There's a reason this one season show continues to hold its status as a cult classic. Freaks and Geeks is hilarious and extremely heartfelt look at high school's trials and tribulations, feeling fresh from its first viewing and every subsequent re-watch that will inevitably follow. It's also a kick to see the baby-faced James Franco, Seth Rogan, Linda Cardellini, and Jason Segel in some of their earliest roles. (Amazon Prime)
Tia and Tamera Mowry star in Sister, Sister as twins separated by birth, only to reunite as teens when they meet by chance at the mall. Their families obviously have no choice but to move in together, resulting in the most delightful mayhem. Who doesn't love twin reunion fodder? Plus, Jackée Harry's performance as Lisa Landry is comedic gold. (Netflix)
The Disney Channel reached programming apotheosis with Lizzie McGuire, which ended up being one of the most beloved cultural products of the aughts. The titular Lizzie is awkward and endearing and the show has a steady moral compass that's never overbearing. There's also her frenzied animated inner thoughts that feel oddly relatable, even when you're well past your middle school years. (Disney+)
Degrassi tried to "go there" with dark issues like its wild child contemporary Skins, but it ended up more of a campy high school romp than anything. Look no further than Drake's performance as Jimmy. (Amazon Prime)
The dark horse of this list is, of course, Daria. The animated series was snarky and cerebral with just the right amount of gloom, making it a seminal satire about suburban teenage life. Daria and her best friend Jane can't be bothered with their high school's social hierarchy, parental advice, or anything really. It's the best PR misanthropy ever got. (Hulu, MTV)
High school life will always suck to some degree, especially if you're navigating armed British officers in Northern Ireland in the 90s. Enter Derry Girls, the chaotic sitcom that brings you into that exact historical hypothetical. Turn on subtitles for this one. (Netflix)
Perhaps the most All-American sitcom on this list, Boy Meets World is also rare in how it follows its characters as they mature from awkward middle schoolers all the way into college students (under the watchful eye of beloved teacher and neighbor Mr. Feeny), with plenty of cringe coming-of-age moments along the way. (Disney+)
Two words: Carlton Banks. The Fresh Prince may have given us Will Smith, but "the Carlton dance" will live on forever. (HBO Max)