Aubrey Plaza has a specific brand of chaos. You know the one. It’s that deadpan, slightly terrifying stare that makes you wonder if she’s joking or planning your demise. But back in 2013, before she was the reigning queen of indie prestige and The White Lotus sarcasm, she starred in a movie that a lot of people just sort of... missed. The To Do List is a weird, sweaty, uncomfortable, and deeply funny time capsule. It’s a 1993 period piece made in the early 2010s that feels like it could never be made today.
The premise is simple. Maybe too simple. Brandy Klark is a Valedictorian who is "math-letes" levels of nerdy. She realizes she’s heading to college with zero "life experience," which is a polite way of saying she’s never done anything sexual. So, she makes a list. A literal, handwritten, color-coded list of sexual milestones to hit before campus orientation.
It’s gross. It’s honest. It’s kind of a masterpiece of the "coming-of-age" genre that usually belongs to the boys.
Why The To Do List Flipped the Script on Teen Comedies
For decades, we’ve been fed a steady diet of movies where teenage boys are the ones desperately trying to lose their virginity. Think American Pie. Think Superbad. The girls in those movies are usually the "goal" or the "prize." They are objects to be pursued. The To Do List takes that entire trope and tosses it out a window. Brandy isn’t looking for love. Honestly, she isn’t even really looking for pleasure at first. She’s looking for efficiency. She treats sex like a biology project.
Writer-director Maggie Carey (who was actually married to Bill Hader at the time) based a lot of this on her own upbringing in Boise, Idaho. That’s probably why it feels so grounded despite the absurdity. The movie doesn't judge Brandy for being calculated. It doesn't shame her for wanting to check "handjob" off a list between reading assignments.
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There’s a specific scene involving a dry-erase board that is so cringeworthy you might want to turn it off. Don't. It’s the point. The film captures that specific, agonizing awkwardness of being eighteen and having absolutely no idea what you’re doing with your own body. It’s the anti-Notebook. There are no rain-soaked kisses here; there is mostly just chlorine, bad sunscreen, and fumbled attempts at intimacy.
A Cast That Was Low-Key Legendary
If you look at the call sheet for this movie today, it’s actually insane. It’s a "who’s who" of comedy royalty before they hit their peak.
- Bill Hader plays the local pool manager, and he is essentially playing a version of every burnout boss you’ve ever had.
- Rachel Bilson is the older, "cooler" sister who provides terrible advice.
- Donald Glover shows up. Yes, Childish Gambino himself.
- Andy Samberg plays a grungy van-dwelling rocker named Van.
- Connie Britton and Clark Gregg play the parents. Imagine Coach Taylor's wife and Agent Coulson dealing with a daughter’s sexual bucket list.
Watching it now feels like looking at a high school yearbook of the funniest people in Hollywood. Everyone is playing it fast and loose. The chemistry between Plaza and Johnny Simmons (who plays the "nice guy" Cameron) is genuinely sweet, while the tension between her and Scott Porter (the "hot guy" Rusty Waters) is purposefully, hilariously shallow.
The 1993 Aesthetic: More Than Just Nostalgia
The movie is set in 1993. This wasn't just a random choice. Carey wanted to set it in a time before smartphones and high-speed internet. There’s something fundamentally different about a teenager looking for sexual information in a physical encyclopedia or a smuggled Cosmopolitan magazine versus just Googling it.
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The stakes feel higher.
The world was smaller. If you did something embarrassing at the local community pool in 1993, it stayed at the pool. It didn't end up on TikTok. This allows Brandy to be a total disaster in a way that feels safe for the audience. We can laugh at her because we know her mistakes aren't being archived for eternity on a server in Virginia.
Also, the soundtrack is a banger. You’ve got Salt-N-Pepa, 24-7 Spyz, and Naughty by Nature. It nails that transitional period between 80s hair metal leftovers and the rise of grunge and hip-hop.
Is The To Do List Actually "Feminist"?
People debate this. Some critics at the time felt the movie was just "Superbad with a girl," as if that’s a bad thing. But there is a nuance to Brandy’s journey. She starts the movie thinking she can control sex through logic. She thinks she can master it like she mastered AP Calculus.
By the end, she realizes—shocker—that emotions and human connection are messy.
The "feminist" angle isn't that she becomes a sexual goddess. It’s that she’s allowed to be as crude, selfish, and goal-oriented as any male lead. She doesn't have to be a "cool girl." She’s allowed to be a dork. She’s allowed to fail. In the world of cinema, letting a woman be a total, unpolished "try-hard" is a radical act.
What People Get Wrong About the Ending
A lot of viewers wanted a traditional rom-com ending. They wanted her to realize the "nice guy" was there all along and ride off into the sunset. But The To Do List doesn't really do that. It stays true to the character. Brandy is headed to college. She’s eighteen. The movie understands that your first sexual experiences aren't usually the beginning of a lifelong romance. They are just... experiences.
They are entries on a list.
How to Revisit the Film in 2026
If you’re going to watch it today, you have to lean into the discomfort. It’s a "cringe comedy" in the truest sense. It’s also a reminder of how much the landscape of teen movies has changed. Today, we have Sex Education and Euphoria, which are great but often feel very heavy or hyper-stylized.
The To Do List is just a comedy. It wants to make you laugh at how gross humans are.
Actionable Takeaways for Movie Buffs
- Watch for the Background Gags: Bill Hader’s character, Willy, is constantly doing something weird in the background of the pool scenes. His improvisation is top-tier.
- Check the Wardrobe: The costume design is brutally accurate to the early 90s. Note the specific cut of the high-waisted shorts and the oversized t-shirts. It’s not "Halloween costume" 90s; it’s "real-life thrift store" 90s.
- Compare to "Diary of a Teenage Girl": If you want a double feature, watch this alongside Diary of a Teenage Girl. One is a broad comedy, one is a serious drama, but both deal with the agency of young women and their sexual awakenings in a way that feels authentic to their respective eras.
- Look for the Cameos: Aside from the main cast, keep an eye out for Christopher Mintz-Plasse (McLovin) and Alia Shawkat.
The movie holds up because it doesn't try to be anything other than what it is: a raunchy, honest, slightly gross, and incredibly funny look at a girl trying to figure herself out. It reminds us that being a teenager is mostly just a series of awkward encounters held together by a desire to be "normal."
If you've ever felt like you were behind the curve, or if you've ever made a list to solve a problem that can't be solved with logic, this movie is for you. Go find it on streaming. It’s better than you remember, and it’s weirder than you think.
Next Steps for Your Watchlist
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To get the most out of this era of comedy, look into the filmography of the The Lonely Island members who produced this, or track down Maggie Carey's interviews about the production. It’ll give you a whole new appreciation for the "Boise style" of humor that defines the film's DNA. Check your local streaming platforms like Max or Hulu, as it frequently rotates through their libraries.