Unlike "Border," I found it hard to get into the show-within-a-show plot of "Little Italy." Basically, Benjamin is investigating a story about a treasure of New York's Little Italy that's in danger of being pushed out: Little Little Italy. Literally, it's a tiny Italy, with miniature people, miniature bicycles with miniature loaves of bread in the miniature baskets. Benjamin interviews the people about their history, falls in love with a miniature woman who gives him a miniature hand (or…blow?) job, and inadvertently sparks a turf war with the leader of the regular sized Little Italy mafia.
Then, when the war is over—Little Little Italy villagers getting stomped upon while Benjamin looks on from a doll-sized window, unable to help—Benjamin walks out and joins the rest of his crew. They've just been sitting there waiting, oblivious to the saga that unfolded before our eyes. Benjamin, shell-shocked, quietly drives away.
The whole "anti-climactic ending to an extremely climactic scene" sketch comedy trope is best used sparingly. It's purposely defeatist, and works best when the weirdness and stakes of everything preceding are both extremely high. A lot of that build, though, was lost in Jon Benjamin's dry sense of humor and (on occasion) flat delivery. On a scale of one to 10, he hovers around a four or five the entire sketch. Thus the ending feels unsatisfying, and it sucks a lot of the energy out of "Little Italy."
Of course, Benjamin is pretty low energy in every sketch, but it works when it's called for. In another great piece of gonzo footage (like last week's "You Can't Shoot Here!"), Benjamin hits the streets of Brooklyn to take people's pulse on the gay marriage issue. But he makes it extremely difficult for them to respond. He goes into a movie theater, waiting until the film starts before asking his question to the patrons. He stops an old man on the street, but takes a call during the interview. A New York bus driver refuses to speak to him because, of course, he's driving the bus. It's a joy to watch the reactions of people who, in the absolute least likely of situations, find themselves face-to-face with an incredibly direct, incredibly deadpan guy with a microphone.
Actually, now that I think about it, there really weren't that many sketches in "Little Italy." There's something at the beginning about a guy who was mangled in a horrible farm equipment accident, and Benjamin interviews the guy who originally interviewed the victim; then Benjamin tries to talk to the shredded-face guy, passes out, and later gives his own interview to the original interviewer. (Deep, man.) In another quick burst of a segment, Jon Benjamin instructs old people on the use of computers. The majority of "Little Italy" is devoted to the "Little Italy" bits. Benjamin was originally worried about the show feeling too monotonous, so he added the breakdown sketch elements, where one of the stories unfolds and gets Benjamin directly involved. But "Little Italy" has way too much Little Little Italy stuff (essentially a simple payoff for some wordplay) and not enough to temper it.
The show is still finding its footing, though, so I'm able to overlook the messier parts of the bit and enjoy the core concept of the show. Where else would the mobster genre be stretched so thin as to include a tiny (and it turns out, underage) woman pleasuring Jon Benjamin? Nowhere. Jon Benjamin Has A Van is a risky endeavor, playing on unsettling sketch tropes and the whims of a guy who has pretty far out comedic ideas. Much like any comedic world, the longer you spend in it, the more enjoyable it becomes, and "Little Italy" is a less effective detour down a strong sketch road.