It's initially tough to tell if a comedy starring two 30-year-olds portraying middle schoolers will actually work, but about five minutes into the first episode of PEN15, it's clear that they've nailed it.
Affectionately categorized as a "traumedy," the show focuses on two best friends, Maya Ishii-Peters (Maya Erskine) and Anna Kone (Anna Konkle), as they head off for their first year of middle school. The pair is classically uncool in the best sense, with Maya showing up on the first day with an accidental bowl haircut and a rolling backpack at her side. Middle school is a bit of a culture shock for the two, who try their best to get in with the cool kids but almost always get swindled in some way.
The first season is almost entirely devoted to the more classic rite-of-passage, middle school moments, which includes Maya and Anna creating their AIM accounts, forcing themselves to play with their dolls but getting sick of it, and screwing up a drum solo in front of the entire school. As a side note: an absolute must-watch is "Community Service" from Season 1, which just might be the funniest episode of the entire show.