It probably took some deep breaths, but hopefully by now you’ve come to terms with the news that Jon Stewart is ditching us to direct his first feature this summer. Rosewater, about a Canadian-Iranian journalist who was thrown in a Tehran prison in 2009, will be Stewart’s directorial debut, but it won’t be his first time on a movie set. Before taking over The Daily Show in 1999, Stewart was making out with Gillian Anderson and strangling Elijah Wood all over big screens near you. With only one more week of Daily Shows left before John Oliver takes over until September, we’re revisiting some of Stewart’s most Oscar-robbed performances.
The Nanny – 1997
The terrible quality of this video can’t take away from the topnotch quality of a pickup line like, “Which one of you ordered the short Jew?” Here’s Stewart playing a rich doctor who buys Fran Drescher lobster.

NewsRadio – 1997
Stewart dweebs it up as Andy Dick’s fake twin brother.

Half Baked – 1998
Behold Stewart’s passable performance as a really, really stoned person in Half Baked. Bet there’s tons of “enhancement smokers” watching The Daily Show every night.

The Faculty – 1998
Stewart strangles Elijah Wood and gets his fingers cut off by Josh Harnett before being gauged in the eye with a pen. Still, the scariest thing about this clip is his goatee.

Playing by Heart – 1998
Sensual Stewart makes out with sensual Gillian Anderson by a sensual roaring fire.

Big Daddy – 1999
Adam Sandler fucks up Stewart’s proposal to Leslie Mann.

Jay and Silent Bob Strike Back – 2001
Having already established himself as a reliable newsman on The Daily Show, Stewart investigates the mysterious and dangerous C.L.I.T organization.

Death to Smoochy – 2002
Death to Smoochy was Stewart’s last appearance in live-action movie where he wasn’t playing himself. Watch him scream at Robin Williams in a car with what’s maybe a Brooklyn accent.