Catherine Keener, right, and Sarah Steele portray a mother and daughter in Nicole Holofcener's darkly comic new film, Please Give. (Piotr Redlinksi/Sony Pictures Classics)

Wes Anderson shares his penchant for emotionally stunted characters. Todd Solondz approximates his misanthropy. And Noah Baumbach inhabits the same privileged, intellectual Upper East Side milieu. But when it comes to channelling Woody Allen in his heyday, Nicole Holofcener comes closest.

Writer-director Nicole Holofcener. (Matt Carr/Getty Images)

With her ear for naturalistic dialogue and keen understanding of human neuroses, Holofcener has been establishing herself as Allen’s heir(ess) apparent since her directorial debut in 1996. Riffing on Annie Hall’s theories about the horrible and the miserable, she has created a gallery of needy, acid-tongued characters, many of them embodied by her acerbic onscreen alter ego, actress Catherine Keener, who has appeared in every one of her films.

This is a world where women behave badly — it’s not uncommon in a Holofcener film to see her characters dropping f-bombs, stalking their exes or having meltdowns in store checkout lines. But scratch their high-strung, brittle exteriors, and you’ll find lonely, insecure humans underneath — people struggling with friendships, romance, body-image problems and enough guilt and inertia for years of therapy.

Many of these foibles are milked for awkward comedy, but Holofcener also has the ability to offer serious philosophical inquiries alongside the humour. Taking a cue from such triumphant Allen films as Manhattan (1980) and Crimes & Misdemeanors (1989), Holofcener’s often self-absorbed characters do turn outward to ponder questions about luck, charity, morals and mortality. As one sourpuss notes in Friends with Money, “Sometimes, you do the wrong thing … but while you’re doing it, you’re thinking, 'This doesn’t hurt anybody – what difference does it make?' Well, it does make a difference, because those little things add up.”

Holofcener explores these rich themes to great effect in her comic yet poignant new film, Please Give. Before it hits theatres April 30, we offer a tour of her previous gems, and look at the anxious, communication-challenged characters searching for meaning in her (godless) universe.

Walking and Talking (1996)

Premise: The lifelong friendship between Laura (Anne Heche) and Amelia (Catherine Keener) shows signs of strain when Laura gets engaged.

Themes: The give and take of female friendship; fear of change; the perils of losing your independence in modern romance.

Keener’s state of mind: Lonely, needy, obsessive and in denial about the impending death of her cat, Big Jeans.

Allen-esque moment: One of Laura’s therapy patients admits he’s been concocting stories about seeing little red devils for fear his own problems are too boring.

Best line: “My best friend’s getting married. That’s probably what’s making me sick.”

Lovely & Amazing (2001)

Premise: Three sisters (played by Emily Mortimer, Raven Goodwin and Keener) are forced to confront their own insecurities and body-image issues when their mother (Brenda Blethyn) undergoes liposuction surgery.

Themes: Fraught family relationships; issues of race and class; fear of aging; the importance of feeling comfortable in your own skin

Keener’s state of mind: Angry, immature, attention-seeking and in denial about the problems in her marriage.

Allen-esque moment: Elizabeth (Mortimer), an insecure actress, asks a lover to critique every inch of her naked body.

Best line: “I never eat. Ever. In fact, I'm dead.”

Friends with Money (2006)

Premise: Three privileged women (Joan Cusack, Frances McDormand and Keener) look on with pity and concern as their longtime friend Olivia (Jennifer Aniston) becomes a pot-smoking maid.

Themes: Female friendships; class; white liberal guilt; fear of aging; the notion that real charity comes with no strings attached

Keener’s state of mind: Accident-prone, neglected and in denial about the effect her third-storey addition is having on her neighbours

Allen-esque moment: Depressed designer Jane (McDormand) has a meltdown when people butt in front of her in the Old Navy checkout line.

Best line: “Is this too dressy for homeless people?”

Please Give (2010)

Premise: Bourgeois marrieds (Oliver Platt and Keener) sell overpriced vintage furniture pilfered from grieving families, and attempt to improve their prickly relationship with the women in the apartment next door.

Themes: Strained family bonds; white liberal guilt; body image; fear of aging; and the notion that real charity comes with no strings attached.

Keener’s state of mind: Privileged, worried, guilty and in denial about her ability to perform charity work without crying.

Allen-esque moment: Mistaking a black man outside a posh eatery as a homeless person, Kate (Keener) attempts to offer him her leftovers. Turns out he’s actually in line to get into the restaurant.

Best line: “Your feet hurt because you’re old, grandma. Things get worse, not better.”

Please Give opens May 7.

Lee Ferguson writes about the arts for CBC News.