A dismal, D-grade sitcom stretched out to wafer-thin feature length, Shari Springer Berman and Robert Pulcini's Girl Most Likely sounds like it was written by somebody who has never heard a single real-world conversation. This is a film composed exclusively of simplistic potshots and walking clichés, its humor strictly confined to the lowest-common denominator in both content and execution. This is where wit and comic timing go to die; every joke is dated, shopworn, and tiresomely bland. It's difficult to imagine anybody involved with this project having real, honest conviction in the quality of the material (one hopes, at the very least, that this was just a paycheck for the otherwise enormously talented Kristen Wiig), and it's even more difficult to reconcile the film's tepid, warmed-over look and feel with Berman and Pulcini's still-great American Splendor, a film Girl Most Likely couldn't be less like. The couple's 2007 film, The Nanny Diaries, was clearly a big step in the direction of commercial homogonization and, if you'd like, of "selling out," but not even that suggested the duo could be capable of work this abysmal.
The story here is older than dirt, though the details are of course squeaky-clean: Failed playwright and lovably neurotic Imogene (Wiig, fighting a losing battle with this screenplay) fakes attempted suicide in order to win back her archetypically distant Wall Street boyfriend, and in doing so inadvertently convinces a doctor to place her in the emergency care of an immediate relative, who of course turns out to be the estranged mother (Annette Bening) she's been avoiding for years. Bening, who appears to not even be trying anymore, trucks Imogene's whining ass out of New York and back to nearby-but-backwater Ocean City, where she must deal with her mother's self-consciously oddball live-in boyfriend (Matt Dillon, happy to be working), the obvious Potential Romantic Partner Who Rents a Room in Their House (Darren Criss), and a schlubby brother who carries around a fiberglass bodysuit modeled after the shell of a mollusk (don't ask). Naturally, Imogene gradually learns to overcome her creative torpor and appreciate the people closest to her, and the film is literally without a single moment of surprise or unpredictability; as the endless forward march of bad jokes and hollow characters carries on, you can all but see the film ticking off the boxes on the generic rom-com checklist on which it was clearly based.
A frustrating end-credits cameo by none other than Whit Stillman provides a comparison so self-damning that it practically qualifies as auto-critique: Stillman's coming-of-age comedies—and, in particular, his two most recent works, The Last Days of Disco and Damsels in Distress—are inconspicuously radical feminist works of the highest order, and they tell the stories of young women finding their social and artistic voices in a sophisticated manner Girl Most Likely could never even hope to emulate. Forcing a comparison is more an ill-considered self-indictment than a humble homage. To paraphrase one of The Last Days of Disco's funniest one-liners, Girl Most Likely isn't fit to lick the boots of Stillman's four films.