A Millennial Nostalgia Watchlist

As a millennial, it’s a little weird seeing the pop culture of each stage of my childhood rebooted. In the next year, we’re getting a Super Mario Brothers movie, a Nintendo-themed world at Universal Studios, a Janet Jackson tour, a Blink 182 tour, and That 90s Show just dropped, a follow-up to That 70s Show. We are now as far out from the 90s as the initial That 70s Show was from the 80s.

While the realization that I’m old has hit me like the death of a Tamagotchi, I started to reflect on the films and TV shows that shaped me – and the ones that my fellow millennials have made about our generation. We have been through a lot: 9/11 when we were still in grade school, a Great Recession just as many of us were trying to find jobs, the one-two punch of Trump and Covid just as we were finding our footing.

So it’s not too surprising we are often nostalgic for the Y2K era and its wake. In honor of That 90s Show, here’s a Watercooler Guide to 9 others shows that have resonated with and helped shaped us.

The Early Years

Pen15

What it’s about: Creators Maya Erskine and Anna Konkle were in their 30s when they played awkward middle schoolers, surrounded by actual middle schoolers, in this hilariously cringe-y comedy. Inspired by their own 7th grade lives as outcasts in the early 2000s, each episode focuses on universal tween experiences such as crushes while throwing in Y2K specifics, like creating the perfect AIM name and worshiping the Spice Girls.

Why it resonates with Millennials: Like Erskine and Konkle, I too was a dorky tween who tried chatting with my crushes on AIM. While my own middle school experiences were quite different, it’s hard not to watch Pen15 and laugh at its absurd and familiar storylines. Who doesn’t remember that one friend who introduced you to swearing or your first time shaving?  Yet Pen15 goes deeper than its silly premise, and it doesn’t shy away from the blatant homophobia, casual racism, and hypersexualization of women and girls that ran rampant during the early 2000s — which can make you grateful to have “grown up.”

              Where to watch Pen15: Hulu

The Teenage Years

Degrassi: The Next Generation

What it’s about: A direct follow-up to Degrassi Junior High and Degrassi High, Degrassi: The Next Generation followed a group of junior high student at the fictional Canadian Degrassi Community School as they faced a different issue every week, from bullying to drugs to pregnancy to school shootings.

Why it resonates with Millennials: Also known as the show that introduced the world to Drake, there was a certain camp to Degrassi that made it great. Every week my friend and I looked forward to seeing what type of afterschool special awaited us. We lived for the characters’ Canadian accents and over-the-top outfits (Manny parading through school in a thong is iconic). But as silly as Degrassi could be, it was still groundbreaking. Actual teenagers played teenage characters, and sensitive topics — like a school shooting — were handled delicately. The series also featured fully dimensional LGBTQ+ characters long before any other teen show.

Where to watch Degrassi: The Next Generation: HBO Max

Napoleon Dynamite 

What it’s about: Napoleon Dynamite (Jon Heder) is a geeky high school student living in small town Idaho. Throughout the film, he tries to woo a fellow member of the sign language club, helps his friend run for class president, get his first job at the Chicken Coup, and deal with his clueless brother and boorish uncle.

Why it resonates with Millennials: It’s difficult to pinpoint why millennials loved Napoleon Dynamite so much. It might have been its deadpan PG humor, quotable lines (“your mom goes to college!”), or its unlikely hero. Despite his oversized glasses, untamed hair, and permanent slack jaw, Napoleon is weirdly confident and never seems to take himself too seriously. He’ll dance his own version of a dance in front of the whole school or draw a horrifying picture to get a girl’s attention. He tows his brother on roller skates behind his bike, and makes homemade “Vote for Pedro” shirts for his friends campaign — shirts that have since become Urban Outfitter and Halloween costume-worthy staples, almost two decades after the film premiered. Jon Heder later reflected on his most famous role: “Everybody knew a guy like Napoleon growing up. I think there was just something about it that connected a lot of people.”

