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5 Films That Exemplify Nicole Holofcener’s Radical, Character-Driven Brand of Filmmaking

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The filmmaker behind “Friends with Money” and “Enough Said” has devoted her career to creating multidimensional lead characters. That continues with her latest, "The Land of Steady Habits."

Prickly, disgruntled, bitingly witty — these aren’t traits you typically find in female film characters, who are most often written to be sympathetic and inviting. Yet this is exactly the type of character that Nicole Holofcener, the writer-director behind favorites like “Friends with Money” and “Enough Said,” has devoted her career to creating. Generally off-putting yet still strangely alluring, Holofcener’s characters are real and multidimensional, the type of person prone to lying and stealing and lashing out. But even when the rest of these characters’ worlds are crumbling around them, they often cling to their friendships with fierce loyalty and love.

Holofcener’s newest, “The Land of Steady Habits,” now available on Netflix, finds her turning her perceptive lens for the first time ever onto a male character: a divorced ex-banker named Anders Hill (Ben Mendelsohn). Like many of her previous protagonists, Anders is irritable and aimless, having recently quit his job in finance and left his wife and son to live out his middle age on his own. But when he shows up at his ex-wife’s friend’s dinner party one night and strikes up an odd friendship with the couple’s troubled teenage son Charlie, things start to get messy.

Following a long career of depicting female friendship, “The Land of Steady Habits” finds Holofcener foregrounding the complexity and power of male relationships: between Anders and his son, Anders and Charlie, and even Anders and his wife’s new boyfriend. But unlike other male-driven stories, Holofcener’s take benefits from a discerning female perspective, and she also manages to carve out ample screen time for the bond between Anders’ ex Helene (Edie Falco) and her best friend Sophie (Elizabeth Marvel). With a unique female gaze and her familiar brand of deadpan wit and spunk, the movie represents both a fresh new direction for Holofcener and an excellent addition to her expanding body of work.

With the release of “The Land of Steady Habits” on Netflix, we’ve assembled five of Holofcener’s best films below to get you up to speed on her unique cinematic voice.

“Walking and Talking” (1996)

Holofcener’s beloved writing and directing debut “Walking and Talking” set the stage for a long career of droll, female-driven work to follow. The movie centers around childhood best friends Amelia (Catherine Keener) and Laura (Anne Heche), whose closeness is threatened when Laura gets engaged to her longtime boyfriend. Left lonely and listless, Amelia’s only solace is the video store she rents from every night, but things get complicated when she decides to go out with the store’s nerdy, schlubby video clerk. The female friendship comedy was a perfect launchpad for Holofcener, commencing a years-long collaboration with Keener (who was nominated for an Independent Spirit Award) and cementing Holofcener as a bold and clever female voice to follow.

“Lovely and Amazing” (2001)

Five years later, Holofcener returned with “Lovely and Amazing,” another story of female relationships — this time among a mother (Jane Marks), her two grown-up daughters Michelle (Catherine Keener) and Elizabeth (Emily Mortimer), and an adopted 8-year-old named Annie (Raven Goodwin). The women are bright and charismatic, but dysfunction stems from societal pressures, such as Elizabeth’s insecurity about her looks, and relationships with men, like Michelle’s resentful husband whom she accuses of stomping on her art sculpture. The result is a discerning comic take on modern womanhood, exposing the real trials faced by mothers and daughters at all stages of life.

“Friends with Money” (2006)

A few other familiar faces joined the mix in “Friends with Money,” which stars Jennifer Aniston as Olivia, a single, disaffected, marijuana-smoking maid whose group of longtime best friends (Joan Cusack, Frances McDormand, and Keener) are all comfortably married. Each of the friends has their own private problems — McDormand plays a grouchy nut, Keener quarrels with her husband as they cowrite screenplays — but Olivia seems to be the one who’s got it worst, floundering with money problems as she searches for a suitable boyfriend. Like a less polished, more true-to-life version of “Bridesmaids,” the ensemble comedy might not be Holofcener’s best-known work, but the bittersweet story is notable for its bold subversion of female tropes and its sublimely realistic take on female solidarity.

“Please Give” (2010)

This dark comedy, which won the Robert Altman Award at the Indie Spirits, finds Keener on stabler ground: she plays a furniture dealer with a guilty conscience who lives with her husband (Oliver Platt) and teen daughter, who are all waiting for the elderly woman next door (Ann Guilbert) to pass away so they can absorb her apartment into theirs. Some of the film’s best acerbic humor derives from interactions with the old woman’s granddaughters, who represent two ends of a spectrum: Rebecca (Rebecca Hall) is attentive and loving, while Mary (Amanda Peet) is a crabby alcoholic. Once again, Holofcener assembles a band of real, difficult women — as irritating as they are irresistibly relatable.

“Enough Said” (2013)

Holofcener’s most popular film to date, “Enough Said” follows Julia Louis-Dreyfus as a divorced masseuse named Eva who double-crosses her new boyfriend (James Gandolfini, in one of his final roles) by befriending his ex-wife (Keener, of course) and milking her for relationship dirt. Sharply written and genuinely hilarious, the movie is also more upbeat than some of Holofcener’s other, more deadpan comedies. But that’s not to say that she sugarcoats this one — Eva is just as real and alive as the rest, striving to make her new relationship work despite the less-than-appealing info she gleans from his ex. Beloved by fans and critics alike, the movie is a worthy last hit before Gandolofini’s untimely death (he received a posthumous Screen Actors Guild Award nomination), as well as a delightful addition to Holofcener’s oeuvre, leaving everyone excited for whatever would come next.

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