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If I could turn back time...
Before starring in movies and shows like Napoleon Dynamite and Veronica Mars, Tina Majorino was a bonafide child star in the '90s. It seemed like at least 40% of the time I turned on my TV, there she was, in movies like When a Man Loves a Woman, Waterworld, and Corrina, Corrina. Between this and her soft-spoken, subtle approach to acting, I think she would've been a great pick for Eleven.
Not to typecast, but...come on. John Francis Daley is probably best known for playing Sam Weir in Freaks and Geeks, and Sam and Mike Wheeler are basically the same person — they both have older sisters who are annoyed with them 98% of the time; they both play Dungeons & Dragons; and they even look similar.
Bug Hall was another actor I saw all over my TV in the '90s, in kids movies like The Big Green, Honey, We Shrunk Ourselves, and his film debut, The Little Rascals, for which he sported the iconic cowlick to play Alfalfa. Between his big puppy eyes and bowl cut, I could definitely see him as Will Byers.
Josh Peck was definitely more of an aughts child star — his first movie, Snow Day, came out in 2000 — but he's the right age to have played a tween in the '90s, and had the right energy to play the funny, and sometimes slightly manic, Dustin Henderson.
The late Lee Thompson Young was literally the ultimate action hero (or at least he played a kid playing one on TV), and you know if anyone could hit a Demogorgon square in the "face" with a slingshot, it's Jett Jackson. I think he would've been perfect to play the smooth-talking, (sometimes overly) confident Lucas Sinclair.
I'll admit that while Michelle Trachtenberg did a lot in the '90s, I know her best from Buffy the Vampire Slayer. In my opinion, there are a lot of similarities between Dawn Summers and Max Mayfield, from their unwanted younger sibling vibes to the sass they're able to easily lob at anyone and everyone. Plus, Trachtenberg proved she could hold her own against onscreen monsters more than once on Buffy.
Max is far from the only one supplying plenty of sass on Stranger Things, and as a staple of '90s television (I'm pretty sure she was in at least one episode of nearly every show I watched back then), I think Kyla Pratt could have nailed Erica Sinclair's signature side-eye.
It's hard not to notice a resemblance between Natalia Dyer and Christina Ricci, who, let's face it, absolutely ruled the '90s. She also clearly had (and still has) a propensity for the strange and spooky, having starred in the Addams Family movies, Casper, and Sleepy Hollow. I think she would have been a perfect Nancy Wheeler
Speaking of '90s teen royalty, Devon Sawa was great at playing the cocky, charming, pretty boy, and based on his performance in Idle Hands, he can seamlessly transition into a panicked demon-fighter willing to sacrifice his body for the cause. Plus, I for one would love to see him and Christina Ricci reunited once again after appearing in Casper and Now and Then together.
Elijah Wood generally skewed pretty wholesome in the '90s, but his character in The Faculty — an unpopular high school loner with a camera — was just Jonathan Byers all over. He even had creep shots of his crush tacked up on his bedroom wall. Plus, it'd be yet another reunion between Christina Ricci and one of her onscreen beaus, after the two appeared in The Ice Storm together.
Like a lot of the others on this list, Marla Sokoloff popped up on my TV time and time again during the '90s, and she was great at playing the snarky BFF — and Robin Buckley is nothing if not a snarky BFF. If anyone could go head-to-head with Steve Harrington and keep him extremely humble, it'd be Sokoloff.