Why Can't Louis Be Happy?

When Louis C.K. brought Louie to FX four years ago, his lovable-loser gags were agonizingly believable. He seethed with misery and self-loathing, whether his masturbation jokes were about doing it to the wedding album he discovered in the garbage or doing it while the Twin Towers were falling down. But it's a different joke four years later, now that he's turned his anti-social brilliance into a groundbreaking TV success, turning into a world-beating comedy legend in the process. By now he's the loser slob as warrior king.

5 Things We Learned From the Season Premiere of 'Louie'

So why does he still despise himself so much? That's the question that makes Louie darker than ever as the fourth season begins. After all, Louis C.K. is the guy we can all dream of being. He's the everyschlub's best-case scenario. He's at the top of the food chain, even if every link in the chain is a Cinnabon. And he's too smart to pretend he doesn't know it – but instead of making him cocky, it seems success has beaten him down. In the new season, every joke seems to ask, "If I'm such a genius at being a loser, why am I still such a loser? And how late is that Cinnabon open?"

It's definitely the most negative and claustrophobic season of this never-exactly-bubbly sitcom. Each week, we see the misadventures of the struggling comedian and divorced dad, fumbling through awkward dates and soul-crushing gigs in sleazy clubs. And he's feeling his age, even though it's tough to imagine this guy was ever young. "Life is short – a lot of people are fond of saying that," he says in one of the stand-up bits. "And it is. Life is short – if you're a child who died. But at 46, it's not short anymore. It's long, man. Life – it feels like it's taking a long time to get through this shit."

Believe the man. His world has grown tinier. His social life is more dismal, if you can imagine that. Last season looks like a party by comparison. It took real creative ambition for Louis C.K. to strip his psyche down to even more depressing basics, but he was willing.

Louie finds total humiliation wherever he goes, even when Jerry Seinfeld is personally recruiting him for a charity benefit gig. ("Can you work clean?" Seinfeld asks him. "Can you not say 'dirty sex poop dogs having sex with vagina dirt'?") He bombs in front of audiences and even more so when he tries asking women out. After a surprisingly successful sexual experience, he explains to the woman he's in bed with, "It isn't how I roll." He's right – it isn't.

See Louis C.K.'s 10 Funniest Moments

In a way, the main reason he keeps the stand-up comedy segments is they're the closest he comes to a sincere human connection, if only in the ritualized moments where he tells the audience, "Thanks a lot, you guys – you've been very nice." He doesn't mean it, and they know it, but there's an honesty in the showbiz artifice. The audience is the most uncomplicated and rewarding relationship in his life – a bunch of strangers he can talk to and then leave behind. He reveals much more of himself to them than he does to any of his friends – even when he makes confessions like, "You know you love somebody when you share your innermost secret racism with them."

Louis C.K. is bigger than ever, yet in his moment of triumph he's retreated to the darkest, loneliest corners of his life because that's where he feels at home. It's a bold move – with all the reasons you might admire this guy, envy him, fantasize about being him for a day, he'd still rather make you worry about him. And when it comes to cranking up the worry factor, nobody can touch him.

This story is from the May 22nd, 2014 issue of Rolling Stone.