From ‘SNL’ To ‘Eastbound & Down’ — Jason Sudeikis’ Best A-Hole Characters

The reviews on Horrible Bosses 2 aren’t quite as promising as I’d hoped, but Jason Sudeikis, Charlie Day, and Jason Bateman had good chemistry in the first film, and I’m hoping that still holds true in the second. While Sudeikis might again be playing an underling that’s trying to get the upper hand on an asshole boss — or in this case, an asshole investor played by Christolph Waltz — he definitely has experience playing characters at the other end of the spectrum.

Some of Jason Sudeikis’ most memorable characters have been complete a-holes of varying degrees of douchiness. Here are five a-hole characters that Jason Sudeikis put his stamp on.

Gil, SNL

The “Around the Town” sketches paired Sudeikis with frequent SNL collaborator, Kristen Wiig as a news anchor and reporter with an uncanny knack for pouring “a big ol’ buckets of creep juice” on whoever she interviewed. It wasn’t one of Kristen Wiig’s most memorable characters, and truthfully, she comes off far more like an a-hole than Sudeikis, but it’s his lack of any empathy whatsoever every time she makes a fool of herself that lands this character on the list.

Eric, A Good Old Fashioned Orgy

Make no mistake about it, Eric of the 2011 comedy, A Good Old Fashioned Orgy, is definitely an asshole. Sure, he’s probably a fun guy to hang out with because he throws killer parties like “the white trash bash,” but he does so with complete disregard for his neighbors and family’s home. By the end of the movie, Eric has learned nothing except that he can convince his friends to bang and that Labor Day weekend is superior to Memorial Day weekend for having orgies.

David Clark, We’re the Millers

David Clark lands Jason Sudeikis’ in the A-Hole Hall of Fame for two reasons: he’s a drug dealer, which generally disqualifies him from the “solid guy” category, and he has no problem using others to save his ass and make a profit. It’s only after feeling guilty because of TLC’s “Waterfalls” — man, does that song make one think about life — that he decides not to abandon his fake family.

DJ Supersoak, SNL

Next to the Two A-holes from SNL, DJ Supersoak is by far the most annoying asshole Jason Sudekis has played. He’s generally harmless, but he’s likely passed out in the sun at one too many Gatherings of the Juggalos and now has the personality of a rejected Faygo flavor. I’m not even sure he’s sad that Ass Dan is dead.

Shane, Eastbound and Down

If DJ Supersoak is as charming as a Faygo flavor reject, Shane has all the charisma of a pair of TruckNutz. This compliments Kenny Powers perfectly, providing an injection of assholery that was almost too much for the show to handle. This probably explains why Shane’s identical twin brother Cole was such an uptight dork. R.I.P. Youngblood.

One of Two A-holes, SNL

This was one of Jason Sudeikis and Kristen Wiig’s earliest collaborations and one of their best while on SNL. We never learn their names in the sketch, just that babe can barely pull her eyes away from her cell phone and nobody makes gum chewing more infuriating than Jason Sudeikis’ popped collar a-hole character.