Comedy is a genre that often brings joy and laughter, but there’s a unique subset that delights in inducing discomfort, cringe, and anxiety while still delivering those laughs. These are the comedies that ride the fine line between hilarity and squirm-in-your-seat tension. Here’s a look at the ten best anxiety-inducing comedies of all time:

1. The Royal Tenenbaums (2001) – Wes Anderson’s quirky family saga blends dry humor with profound personal turmoil, creating an offbeat comedic experience that has viewers laughing between moments of existential dread.

2. Uncut Gems (2019) – While not a comedy in the traditional sense, Adam Sandler’s frenetic performance in this high-stakes jewel trade story delivers a darkly comic vibe throughout an increasingly tense narrative.

3. Curb Your Enthusiasm (TV Series, 2000-Present) – Larry David’s semi-improvised series is famous for its cringe comedy. Watching David navigate through socially awkward situations creates a palpable sense of angst mixed with uncontrollable laughter.

4. The Lobster (2015) – Yorgos Lanthimos’ bleak and absurdistic view on relationships in a dystopian society flips from bizarrely funny to just plain bizarre, causing viewers to question whether they should be laughing or feeling disturbed.

5. After Hours (1985) – Martin Scorsese’s black comedy follows a man’s increasingly bizarre and anxiety-inducing misadventures through late-night Manhattan.

6. What We Do in the Shadows (2014) – This mockumentary about vampire roommates deals with the mundane aspects of everyday life — if you’re immortal and your daily routine involves avoiding sunlight and feasting on human blood. It induces both anxiety and belly laughs as it explores the humorous side of being undead outcasts in modern society.

7. Fargo (1996) – The Coen Brothers masterfully blend grisly crime with Minnesotan politeness, creating an unease dotted with quirky humor stemming from the dichotomy between violence and niceties.

8. Election (1999) – High school politics have never been more fraught with tension as a teacher observes an ambitious student’s obsessive run for class president in this satirical comedy.

9. In Bruges (2008) – Hitmen hiding out in Belgium might seem like an odd setup for comedy, but the film manages to produce genuine laughs amidst themes of guilt, mortality, and redemption.

10. Death at a Funeral (2007) – Both the British original and American remake take viewers through farcical misunderstandings and dark revelations at a funeral service that pivot between uncomfortable chuckles and outrageous humour.

Each film or show on this list plays upon our fears of social mishaps, personal failure, or bumbling through situations we can barely control — resulting in comedy that is uniquely tension-filled yet utterly unforgettable.