          Where to watch Napoleon Dynamite: HBO Max

Mean Girls

What it’s about: Cady (Lindsay Lohan) grew up in Africa where she was home schooled. When her parents move to suburban Chicago, she goes to “real” school for the first time, where she’s overwhelmed by the various rules, cliques, and drama. After being adopted by “the plastics,” Cady teams up with her new friends Janice (Lizzy Caplan) and Damien (Daniel Franzese) to end their reign of terror.

Why it resonates with Millennials: One-liners from Mean Girls are now a part of our daily lexicon. If you tell someone that on Wednesdays, we wear pink, they’ll most likely know exactly what you’re referring to. Mean Girls was Tina Fey’s opus – she perfectly skewered the “mean girl” mentality prevalent in high schools while satirizing the unrealistic beauty standards teen girls were held to. While Gen Zers seem to love Mean Girls, this high-school classic belongs to millennials. From the early 2000s fashion to the ridiculous slang, Mean Girls continues to be fetch.

       Where to watch Mean Girls: Pluto TV

Lady Bird

What it’s about: Set in the early 2000s, Lady Bird follows Christine (Saoirse Ronan), a senior at a Catholic high school in Sacramento from the wrong side of the tracks who has big dreams of living a more exciting, more glamorous life “where culture is.” So she begins applying to colleges on the east coast, creating new tensions in her already strained mother-daughter relationship.

Why it resonates with Millennials:  Loosely based on writer-director Greta Gerwig’s own life, Lady Bird was one of the first coming-of-age movies made by a millennial woman — one with big stars like Ronan and Timothy Chalamet. Gerwig infuses the characters with so many particulars, she perfectly captures a time and a turning point in life. My sister and I both had the same fiery spirit as Christine, yet we were also vulnerable and had no clue what we were doing. Ronan dons messy dyed red hair and thrift shop bracelets, both staples that either I or one of my close friends had. And bringing it all home for everyone is the soundtrack of moody music of the era (hello Alannis and Dave Matthews Band). “We’re afraid of what the future will bring,” a priest says to Lady Bird, encapsulating a the fears of every post-9/11 kid. In Gerwig’s case, it’s uplifting to see that all of Lady Birds dreams came true.

       Where to watch Lady Bird: Showtime

The Twenties

Ramy

What it’s about: Ramy follows its titular character, a Millennial living in suburban New Jersey as he tries to become a better Muslim. The son of Egyptian immigrants, Ramy makes plenty of mistakes on the way – but he does grow, little by little. The series also follows his family and friends as they navigate life as Muslims and Arabs in current-day America.

Why it resonates with Millennials: I am a little biased when it comes to Ramy because I am half-Egyptian and my father is Muslim. I never saw Egyptians – let alone Muslims – portrayed as anything other than terrorists growing up. When I first saw Ramy, I was amazed to find a series that reflected my own community. While some of the themes explored are unique to Arabs and Muslims, others are universal. Finding the right partner, setting boundaries with your parents, and trying to be a better person are issues we all deal with, regardless of one’s faith.

        Where to watch it: Hulu

You’re the Worst

What it’s about: Two hot messes, brash Jimmy (Chris Geere) and self-destructive Gretchen (Aya Cash) decide to attempt a relationship after meeting a wedding. Jimmy’s friend Edgar (Desmin Borges) comes to terms with his PTSD, while Gretchen’s bestie Lindsay (Kether Donohue) debates getting a divorce.

Why it resonates with Millennials: You’re the Worst is a dark comedy that handled its darker subjects well, and Jimmy and Gretchen’s relationship thrives on its imperfections. It was one of the first shows to accurately portray what living with depression is like. Edgar’s PTSD isn’t treated as his sole character trait; it’s simply a part of who he is. For a generation breaking the stigma around mental health, the characters are a refreshing change from traditional sitcoms.

