Olivia (Jennifer Aniston) is a pot smoking, sort of employed maid suffering from extreme depression. She's surrounded, judged, and supported by her long time group of friends (Joan Cusack, Frances McDormand, and Catherine Keener), who are all living wealthy, successful lives in Los Angeles. Feeling overwhelmed by her past mistakes, Olivia finds herself at rock bottom, only to see that the people she believed had everything they want are just as emotionally battered as she is.
Writer/director Nicole Holofcener is an incisive observer of female relationships, and "Friends with Money" furthers the strong filmography she's building that also includes the pointed, first-rate films "Walking and Talking" and "Lovely & Amazing."
Holofcener is able to expose the uncomfortable truths in life, and in "Money" she focuses on the growing pains of being 40 years old – the magic number society has deemed as the finish line for people to get their act together. However, Olivia is not written as a pathetic individual, lazily watching life and her friends pass her by; Holofcener has made certain to convey that the character is simply in neutral, due to many factors including romantic disasters and her own disappointments in life. Olivia is a rounded, nuanced character who desires the happiness that she long ago forgot how to achieve.
Jennifer Aniston gives the role a nice, restrained reading, helping the filmmaker get across the idea that Olivia is not a trainwreck, which would be much easier to both write and act. Aniston delicately inhabits the make-up-sample-hoarding, perpetually wounded character with poise, and the actress's innate sugary humanity gives the role life. Aniston succeeds at refusing to play Olivia in an overtly sympathetic way, but she still remains unnervingly relatable.
The friends with money, however, have the more flamboyant roles. "Money" is a robust character piece, allowing the supporting talent to really go for broke with their performances. Holofcener's script is tight and funny, but it gives the actors time to explore their numerous quirks. Franny (Cusack) is the passive-aggressive friend with a bloodless marriage and a need to judge, Christine (Keener) is the guilt-drenched friend with a crumbling marriage, and Jane (McDormand) is the friend with a personality disorder, married to a man who amusingly takes metrosexuality to the brink of flat-out homosexuality. Under Holofcener's assured direction, the three supporting players are fantastic, but McDormand is the one who holds the screen. Unable to recognize that her mental stability is slowly leaking away, McDormand gives a full-throated performance as Franny, alternating uncomfortably between hilarity and horror as she furiously deals with the rude drivers and disrespectful waiters that disrupt the course of her day.
Much like her previous work, Holofcener has some trouble tying together a finale for her movie. The picture goes off in so many directions that finding a single concluding scene becomes pointless. Holofcener simply goes for moments of hope in the film's closing moments, and she achieves it with sharply written dialog, and four wonderful actresses who give "Friends with Money" a frightening dramatic authenticity that Holofcener is so skilled at achieving.