Given Woody Allen’s cancelled, pariah-like status in Hollywood, it will probably do no favors to Jesse Eisenberg for me to compare his new film A Real Pain to Allen’s best work, but I’m going to anyway. A serio-comic film of genuine depth, nuance, and humanity that asks hard questions in a meaningful way, A Real Pain brings to mind the kind of films that Allen made with astonishing regularity in the 1970s and ’80s—Annie Hall (1977), Manhattan (1979), Hannah and Her Sisters (1986), Crimes and Misdemeanors (1989). Like Allen in his heyday, Eisenberg has proved himself to be an impressive hyphenate in writing, directing, and playing one of the lead roles, which, like Allen, trades heavily on a well-established screen persona defined primary by humorous insecurity. There is no demarcating where one role ends and the other begins, which is what makes Eisenberg’s work so seamless.

Not having seen his first feature directorial effort, When You Finish Saving the World (2022), I was unsure what to expect from Eisenberg as a filmmaker, and A Real Pain shows him to be one of uncommon maturity and confidence, which is most clearly evident in his lack of pretension and showiness. A Real Pain plays with a seemingly effortless grace and wise sense of pacing and humor; at no point does it feel like Eisenberg is trying to “prove something” as a director. Rather, he places a great deal of confidence in the weight of his story and how it is inflected by the odd-couple chemistry of him and Kieran Culkin as mid-30s Jewish-American cousins who are taking an organized weeklong trip through Poland in honor of their recently deceased grandmother, who was born there and managed to escape the Holocaust.

Eisenberg’s David is all Type-A tension and concern, his job in online marketing and his role as a husband and father marking him as distinctly different from Culkin’s Benji, who has a comfortable aura of slacker-can-doism that ultimately masks a deeper sadness and insecurity. In this way, they are flip sides of the same coin, with David wearing his insecurity openly on his sleeve while Benji hides it with extroversion and coy self-centeredness. The film suggests that they grew up together and were essentially best friends as kids, but have since grown apart as their adult lives have taken them in different directions, which is what makes the Poland trip such a sublime evocation of family history: In retracing their grandmother’s steps through Holocaust-ravaged Poland, they must face their own strained sense of sibling-friendship and test the strength of what is left.

Eisenberg structures that film’s plot around the tour, which gives it both a sense of organization and a shaggy-dog openness that allows for detours, drawn-out moments, and unexpected developments. The tour is led by a British Holocaust scholar named James (Will Sharpe) who, while well-meaning and affable, is ultimately revealed (but forgiven for) his inherent distance from the Jewish experience. The rest of the group is made up of an amusing assortment of types, including Jennifer Grey’s middle-aged divorcee and Kurt Egyiawan’s Eloge, a Rwandan genocide survivor who has recently converted to Judaism. Eisenberg has some definite thoughts about what it means to be Jewish and what it means to be American in a fractious world, and he allows much of it to come out through various conversations in which characters elaborate on their own identities, some of which are assured and others of which are tentative and confused. This extends, of course, to David and Benji’s relationship, as the latter is always pushing the former into places outside of his comfort zone. Benji also plays the role of disrupter, speaking the quiet part out loud, as it were, such as when he loses it emotionally over riding in first class on a train when 80 years ago he would have been in a cattle car. Much of the power of Culkin’s rightfully admired performance lies in his character’s ambiguity—whether he is genuinely invested in his outbursts or just playing a role; it is also driven heavily by a deep sadness that Culkin conveys beautifully and tragically.

That, of course, does not make A Real Pain sound very funny, but it is in a true and moving way. Eisenberg and Culkin play off each marvelously, and as a director Eisenberg proves particularly adept at mining the comedy of embarrassment while also setting it up to reveal deeper, darker truths. The film’s title cleverly plays it multiple ways, alluding to Benji’s difficult nature, but also to the horrors of the past and how the tourist-adventure of walking through it with a well-versed guide can only take you so deep; as Eisenberg has said in interviews, there is no “good way” to experience this past because it is always within the context of privilege. The pain is real, but the film’s beauty is in how it constantly reminds us of how it can be overcome.

Copyright © 2025 James Kendrick

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