         Where to watch it: Hulu

(500) Days of Summer

What it’s about: When Tom (Joseph Gordon-Levitt) first meets Summer (Zooey Deschanel), he’s immediately smitten. They embark on what Tom considers to be a relationship – although Summer tells Tom she does not want a relationship. After Summer breaks up with him, Tom reflects on where he thinks the relationship went wrong.

Why it resonates with Millennials: 500 Days of Summer isn’t exactly a rom-com, it’s more a coming-of-age story that takes a realistic look at romance. Summer flat out tells Tom she doesn’t believe in marriage after watching her own parents divorce. Yet he’s a hopeful romantic, and continues to pursue a serious relationship with her, not realizing that he isn’t actually in love with Summer, he’s in lust with her — and in love with his idealized version of her. He doesn’t realize how wrong they were for each other until he later reflects on the relationship. Millennials (and others) grew up with the idea of lust and love as one in the same, thanks to numerous rom-coms. But 500 Days of Summer was one of the first movies with millennial characters who are forced to face the fact there’s a big distinction.

                Where to watch it: HBO Max

The Thirties

Insecure

What it’s about:  Facing 30, Los Angeleno Issa is dissatisfied with both her nonprofit job and her relationship. She relies on her bestie, Molly (Yvonne Orji), a successful lawyer with her own relationship problems, as her confidante. Marriage and kids aren’t the focus of Molly and Issa’s lives; they’re two powerful Black women ready to chart their own course. As the series went on, both Issa and Molly decide to make significant changes and improve their lives. But change is not as easy as it seems.

Why it resonates with Millennials:  From trying to find the right job and career footing in your 30s to dating mishaps to navigating the intersectionality between race and gender, Insecure was often relatable for all millennials, but especially for its realistic portrait of life for a lot of Black millennials. Many of the stories were pulled from Rae’s and the writers’ own experiences. There were no big “plights” the characters had to overcome, a refreshing change from other shows centered around Black characters. While race relations are a big theme in the series, it’s not heavy handed. For Issa and her friends, it’s more about the everyday challenges, and they quickly learn there is no one way to go about dealing with your problems…except to infuse them with plenty of humor.

       Where to watch Insecure: HBO Max

New Girl 

What it’s about: After breaking up with her boyfriend, middle school teacher Jessica Day (Zooey Deschanel) moves in with three men. She has a lot of quirks, like making weird voices and micromanaging their collective loft life, but her roommates come to love her. A more realistic sitcom about 20 and 30 somethings than the Gen-X hit Friends, New Girl’s brings the backdrop of aughts and point of view of the next generation down, and instead of being across the hall, they’re all together in one big warehouse-y loft somewhere in LA.

Why it resonates with Millennials:  To older generations, living with roommates in your 30s may seem odd. For millennials, it’s quite normal – especially in larger cities. While New Girl has its silly moments (like the roomies’ inexplicable drinking game, True American), it never shies away from reality. Jessica get laid off from her job, her roommate Winston struggles to find the right career, and all of the characters have numerous dating woes. Yet even through the rough spots and as their lives change, they are always there for each other…just like the refrain of that Friends song. The idea that you don’t have to have it all figured out by a certain age is comforting for my generation, considering we’re doing things a bit differently. Unlike boomers, a majority of millennials postponed marriage and have yet to buy a house by 30. The characters of New Girl reassured us that this was okay – and it’s okay to play ridiculous drinking games, even into your 30s.

         Where to watch it:  Netflix   

Search for Watercooler Picks
Search
Generic filters
Exact matches only
Search in title
Search in content
Filter by Section
Watercooler Picks
Community Picks

Now Percolating

Trending Across the Site
RECENT ARTICLES

Looking for something new to watch?

Our advanced search engine can help you find fresh suggestions based on mood, interest, theme, and more.

BINGE VIEWERS CLUB

Find your people! Sign up for fresh recommendations, invites to events, and a chance to be featured on our site.

Start a watercooler conversation:

Leave a Comment

Your email address will not be published. Required fields are marked *

Newsletter signup

Scroll to Top