Directed by Nicole Holofcener

Sony Pictures Classics

4 stars

Last week, I said to my roommate, only slightly drunk and only half kidding, that if I didn’t find a husband while I’m in Greece this summer, I would probably never get married or be financially secure. After seeing “Friends with Money,” my worries are gone: I never want to get married or make money—apparently, such a lifestyle only leads to intense psychosis, homophobia, greasy hair, and really prominent wrinkles.

Nicole Holofcener’s painfully sad and wickedly smart new film is a study of middle age: “Friends with Money” focuses on four women as they enter, with trepidation, tantrums, and biting wit, into middle-age, but moreover it highlights how four actresses who were conventionally charming and cute in their thirties—Jennifer Aniston, Catherine Keener (“Capote”), Frances McDormand (“Almost Famous”), and Joan Cusack (“School of Rock”)—have matured into four phenomenal acting forces.

The frighteningly gaunt Cusack plays to perfection the uptight, consistently critical (and annoyingly right) friend you (or at least I) love to hate. Some of the sharpest lines of dialogue are delivered by her nasally Chicagoan voice.

Keener, who might have been doomed to always play parts similar to her role in “The 40-Year-Old Virgin,” here delivers an extraordinarily nuanced and tear-jerking performance. Christine is married to David, the definition of a completely insensitive jerk—made easier to believe as the actor, Jason Isaacs, plays Lucius Malfoy in the “Harry Potter” series. The moment when she silently realizes that she is better without him—conveyed simply by her dynamic facial expression and a well-framed shot of her husband’s empty chair—packs more feminist punch than “The First Wives’ Club” or “The Divine Secrets of the Ya-Ya Sisterhood” combined.

McDormand ups the neurotic ante of her performance in “Almost Famous,” but as her character spirals into insanity, Holofcener’s dialogue can’t keep up the pace. Her on-screen outbursts are the most forced demonstrations of emotion in this very bittersweet movie; fortunately, her subtle displays of affection with her (speculated to be gay) husband, Aaron (Simon Burke) sweeten every scene they play together.

The film really centers on Aniston’s character, Olivia, and her attempt to get her life back in order. Aniston, as a pothead who is hung up on her last boyfriend, lacks motivation, and steals wrinkle-reducing cream, is simultaneously hilarious, tragic, and completely relatable. This side of the former “Friend” is better even than the quirky losers she played in “Office Space” and “The Good Girl.”

In its triumph of the single woman, the importance of long-lasting friendship and frank discussion of class conflict, Holofcener’s film borrows heavily from feminist playwright Wendy Wasserstein, especially the material of “The Heidi Chronicles,” “Uncommon Women,” and “Old Money.” The portrayal of the perplexing nature of female depression in “Friends with Money” seems to echo Michael Cunningham’s book and 2002 screenplay “The Hours.” At the same time, this movie strives for the sexual humor and heart-warming friendship of “Sex and the City”—unsurprising in that Holofcener directed several episodes of the seminal show.

Despite these influences, “Friends with Money” transcends becoming a clichéd dystopian narrative or chick flick, in part because of its pensive cinematography and a mournful, unique Rickee Lee Jones soundtrack. The film really captivates, though, because of its freshness as a distinctly post-feminist, post-boomer, twenty-first century story. It frightened me so much that these familiar feeling women—who have broken the glass ceiling, had their perfect children, built their Barbie dream home, and still have amazing social lives and fabulous shoes—are supposed to be the role models to whom I look up, but even they are dissatisfied and depressed upon turning 43. Where the fuck are we supposed to go from here?

Surprisingly, it was Aniston [full disclosure: I loathed Rachel] who really wins the most sympathy and raises the most questions for me. Maybe because of the fact that in the aftermath of Brangelina, Aniston’s been portrayed by everyone from US Weekly to Katie Couric as a “victim,” she seems heartachingly human on-screen. If someone that well-coiffed and perfectly sculpted—and by this I mean both the actress and the character—dates idiots, doesn’t know what to do with her life, and has body image issues, then I guess everyone can feel a little better about their own slumps and failures.

Bottom Line: Don’t expect to leave the theatre uplifted about life or hopeful about finding Mr. Right—at least until your forties. But even the greatest cynic will be moved by “Friends with Money’s” outstanding acting and its resolution that the best things in life are supportive friends and that special someone to tell you you’re the prettiest person in the room.

—Staff writer Kristina M. Moore can be reached at moore2@fas.harvard.edu.