s self-absorption by following her visiting parents’ misadventures with their Airbnb. And in one of the series’ darkest vignettes to date, The Guy ends up assisting an elderly man living alone in a squalid apartment while the rest of Brooklyn blithely goes about its business outside.

Season 2 of High Maintenance’s HBO run was the first time that Blichfeld and Sinclair brought on outside writers. (Collaborators had directed a couple of early chapters of the web series, but this was also the first time Blichfeld and Sinclair outsourced behind-the-camera duties consistently.) Consequently, the tone sometimes felt noticeably off, possibly the inevitable fallout of a project so specific opening up its creative process. Some resolutions felt pat, like the collision between glammed-up club kids and Orthodox Jews that serves as the climax to “Derech,” and some scenes saccharine, like the subway car balloon toss instigated by the waiter’s son. The effect undercut the low-key naturalism that makes High Maintenance such a well-suited vehicle for empathetic storytelling in the first place, and let the show’s distance from its comfort zone show a little more clearly than it needs to.

High Maintenance and The Last O.G. share a laudable goal: to show Brooklyn for the paradox-prone place it really is, not the oversimplification it gets flattened into. They also wind up demonstrating what a difficult balance that is to strike. Despite its recent adjustments, High Maintenance remains firmly rooted in an undeniably privileged niche, while The Last O.G. relies a bit too heavily on misty-eyed reminiscences about days gone. But each series aims for something more novel than stale jokes about rising rents, online dating, or avocado toasts. The truism that the only constant in New York City is change is as true of Brooklyn as any other district. It’s only right that the quintessential Brooklyn show should change along with it.

Disclosure: HBO is an initial investor in The Ringer.