The Skeleton Twins lost me in its opening moments. Lead characters Milo (Bill Hader) and Maggie (Kristen Wiig), on opposite sides of the country, contemplate suicide on the same day, with news of Milo's botched attempt to cut his wrists interrupting Maggie's contemplation of a pill overdose. It's a frustratingly neat bit of plot shorthand of which practically the whole film is guilty.
Milo and Maggie are twins who were close as children but haven't spoken in ten years, and they grew up marked by the suicide of their father at a young age; now reuniting in their upstate New York hometown, they're both trying to figure out what went wrong in their lives. Or something.
Writer/director Craig Johnson (this is his second film, after 2009's little-seen True Adolescents) lets our protagonists' backstory unfold out slowly over a gloomy, sardonic 90 minutes. Milo is a gay washed-up actor in LA who attempts to rekindle an affair with his closeted former high school teacher (Ty Burrell); Maggie is a hygienist who has hidden her mounting depression behind a relentlessly cheerful nice-guy husband (Luke Wilson) to whom she has trouble staying faithful. It seems implausible that the twins would have kept out of each other's lives for so long, but there's allusion to vague drama in the past (which eventually gets a little more fleshed out) and Milo has a manic edge that underscores the decision he made to flee across the country.
Hader and Wiig, unsurprisingly, have great chemistry together, the kind you can only forge by doing years of comedy together in a high-pressure network TV environment (probably). Hader is the standout of the pair, giving the more extroverted Milo much more pathos than exists on the page and deftly steering away from all the predictable stereotypes of the acid-tongued gay guy in his mid-30s. Wiig is once again handed a very dry, gloomy character to try and flesh out — I worry that her tendency towards deadpan humor in early movie roles like Knocked Up and Extract has locked her into this rather dull type. Maggie is trying to convince Milo, and herself, that she's happy in her safe, harmless marriage, but the writing is on the wall from about minute one.