Top 10 Movies Similar to A Real Pain You Should Watch

For fans of Jesse Eisenberg’s acclaimed dramedy A Real Pain, there are numerous other films that evoke similar themes and emotional depth. Blending Holocaust drama with buddy comedy, A Real Pain features Eisenberg alongside Kieran Culkin in a captivating story about two estranged cousins embarking on a poignant journey through Poland to honor their late grandmother. Eisenberg’s character, David, is the epitome of neurosis and self-doubt, while Culkin’s Benji brings a lighthearted, candid contrast.

The dynamic between David and Benji is both entertaining and touching, as the film beautifully explores their reconciliation. If you’ve enjoyed A Real Pain, which is currently available for streaming on Hulu, you’ll find a treasure trove of similarly themed films worth watching. This includes road-trip narratives featuring mismatched pairs, such as Sideways and Planes, Trains, and Automobiles, as well as character-driven stories addressing the lasting impacts of the Holocaust, like Harold and Maude.

10 When You Finish Saving the World

Julianne Moore in When You Finish Saving the World

Continuing the exploration of family dynamics, Eisenberg’s sophomore directorial effort, When You Finish Saving the World, mirrors the heartfelt journey of A Real Pain. This film, starring Julianne Moore and Finn Wolfhard, delves into the complexities of mother-son relationships as they navigate their emotional barriers; the mother supports domestic abuse survivors while the son pursues a music career.

Eisenberg’s knack for character-focused storytelling shines through in both films, highlighting nuanced relationships rather than intricate plots.When You Finish Saving the World serves as an impressive introduction to Eisenberg’s unique filmmaking voice, which has now garnered Oscar recognition.

9 The Darjeeling Limited

Owen Wilson, Adrien Brody, and Jason Schwartzman praying in The Darjeeling Limited

Wes Anderson’s The Darjeeling Limited presents a narrative parallel to A Real Pain. Both films feature characters on a quest of self-discovery, with The Darjeeling Limited following three brothers navigating their father’s death across India. While A Real Pain examines grief stemming from a grandmother’s passing, both stories oscillate between humor and poignant tragedy.

Critically reassessed over time, The Darjeeling Limited is now seen as one of Anderson’s more underrated works. The rich portrayal of sibling bonds resonates similarly to the cousinly connection in A Real Pain, and both directors exhibit an eye for capturing the landscapes central to their narratives.

8 His Three Daughters

Elizabeth Olsen, Carrie Coon, and Natasha Lyonne sitting on the couch in His Three Daughters

Another poignant family drama that gained acclaim in 2024 is Azazel Jacobs’ His Three Daughters. The film showcases three estranged sisters, played by Carrie Coon, Natasha Lyonne, and Elizabeth Olsen, who unite under challenging circumstances when their father falls ill. As tensions surface while sharing space, the authenticity of their familial bond shines through.

Much like the on-screen chemistry between Eisenberg and Culkin, the sisterly dynamics reveal common domestic struggles and resonate deeply with audiences, thanks to its dialogue-rich storytelling and understated visual style.

7 The Farewell

Awkwafina and The Farewell cast look at the camera.

The absence of Grandma Dory in A Real Pain serves as a powerful narrative force, mirroring the themes explored in Lulu Wang’s The Farewell. In this heartfelt tale, Awkwafina portrays a young woman confronting the impending loss of her beloved grandmother due to terminal illness. The family organizes a wedding as a cover for their final reunion, allowing them to bid farewell without revealing the truth to the matriarch.

Awkwafina’s dynamic with Zhao Shu-zhen exemplifies deep familial love, reflecting the far-reaching impact of loss that resonates strongly in both films.

6 The Squid And The Whale

Jesse Eisenberg as Walt Berkman speaking in a hallway in The Squid and the Whale

Jesse Eisenberg’s breakout role as Walt Berkman in Noah Baumbach’s semi-autobiographical film The Squid and the Whale captures the emotional fallout of parental divorce through the lens of two young boys. Eisenberg’s portrayal of teenage awkwardness resonates with audiences while addressing familial complexities and uncomfortable truths.

Baumbach’s influence is evident in Eisenberg’s directorial work, with both filmmakers adeptly highlighting raw, relatable emotions interlaced with humor.

5 Sideways

Paul Giamatti's Miles looks forlorn in Sideways

Similar to A Real Pain, Sideways encapsulates a journey of two friends addressing their personal struggles against the backdrop of a road trip. The film follows Miles and Jack, portrayed by Paul Giamatti and Thomas Haden Church, as they drive through California’s wine country for a bachelor party, confronting challenges such as marital woes and existential crises along the way.

Featuring a mix of humor and emotional depth, Sideways cleverly portrays male friendship while tackling heavier themes, mirroring the journey undertaken by David and Benji.

4 Harold And Maude

Harold and Maude in a field in Harold and Maude

Exploring contrasting perspectives on life, Harold and Maude mirrors the dynamics in A Real Pain, as it delves into themes of existentialism and mortality. Bud Cort stars as Harold, a young man fixated on death, while Ruth Gordon’s Maude, a spirited 79-year-old, inspires Harold to embrace life.

As a Holocaust survivor, Maude’s outlook on life deeply contrasts with Harold’s cynicism, ultimately illuminating the beauty of life amidst darkness.

3 The End Of The Tour

Jesse Eisenberg as David Lipsky looking at and talking to Jason Segel as David Foster WallaceThe End of the Tour

In The End of the Tour, Eisenberg plays Rolling Stone writer David Lipsky, who shares a deep connection with author David Foster Wallace (Jason Segel) during the latter’s book tour. The film emphasizes introspection and shared experiences, reflective of the emotional journey found in A Real Pain.

The underlying themes of loneliness and connection resonate throughout, showcasing the intricacies of human interaction.

2 Planes, Trains, And Automobiles

Steve Martin and John Candy sitting outside in Planes, Trains, and Automobiles

John Hughes’ classic Planes, Trains, and Automobiles presents a similar blend of comedy and drama featured in A Real Pain. The dynamic between uptight Neal Page (Steve Martin) and affable Del Griffith (John Candy) mirrors Dave and Benji’s relationship, presenting relatable challenges and growth throughout their unconventional journey.

Both films adeptly navigate humor while addressing deeper emotional currents, ultimately proving that even the most challenging experiences can foster meaningful connections.

1 Little Miss Sunshine

Little Miss Cast of Little Miss Sunshine in the van

At its core, A Real Pain embodies a bittersweet narrative, much like Little Miss Sunshine. This film follows a dysfunctional family as they embark on a road trip to support their daughter Olive at a beauty pageant. The ensemble cast—featuring standout performances—reflects the intertwining of love and disappointment inherent in familial relationships.

As the family navigates their own dreams and disappointments, the journey emphasizes resilience and connection, culminating in a poignant reflection on support and expectations.

Source & Images