20 Films and Series That Highlight the Reality of the Generation Gap

In just ten episodes (so far), Jean Smart and Hannah Einbinder have established themselves as an iconic duo. Smart plays Deborah Vance, a legendary yet outdated stand-up comedian who is forced to confront her fading relevance as her audience ages. Einbinder portrays a disgraced comedy writer hired to revitalize Vance's act. While primarily a comedy, the series delves into the complexities of its characters, avoiding superficial bonding moments in favor of exploring the nuanced dynamics between two vastly different individuals.

Where to stream: HBO Max

Only Murders in the Building highlights how, in the 2020s, true crime podcasts have become a unifying force across generations. Steve Martin and Martin Short, two men of similar age but contrasting personalities, join forces with Selena Gomez, a millennial, after discovering their shared obsession with a specific true crime podcast. This shared interest propels them to investigate a murder in their upscale New York apartment building—a residence only Martin's character can truly afford. Despite their differences, the series delights in showcasing how Gomez and her older counterparts navigate their generational and cultural divides to collaborate effectively.

Where to stream: Hulu

This miniseries is undeniably unique, and its eccentricity may not appeal to everyone. However, at its core, it’s a story about forging connections. The narrative brings together three generations: Jason Segal and Andre Benjamin, two men grappling with midlife identity crises; Eve Lindley, a young trans woman seeking to break free from isolation; and Sally Field, a woman in her 70s who has spent her life caring for others and now seeks to rediscover herself. The series emphasizes the value of learning from one another’s perspectives, despite their differences.

Where to stream: Fubo, AMC+

Few can claim a parent-child dynamic as uniquely captivating as that of Carrie Fisher and Debbie Reynolds. While not universally relatable, their relationship is undeniably intriguing. Fisher penned the screenplay, adapting it from her semi-autobiographical novel, with Meryl Streep and Shirley MacLaine portraying characters inspired by the real-life duo. Directed by the legendary Mike Nichols, Postcards is a star-studded production that underscores how familial bonds can endure even the most profound hardships.

Where to stream: Fubo, Showtime Anytime

Holiday gatherings often amplify generational tensions, as seen in this 2021 indie film directed by Stephen Karam, adapted from his Tony-winning and Pulitzer-nominated play. The story revolves around three generations of a family—featuring standout performances by Beanie Feldstein, Richard Jenkins, June Squibb, and Amy Schumer—who come together in a dilapidated New York City apartment for Thanksgiving. The cramped space quickly exposes buried conflicts, sparking debates over topics like sexual politics, religion, family duties, and even popular TV shows. As the apartment begins to feel like a trap, viewers might find themselves grateful their own family gatherings aren’t quite as chaotic—or reconsider their holiday plans altogether.

Where to stream: Fubo, Showtime, DirecTV, digital rental

In this Denzel Washington-directed adaptation of August Wilson’s play, fences serve as both physical and metaphorical barriers. Central to the story is the strained relationship between Washington’s character, Troy, and his son Cory, portrayed by Jovan Adepo. Cory aspires to football stardom, while Troy, haunted by his own unfulfilled dreams, tries to shield his son from similar disappointment. Though Troy’s concerns are grounded in practicality, his approach is tainted by fear and resentment, creating a rift that only he fails to recognize.

Where to stream: Digital rental

Surprisingly thoughtful for a raunchy comedy, Neighbors delves into the unsettling realization of aging. Seth Rogen and Rose Byrne portray new parents struggling to adapt when a rowdy fraternity moves in next door. Their attempts to assert authority or prove they’re still cool backfire hilariously, escalating into an all-out neighborhood feud. While the film doesn’t offer a clear moral, it suggests that embracing maturity might be the key to reconciling with the past—or the frat next door.

Where to stream: Digital rental

Shot over 12 years, Richard Linklater’s cinematic triumph (one of many) chronicles the evolving relationship between Ethan Hawke’s Mason Evans Sr. and Ellar Coltrane’s Mason Evans Jr. The film captures the family’s journey through separation, reconciliation, and transformation, portraying the complexities of parenthood and childhood with striking authenticity. If there’s a lesson here, it’s that parent-child dynamics are inherently challenging, and the only way forward is to navigate the difficulties head-on.

Where to stream: The Criterion Channel

While some may laugh, this film resonates deeply with those who’ve grown up in devoutly religious households, especially with queer children in the mix. The dynamic between Carrie (Sissy Spacek) and her mother Margaret (Piper Laurie) feels eerily familiar, minus the telekinesis and climactic bloodshed. Carrie doesn’t offer much hope for reconciling stark generational divides, but it serves as a stark reminder to avoid burdening our children with our own unresolved issues.

