90s

1999 · RPG · PC / Steam

Planescape: Torment is one of the finest written RPGs ever made, a game that treats its medium as literature and pulls it off. Its combat drags and its systems can feel opaque, but the writing is so sharp and the world so strange that those problems shrink against everything else. If you want a game that asks hard questions and respects your intelligence enough to let you sit with the answers, this is it. Few RPGs have ever matched its ambition, and fewer still have delivered on it this completely.

1998 · Wes Anderson · 93 min · Comedy Drama

The film that launched Wes Anderson into the stratosphere and revived Bill Murray's career, a bittersweet comedy about obsession, reinvention, and the painful gap between who we are and who we want to be.

1995 · Amy Heckerling · 97 min · Comedy

Amy Heckerling's brilliant adaptation of Jane Austen's Emma into 90s Beverly Hills teen culture is both a perfect time capsule and a timeless comedy about growing up, looking beyond yourself, and the outfits along the way.

1999 · Mike Judge · 89 min · Comedy

Mike Judge's deadpan workplace comedy flopped at the box office and then became the most relatable film in every office worker's DVD collection, a quiet revenge fantasy about everything wrong with cubicle culture.

1999 · Gil Junger · 97 min · Romantic Comedy

A charming Shakespeare adaptation that gave Heath Ledger his breakout role and delivered a teen romance with genuine wit, real chemistry, and a poem scene that still makes people cry.

1994 · 11 Seasons · Cartoon Network / Adult Swim · Animated Talk Show / Surreal Comedy

Space Ghost Coast to Coast pioneered a form of comedy television that didn't exist before it and directly spawned the entire Adult Swim programming block. Its talk show format, built from repurposed 1960s Hanna-Barbera animation and bewildered celebrity guests, is wholly original and frequently hilarious. The show's quality varies wildly across eleven seasons and 110 episodes, but its best moments represent some of the most inventive comedy of the 1990s and 2000s. Its influence on adult animation and anti-comedy is difficult to overstate.

1990 · 6 Seasons · NBC · Comedy

The Fresh Prince of Bel-Air made Will Smith a star through a fish-out-of-water comedy that was funnier, more culturally significant, and more emotionally complex than its premise suggested. The class and cultural dynamics between Will and the Banks family provide comedy with genuine social observation, and the dramatic episodes, particularly the famous father scene, achieve an emotional power that transcends the sitcom form. The later seasons lose creative energy as the show became more of a vehicle for Smith's stardom than a comedy about culture clash.