Following a chance encounter at a comedy club, the 60-something Best invites his 29-year-old ex-employee to spend Memorial Day weekend with him at his Connecticut country house. Curious about a man she has worshiped since childhood, she accepts. “I’m going for fun,” June tells her roommate. “Did I tell you he has a pool?”
Despite the comedic premise, comedic personae and Seussian rhythm to “June Bloom,” don’t expect a rollicking weekend: In Connecticut, there’s a pool, but almost no fun. Despite their late-night pedigrees, Best and Bloom don’t riff. They don’t heighten each other’s jokes or do impressions. Instead, before they even uncork the weekend’s first bottle of wine, the two are grilling each other about the psychological catalysts for pursuing a career in comedy. “It’s not always something in their past,” Best tells Bloom about comedians, “sometimes it’s clinical. Is it clinical for you?” The idea that any comedian would non-ironically engage in a conversation about the clinical causes and underlying pathology of late-night jokes is, well, laughable.
And yet these protagonists are unable to laugh at themselves, or mine their tragedies for humor. Bloom volunteers that she’s had an abortion, then apologizes: “I’m not trying to be flip about it.” Why not? You’re a comedy writer! Be flip! Flip away! For his part, Best confesses that his father was “distant. Ragey. The type of person who would hit a kid with a closed fist.” His mother “had boundary issues of her own.” In terms of comedy-writer verisimilitude, the lack of flip is fatal.
Like Letterman, Best also weathered a sex scandal — one that, Bloom reflects, makes you wonder if “you could like the artist but not the man.” Unfortunately unlike Letterman, Best lacks the talent, charisma or creativity that might persuade you to try. (A classic Hugo Best zinger: “He’s tiny and his suits are tiny. If you looked at the size on the tag it just says T for tiny.”)
Not much happens. The weekend unfurls like a Greenwich lawn: a languorous expanse partitioned by various mansions. Bloom meets Best’s shock-jock neighbor and scowls at his jokes in his backyard; Bloom meets Best’s teenage son and scowls at his jokes in his backyard. In the car, Best puts on a Steve Martin record; Bloom asks if he ever listens to NPR. At a bar, she leaves a stand-up set to wander around a Walgreens. A Walgreens! The least amusing drugstore there is!