The first episode of Benny Skinner’s new series Overcompensating is bookended by the Britney Spears song "Lucky". Released in 2000, the pop masterpiece was a millennial anthem that we listened to in our bedrooms on Sony Dream Machines and at lacklustre school discos, which is to say it perfectly invokes what early millennial teenagehood felt like. Overcompensating uses this feeling as a springboard to launch a thousand millennial pop culture references, a backdrop to a poignant look at themes such as sense of self and sexuality in the early aughts. It’s a journey of self discovery—with some dabbing thrown in.

Following Skinner’s jock/valedictorian/homecoming king eponymous protagonist, the series, produced by Amazon Studios and A24, focuses on that painfully self-conscious transition from home to college life in an era which can be loosely pinpointed as around 2010 (although there are some confusing anachronisms). It’s based on Skinner’s own life and college experience at that time; he attended Georgetown University in D.C.—the inspiration for Yates, the fictional college where Overcompensating plays out.

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Skinner has been open about the fact he struggled with fitting in growing up. He didn’t come out until he was 20, and spent his early college life moving between social groups. On the show we watch Benny try and prove himself as a ‘f**k boy’ when he knows he actually has feelings for fellow freshman, Miles. We see the internal struggles Benny battles, realising that being ‘perfect’ for everyone else is no longer serving him. The title of the show becomes more apt with every code-switch he performs.

An easy, very funny and heartwarming watch, it’s hardly surprising that the series has shot to the top of Amazon Prime’s most watched shows, hitting number one in the US this week. Skinner has already built a huge fanbase on social media where he’s known as Benny Drama and has been acting out sketches for years, parodying the Kardashians, Gossip Girl, Shawn Mendes and nurturing his own characters like Jenny the Hairdresser and Cooper the Gen Z intern.

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There is clearly a big audience for this indulgence in recent history, then. While we have been inundated with a huge amount of Y2K nostalgia in the past couple of years, there is something about this specific, slightly later era which feels less charted. It’s a not-too-long-ago world which came just before fast-moving aesthetic trends took over our feeds, a world before Ozempic, a world before a Trump-presidency. Overcompensating taps into that early world of social media perfectly with references to cringey hashtags (‘here’s to nights we won’t remember with friends we’ll never forget’) and awkward selfies.

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Some have queried the fact that Skinner, 31, is playing himself, whilst his co-stars Mary Beth Barone, who plays his sister, is 34, and Adam DiMarco, who plays Peter, is 35. This, however, is in itself a part of the show’s charm. It’s a call back to the millennial teen movies we obsessed over: Freddie Prinze Jr was 25 when he played a teenager in She’s All That, Selma Blair was 27 when she played 15-year-old Cecile in Cruel Intentions, and Rachel McAdams was 26 when she played Regina George in Mean Girls. Acting below age range is in our culture, we feel safe there (probably a part of the reason why comedy series PEN15, in which 30-year-old comedians Maya Erskine and Anna Konkle play their teenage selves was such a hit).

Skinner himself has acknowledged that there is a strong nineties teen movie inspo at play: "It’s like American Pie, but what if we made it very gay?!” Skinner said in an interview with Harper’s BAZAAR. "I wanted to make something that had those late ’90s, Y2K nostalgic influences, where all the characters sexualise themselves in ways that are clunky."

Millennials have come under fire in recent times for just about everything, from the partings in their hair (side parts are a big no-no) to their weddings (Converse/photo booths/hay bales are all off the inspo boards now) to their socks. Having existed in a pre-TikTok world is to have been nothing but cringe, if Gen Z is to be believed.

Overcompensating provides a nice counter to this: It doesn’t poke at millennial culture, in fact it makes parts of millennial culture feel quite safe and sweet. We didn’t know what we were doing on social media, or care that we only got seven likes, and isn’t that better than trying too hard? We had 76 followers on Instagram and posted blurry photos of a drink on a bar and thought we were arty. Yes there was dabbing, people referenced Glee (Benny and his college best friend Carmen bond over their love of the show) and everyone wanted to be a DJ, but we had some sense of hope. It’s quite nice to remember a time before the doom scroll existed, however awkward we were. And being reminded that you know all the lyrics to Nicki Minaj’s rap in "Super Bass" is a life-affirming millennial moment, provided by an awkward Benny trying to impress a fraternity who’d rather be listening to 'Like A G6'. The hold Twilight had on pop culture comes flooding back when Grace dresses up as Alice Cullen for Halloween.

The music is a huge part of the show’s unique power. With Charli XCX as an exec producer (she’s a close friend of Skinner and his partner Terrence O’Connor) the soundtrack was always going to be good, although it is via her songs that many of the anachronisms lie; for example when Charli plays a gig at Yates she performs 'Boys' which wasn’t released til 2017, while 'Party 4 U', released in 2020 but trending again currently, plays over the end credits. When Grace performs My Chemical Romance’s 'Welcome to the Black Parade', it unearths the former emo in all of us.

Overcompensating celebrates—and side-eyes—everything which made being young in the time of the second Obama term memorable. Of course things weren’t perfect, and slut-shaming is a main theme of the show. But it demonstrates such a clever use of cultural references to make Benny’s inner turmoil about his sexuality all the more poignant.

Late Millennial culture, even the cringey parts, might just be having a comeback. And we’re all for it.

This article was first seen on ELLE US.