This season of 'Boardwalk Empire' has been spiraling down a drain, and the further we go down, the more tightly coiled it becomes. "Devil You Know" posits the obvious question implied by the title, but it also darkly toys with ideas of judgment of character and role reversal, while delivering a tense episode and an emotional beating.

Tonight's title comes from its most emotional arc, that of Chalky White, perhaps the most doomed character of the entire series. Michael K. Williams has instilled Chalky with such depth and dimension over the course of five seasons, turning an unfaithful husband and career criminal into an empathetic character. The unsympathetic male protagonist has become a common fixture of the modern television landscape, thanks in part to guys like Walter White and Don Draper, but let's not forget their forbears on HBO's 'The Wire,' where Williams previously made Baltimore gangster Omar Little into one of the most empathetic and beloved characters -- even though he too was a thug and a murderer. But like Omar, Chalky lives by a code, a set of his own particular morals and ethics which allow us to identify with him, and like Omar, Chalky's very personal story over these five seasons has emotionally invested us, making his death incredibly difficult to watch.

The moment he cuts a deal with the slippery Narcisse, we know his death warrant has been signed. And "Devil You Know" imbues Chalky's final hour with so much tragedy, but it also allows him a graceful final bow, sacrificing his life for the hope of freedom for Daughter Maitland and her (and his, as it turns out) daughter. It still allows us a glimmer of false hope, even though, if you're anything like me, you were likely screaming at Chalky to take the bullets out of the gun before he handed it over to Narcisse -- as pointless as that would have been. In his final moment, Chalky tells Narcisse that it's all a dream, that "Ain't no one ever free," and with that, Chalky gets the last dignified word. In a world such as this, it's perhaps the only measure of justice and grace that a man like Chalky White could ever hope to be granted.

"This is where hope," as our drunken Nucky's new companion says, "comes to get f---ed in the asshole." Tonight's episode asserts that the devil you know is certainly no better than the devil you don't know, and Nucky learned that long ago. A bereaved Nucky takes a time out to get wasted in a bar full of people searching for their rock bottom, but even when he's pretending to be someone he's not, he can't escape his troubles. Just ask Eli and Van Alden how well this is working out for them in Chicago.

"Devil You Know" is one of the most bleak and pessimistic episodes of the entire series, and while there's something graceful about the end of Chalky White, there's absolutely nothing elegant about the end of Nelson Van Alden -- it's a total horror show. Whether criminal or agent, it's every man for himself, and Van Alden with his gloriously short fuse was dangerously close to blowing it. There is some poetic justice in Van Alden's end, given the cruelty he's inflicted on others, and although we've relished in Michael Shannon's fantastic performance over these five seasons, his death feels grotesquely right. Eli Thompson's punishment, on the other hand, seems far more harsh: a crumpled up wad of cash and the directive to buy a bus ticket, condemned to keep living his sad sack life, and likely unable to return to his wife. I wonder if Mrs. Van Alden needs a new "Huss-band."

The only real levity this week comes from the drunken women who rob Nucky, perhaps tired of womanizing schmucks like him taking advantage of them, and out to take a little agency for themselves. It's fitting, really, that someone like Nucky, given his history with women, would get beaten up and robbed by a couple of women from a bar after trying to hook up with both of them in an alleyway.

Drunk and passed out in the alley, Nucky is found by Joel, the kid Mickey hired to help with shipments. Confused and dreaming of his deputy days on the boardwalk, Nucky yells at Joel, calling him a thief, but it seems as though he's merely yelling at the younger version of himself. Past and present collide, as Joel echoes Nucky's past. "I'm trying to get ahead," he says, before refusing the cash Nucky offers because he doesn't want to live in a world where people help each other just to help themselves. It calls to mind little Nucky, returning the man's money from his hat when he was just trying to get ahead. Was he honest or just naive?

Additional Thoughts:

  • I am in serious mourning over the death of Chalky White. I probably have not made such cries of agony since watching 'The Wire.' ANGUISH.
  • "I am a kangaroo. How do you do? In my pouch I have a kazoo."
  • I didn't discuss it above, but the flashback reveal of little Gillian Darmody was heartbreaking and fit beautifully with the tone of this week's episode, especially given that we know who Nucky's about to introduce her to, and what that does to affect her entire life. For a second, I thought the kid was going to say his name was Jimmy, so, nicely done.
  • Speaking of 'The Wire,' when the hell does Prezbo come back? We've only seen Jim True-Frost's Eliot Ness once this season.