Where to stream: Digital rental

While rooted in its time, this story remains universally relatable. A $10,000 life insurance payout sparks tension within a multi-generational family. Ruby Dee’s Ruth and her son Walter Lee (Sidney Poitier) clash over how to use the money: she prioritizes stability through homeownership, while he dreams of opening a liquor store for future financial security. Their debate reflects broader generational divides, pitting conservative values against youthful ambition, all against the backdrop of Civil Rights-era struggles.

Where to stream: The Criterion Channel

Jean Smart continues to shine, this time as a starkly different character from her role in Hacks. In this series, she portrays the sharp-tongued, no-nonsense mother of Kate Winslet’s Detective Mare Sheehan, who is investigating a murder in their small town. Smart’s character is a force to be reckoned with—brash, opinionated, and often harsh, yet fiercely devoted to her family, serving as Mare’s unyielding support system.

Where to stream: HBO Max

While packed with humor, this Netflix animated film centers on the strained relationship between aspiring filmmaker Kate Mitchell and her tech-resistant father, Rick. Their initial family conflict escalates into a global crisis when rogue AI threatens humanity. In an attempt to mend their bond, the family embarks on a road trip to take Kate to college—a questionable plan at best. However, as the world teeters on the edge of chaos, the Mitchells must unite, with Rick and Kate finding common ground to ensure their survival.

Where to stream: Netflix

Tracy Turnblad (Ricki Lake), a high school student in 1962 Baltimore, dreams of dancing on the Corny Collins Show. Her mother, Edna (Divine), initially disapproves, believing it’s unbecoming for a respectable young woman. However, after witnessing the prejudice of other local mothers, Edna realizes that times are changing and that there’s no harm in letting loose. Sometimes, bridging the generational gap simply requires parents to relax and embrace new perspectives.

Where to stream: Digital rental

The generational tension in this story is amplified by Jack Nicholson’s Schmidt, a character with few redeeming qualities. He’s not malicious, but he’s unremarkable—lacking curiosity or skills beyond basic survival. As he confronts his mortality and the emptiness of his life, he finds himself powerless to change. His only significant action is disrupting his daughter’s (Hope Davis) wedding, disapproving of her choice of partner. Yet, his most profound realization is that he has no right to dictate her life—a lesson many parents could benefit from.

Where to stream: Hoopla

Satyajit Ray’s Apu Trilogy chronicles the life of its protagonist from his birth in a rural Indian village to his adulthood in urban Calcutta. Central to the narrative is the complex relationship between Apu and his mother Durga, who has grown emotionally distant due to life’s hardships. While they never fully reconcile their differing perspectives, their dynamic offers a starkly realistic portrayal of parent-child relationships. Ray’s work transcends its cultural and temporal setting, highlighting universal themes of love, regret, and guilt that resonate across generations.

Where to stream: HBO Max, The Criterion Channel, Kanopy, Plex

Yasujiro Ozu’s quietly heartbreaking masterpiece follows elderly parents visiting their children and grandchildren. While there’s no overt conflict, the younger generation views them as a burden, eventually sending them to a spa to avoid inconvenience. The film poignantly underscores the fleeting nature of time and the regret that comes with neglecting familial bonds. It serves as a powerful reminder of the importance of cherishing moments with loved ones before it’s too late.

Where to stream: HBO Max, The Criterion Channel, Kanopy

In this film, the roles are reversed: it’s the parent who inspires the child. Christopher Plummer portrays Hal Fields, a man who embraces his true self by coming out as gay in his 80s, much to the surprise of his son Oliver (Ewan McGregor). As they navigate this new chapter, Oliver undergoes significant personal growth, inspired by his father’s courage and newfound happiness in living authentically.

Where to stream: IMDb TV

This series explores a unique generational dynamic, with a roughly twenty-year age gap between its protagonists. Set in 1950s Cambridgeshire, Robson Green plays Geordie Keating, a weary WWII veteran and detective, while James Norton (and later Tom Brittney) portray idealistic local priests who assist in solving murders. Despite their friendship, tensions arise as Geordie’s hard-earned cynicism clashes with the younger men’s optimism, reflecting a timeless generational divide—though one that feels less pronounced in today’s world, where even the young have faced significant challenges.

Where to stream: Prime Video, PBS Passport

Decades before Ozu’s Tokyo Story, Leo McCarey’s Make Way for Tomorrow portrays the struggles of an elderly couple who lose their home to foreclosure. With no job prospects or Social Security (this was 1937), they turn to their children for support. Like Tokyo Story, the film avoids casting villains, but the children find caring for their parents burdensome, eventually separating them into different households and considering nursing homes. The film was a poignant call for improved elder care in America—a message that remains relevant today.

Where to stream: The Criterion Channel

James Dean perfectly captures the essence of teenage turmoil—confusion, shame, and inner conflict. It’s a shame his parents couldn’t grasp what he was going through.

Where to stream: HBO Max