1. Young Adult (2011)
Charlize Theron plays Mavis Gary, a ghostwriter for a young adult series who returns to her hometown to wreck her high school sweetheart's marriage. Mavis is the queen of unlikable protagonists; she's delusional, selfish, and unapologetically flawed.
Her bitter, sarcastic humor and spectacular failure to grow up feel like a character Cummings would write, embodying a dark refusal to accept adulthood gracefully. The film's cringe-inducing honesty and sharp dialogue make it a perfect tonal match.
2. Sleeping with Other People (2015)
This film stars Jason Sudeikis and Alison Brie as two serial cheaters who form a platonic friendship to cure their toxic relationship habits. The movie is packed with the kind of rapid-fire, witty banter about sex, fidelity, and emotional baggage that defines Cummings' stand-up. It bypasses easy rom-com tropes for a smarter, funnier, and more realistic look at why modern relationships are so complicated.
3. Obvious Child (2014)
Jenny Slate plays a stand-up comedian who gets dumped, fired, and pregnant just in time for Valentine's Day. The film's blend of raunchy humor and genuine vulnerability is pure Cummings. It tackles a serious topic with an unflinching, comedic lens, refusing to moralize or simplify the protagonist’s messy, complicated decisions. It's a story about a woman navigating a crisis with the only tools she has: jokes and brutal honesty.
4. Shiva Baby (2020)
This film is a 77-minute panic attack. A young bisexual woman's life implodes when she runs into both her sugar daddy and her ex-girlfriend at a Jewish funeral service with her parents. The sheer, claustrophobic cringe of the situation, combined with the protagonist's terrible decision-making, creates a symphony of social anxiety. It’s a masterclass in uncomfortable humor and captures the feeling of being trapped by your own lies, a theme Cummings frequently explores.
5. Bachelorette (2012)
Often unfairly dismissed as a 'Bridesmaids' knock-off, this dark comedy is far more acidic and chaotic. Three deeply dysfunctional friends (Kirsten Dunst, Lizzy Caplan, and Isla Fisher) nearly ruin their friend's wedding with a night of cocaine-fueled mayhem. The characters are cruel, narcissistic, and hilarious in their self-destruction, reflecting the darker, more cynical side of female friendship that Cummings often mines for comedy.
6. The Worst Person in the World (2021)
While a Norwegian drama, this film's portrait of a young woman named Julie navigating her love life and career with chronic indecision feels universal. It perfectly captures the millennial anxiety of feeling like you're running out of time while also not knowing what you want. Julie's restlessness and her tendency to blow up her life in search of the next thing will feel deeply familiar to anyone who appreciates Cummings' commentary on relationship ambivalence and personal chaos.
7. Appropriate Behavior (2014)
Desiree Akhavan writes, directs, and stars in this film about a Persian-American bisexual woman in Brooklyn trying to win back her ex-girlfriend while struggling to come out to her family. The humor is dry, the protagonist is messy and specific, and it nails the feeling of cultural and romantic disorientation. Its blend of sharp wit and raw, personal storytelling makes it a spiritual cousin to Cummings' work.
8. Plus One (2019)
Two longtime single friends agree to be each other's dates for a summer packed with weddings. The dialogue is fast, funny, and feels incredibly real, focusing on the gallows humor required to survive wedding season in your late 20s. It’s a rom-com that’s more comedy than romance, with a cynical but ultimately hopeful core that aligns with Cummings’ knack for finding the hilarious pain in modern rituals.
9. The To Do List (2013)
Aubrey Plaza stars as a nerdy, overachieving valedictorian who creates a sexual to-do list to complete before she goes to college. The film flips the script on the typical male-led teen sex comedy, approaching its raunchy subject matter with a kind of clinical, awkward hilarity. It’s a funny, female-centric take on sexual discovery that’s less about romance and more about clumsy, awkward experience—a classic Cummings-esque theme.
10. Enough Said (2013)
This film offers a more mature but no less neurotic vibe. Julia Louis-Dreyfus plays a woman who starts dating a great new man (James Gandolfini), only to discover he’s the dreaded ex-husband of her new friend. The resulting anxiety, secrets, and awkwardness are handled with incredible comedic timing and emotional honesty. It explores the insecurities of dating after divorce with a warmth and wit that feels both sophisticated and deeply relatable.
