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Photography by Mr Alexei Hay | Styling by Mr Grant Woolhead
Words by Ms Hadley Freeman

While Mr Jason Sudeikis insists that he has "never had any kind of career plan", happily going "from vine to vine, taking whatever comes", he does have one absolutely non-negotiable goal. "I'm going to win an Oscar at 50 - definitely," he announces, his already deep voice dropping an extra half-octave for emphasis. "And I'm going to die at 49 and a half to ensure I get that Oscar. I need to die as close to the Oscar ceremony as possible so I'm the last person in the montage of dead people they show every year. That's the best spot, you know."

Has he planned how he'll die as precisely as when? "Oh definitely. It'll be in a hot tub, with my entire head squeezed into a jet. The photos are going to be hilarious. Man, I really hope the internet sticks around so people can reference this article in my obituaries and see that what sounds like a joke was actually amazingly prescient."

Aside from Jacuzzi-based death and a posthumous Oscar, Mr Sudeikis' career path has not been quite as happenstance as he might suggest. In fact, it verges on the traditional, having started out at renowned comedy theatre The Second City in Chicago before getting hired on Saturday Night Live and then moving easily into films. It's the exact same path trod by Mr Dan Aykroyd, Mr Chris Farley and Ms Tina Fey, to name a few. Having starred in two successful films last year (Hall Pass with Mr Owen Wilson and Horrible Bosses with Mr Jason Bateman), as well as making a high-profile appearance in the critically fêted TV show Eastbound and Down, Mr Sudeikis' image as "kind of a goofy guy", one who concedes only to "giving the appearance of being busy", looks at serious risk of being undermined by high-profile success.

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We meet on a bright and cold Monday afternoon in a photographer's studio in Manhattan with spectacular views of the Hudson River. "Pretty great, huh?" says Mr Sudeikis, taking, somewhat dorkily, pictures of the view with his phone as we sit down by the window. He has just finished his shoot for MR PORTER a whole hour and a half early, unheard of when it comes to fashion shoots.

"Oh yeah, I was determined to win that prize and be the fastest fashion model ever," he says dryly. (He later admits that trying on clothes is "not my favourite part of the job", and seeing as he makes that confession while shrugging on an anorak and a battered rucksack, his profession to fashion ignorance does not seem like part of his easy-going self-deprecation but rather God's honest truth.)

Mr Sudeikis has a laconic, relaxed manner, talking slow and walking slow, that doubtless comes from his being a Midwesterner rather than a New Yorker, having grown up in Kansas. But mentally, he says, he has always had the kind of jittery and hyperactive curiosity that is a better reflection of his fast-moving career than his laid-back demeanour.

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"I didn't really want to be an actor when I was growing up - I wanted to be whatever I was reading about or seeing at the time. When I read The Firm I wanted to be a lawyer; when I saw Top Gun, I wanted to be a fighter pilot. So that's why acting probably turned out to be a good thing for me because I get to be people for five minutes or 90 minutes. I'd be curious to see if I had the attention span to be like those guys on 30 Rock and play the same character season after season," he says, as if unable even to imagine having a non-acting job that lasted for life as opposed to several seasons.

"Although there were two careers that did really interest me as a kid," he continues. "I wanted to be a basketball player, and when I realised that wasn't a real thing I wanted to be Axel Foley [Mr Eddie Murphy's character in Beverly Hills Cop]." So you were a white kid in Kansas who wanted to be black, I say. "Absolutely. And I see nothing unrealistic about that." Mr Sudeikis' ultimate decision to reject being Axel Foley in favour of being an actor was based, some might say, on equally unrealistic expectations, but ones that bore out. Mr Sudeikis' uncle is Mr George Wendt, aka Norm from Cheers, who was also a graduate of The Second City.

"Having George as an uncle made acting seem like a viable career. He met his wife at Second City so I looked at him and thought, wow, this Second City place, you go there, you marry a beautiful woman and you get a job on Cheers - that place sounds magical!" And that is near enough what happened to Mr Sudeikis, as he did meet his wife (now ex-wife), TV writer and producer Ms Kay Cannon, there and moved seamlessly to Saturday Night Live.

Mr Sudeikis has been frequently linked to various actresses by the celebrity press, from Ms January Jones to Ms Jennifer Aniston to one Olsen sister or another. He is currently dating Ms Olivia Wilde but the interest in his romantic life is one part of the job that makes him even more uncomfortable than trying on clothes. "Yeah, I don't really..." he begins, lost for words for the first time in an hour. "Uh, it is a little odd being chased around [by the press]. Fortunately all of the stories have been very flattering to me but it is weird to read stories that are completely untrue and you think, 'Where did this come from? Who is this source?' Like, there was a story that Jennifer Aniston and I were dating. Obviously she's dealt with it for years so she's as cool as a cucumber about the whole thing but I'm like, 'How did they even come up with that?' It's weird, and it would be easy to let it make you close up as a person, but you have to choose not to be that way." He pauses for a second. "You know, I think those magazines should hire me because I think I'd be really good at writing those articles. I'm pretty intuitive and good at making insinuations."

And just like that, a new career plan is born.

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