This episode confirmed my suspicion: Chuck is on a roll. The jokes are punchier; Chuck's taking a more active role in the spy stuff; Morgan's not nearly as annoying. And while guest stars were not very successful last season (I expected more from you, Rachel Bilson), tonight saw not one, but two near-perfect outside castings.
Both factored heavily into the story, which was a riff on the 1982 comedy My Favorite Year. The first was silver fox John Larroquette in the role of Roan Montgomery, a rogue agent so well trained in the art of seduction, he makes even stone-faced Diane lose her composure. (Side note: When the camera first found him, I thought for a second that the show had scored Tim Robbins.) He's tasked with taking Chuck as his disciple when it's revealed that the real cipher is in the hands of the Black Widow, a woman who takes men to bed, then kills them. Chuck's sent in because she'd never suspect he's an agent, and he can flash on objects in her hotel room that may lead the team to the cipher's location. Thus begins a series of fumblings while Chuck adjusts to the person Roan is forcing him to be–Roan barks "This isn't happy hour at Chili's!" while Casey, who flunked out of Roan's class back in the day, listens in, perhaps to learn a thing or two himself.
But the process exposes something that's been discussed for a while: Chuck's fake relationship with Sarah is finally starting to take its toll. It's getting to the point where his family is noticing how real Chuck perceives the fake relationship to be–Ellie points out that when he looks at Sarah, it always seems like he's doing so for the first time. It doesn't help things that Chuck unfortunately had his shot blown in the last episode, and that successfully completing this mission will get him even closer to having another. The stakes create a ripe set-up: he must convincingly seduce another woman to finally awkwardly seduce the woman of his dreams.
Of course, the Black Widow still stands in his way, played deftly by Melinda Clarke–another welcome guest star. Any fan of Josh Schwartz's The O.C. knows her Julie Cooper always had an ulterior motive–and the actress did a great job of keeping her cards close to her chest. The same work is on display here: Chuck goes through the whole song-and-dance, jumping on his own lines before winning her over with his cock-of-the-walk monologue. (Nice recovery, though, from the evening's first snafu-slash–funny point from Roan: How can you seduce someone without alcohol?) But turns out the Black Widow has been conning him all along; she knows Roan's tactics when she sees/hears them, and realizes Chuck is, in fact, a spy.