I'm not sure if writer-director Nicole Holofcener titled Friends with Money to purposely name-check the Jennifer Aniston sitcom, but her new film—starring Aniston is essentially sitcomedic. Just perhaps, if those TV Friends settled into upper-classy domestic lives, they might trade their stressed-out joie de vivre for the depressive ennui of Holofcener's women and men.
Happily, Holofcener gathers four endearing leading ladies: Aniston, Frances McDormand, Joan Cusack, and Catherine Keener. As the only single woman in her gaggle of friends, Aniston's Olivia is the only one who has to worry about money. Naturally, the characters' money doesn't necessarily spackle over personal troubles. Keener plays a TV writer married to her writing partner (Jason Isaac); both partnerships flounder as they contribute to suburban blight by building a tower on their home. McDormand's Jane—married to a self-deluding gay man (Simon McBurney)—has serious anger issues and a depression that's sapping her will to live. The richest couple, Cusack's Frannie and hubby Matt (Greg Germann), lives in domestic bliss troubled only by occasional guilt issues over their affluence.
Writer-director Holofcener gives the characters relatable failings and the story some ironic bite. When Matt invites the skeptical gang to an ALS benefit dinner, he insists, "It'll be fun!" (thereafter, everyone promptly forgets what the benefit's for...homelessness perhaps?). The friends give each other support, but also gossip about each other relentlessly, and Holofcener paints their lives as series of disappointments with only a few glimmers of happiness.
Ultimately, Friends with Money lacks the depth of empathy Holofcener showed in Lovely and Amazing—the writer can't entirely decide whether she wants to redeem her characters or viciously satirize them (and who wants wishy-washy satire?). And the characters' failings can feel contrived, as when Olivia, who works as a maid, submits to the humiliations of a jerky boyfriend (Scott Caan). Still, there's a fair amount of truth in the troubled, tunnel-vision worldview of these friends with money.