How does Jason Sudeikis keep bagging such hot actresses? In 2011 we obsessed over his relationship with January Jones – mostly because he was rumored to be her babydaddy — and now the SNL star has rounded out the year with a new relationship: He and Olivia Wilde were spotted in NYC on New Year’s Day getting coffee and kissing.
The two have been out and about several times over the last few days; they were actually outed at a Kansas University basketball game late last week, when the official KU Twitter account tweeted a photo of them. The fact that that is a tried-and-true rom-com trope is even funnier since both were known for raunchy comedies like Horrible Bosses (him) and The Change-Up (her) in 2011.
But again, the question comes down to how the unassuming Jason has had a bevy of beautiful ladies on his arm. After splitting with his wife of six years, 30 Rock writer Kay Cannon, Jason was rumored to be hooking up with his Horrible Bosses co-star Jennifer Aniston. Though he’s jokingly denied it, he’s never flat-out said that they weren’t involved.
So where does this attraction come from? A lot of people don’t find him conventionally handsome, and as his 2010 Vanity Fair profile points out, it’s “rare terrain” for tabloids to obsess over a comedian’s sex life: There are certainly exceptions, but for the most part we aren’t interested in speculating about whom our comics are diddling. You could read every gossip site on the Internet and you’ll never find a story that asks, “Which hottie from Grey’s Anatomy is Louis C.K. sleeping with this week?”
So maybe it’s that he’s more approachable than the men (Ashton Kutcher, Justin Theroux, Brad Pitt) that his ladies have been involved with. Maybe it’s his bevy of celebrity impressions. Or maybe it’s his breakdancing skills on the SNL skit “What Up With That”:
Go on with your bad self, Jason.