With Tim Robinson of *I Think You Should Leave* landing his first leading role in a film — portraying the well-meaning but awkward Craig in Andrew DeYoung’s *Friendship* — we thought it was the perfect time to celebrate the absurd comedic brilliance he's become known for. There's no doubt that Robinson has carved out a unique space in the world of cringe comedy, delivering unforgettable moments that are equal parts awkward and hilarious.
Even if you haven’t yet tuned into *I Think You Should Leave*, the wildly surreal and socially uncomfortable sketch show now streaming on Netflix with three full seasons, you’ve definitely come across its viral moments online. From bizarre pranks gone wrong to inexplicable vehicle mishaps, Robinson’s sketches have become cultural touchstones that keep fans quoting lines for days.
Below, we’ve rounded up some of Tim Robinson’s most unforgettable and awkwardly brilliant sketches — from wild zip-line disasters to unexpected WeinerMobile appearances — each one a testament to his genius for turning discomfort into comedy gold.
***Warning: The following content contains mature themes and humor. Viewer discretion is advised.*