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When The Last Five Years premiered in 2001 in Chicago, Jason Robert Brown’s inventively structured musical about a break­-up was deemed to be so similar to real-life events that Brown’s ex­-wife threatened legal action. But the verisimilitude of the show’s depiction of love and heartbreak—in this case, between a successful author, Jamie, and a struggling actress, Cathy—is what made it such a cult favorite among musical theater fans. “Jamie is sure something wonderful died,” Cathy says in the show’s opening number, a mournful introduction to the end of a marriage. “Jamie decides it’s his right to decide. Jamie’s got secrets he doesn’t confide. And I’m still hurting.”

In the long­-awaited film adaptation, Anna Kendrick’s Cathy sings “Still Hurting” while sitting on the floor of a cold, gray apartment, her face hollow and deject. It’s an extraordinarily moving scene that seems to promise great things—namely that the vehicle of film might enable the kind of solid acting that musical theater often lacks the subtlety for. Kendrick, to her credit, is lovely as Cathy throughout, burnishing her reputation as the 21st century’s go-­to actress for musicals (see also: Pitch Perfect and Into the Woods), but the rest of The Last Five Years never quite makes the awkward transition from stage to screen. The plot, which in the musical juxtaposes present­-day Cathy with Jamie at the beginning of their relationship, and then follows his plot forward and hers backwards, is the kind of complicated gimmickry that works well on stage, where Cathy and Jamie meet only once, in the middle (their wedding day). But the director, Richard LaGravenese, understandably chooses to film the two together throughout, which makes for considerably more dynamic viewing, but also makes the chronology almost impossible to follow.

Things are hampered, too, by Jeremy Jordan’s Jamie, a character rendered so unlikeable it’s hard not to imagine Brown himself wanting to sue for having his stage avatar interpreted as such a consummate asshole. Jordan, a Broadway veteran, never seems to figure out how to tone down his performance for the much more intimate realm of film—in his first song, “Shiksa Goddess,” he crows and beats his chest and leaps up and down like a post-­college Peter Pan, turning his first sexual encounter with Cathy into a braggadocious account of his delight at finally hooking up with a Gentile. This early enthusiasm could be forgiven, but paired as it is with the years-­later scenes in which Jamie’s evolved into a better­dressed, more-­narcissistic version of the same arrogant bro, and with Kendrick’s impossibly charming and understated Cathy, it skews the audience’s sympathy in one direction from the get­-go.

The story, now almost 15 years old, manages not to feel too dated, as it traces Jamie’s speedy path from novice writer, to rising star (“The Atlantic Monthly’s printing my first chapter, two thousand bucks without rewriting one word,” he sings in “Moving Too Fast”), to literary darling. He’s billed as “the new Franzen” and promoted at a seemingly endless series of book parties. Cathy, by contrast, starts the movie as something of a failure, and then obviously continues in the same direction, chronicling her depressing summers doing musical theater in Ohio, and a series of unsuccessful auditions. The lower she gets, the higher Jamie flies, until the pair are bitterly fighting and trading resentful barbs toward the end of their marriage. “I will not fail so you can be comfortable, Cathy,” Jamie tells her. “I will not fail because you can’t win.” (Seriously, what a guy.)

The unbalanced nature of the adaptation makes for a basically unsatisfying experience (Jamie, a jerk, gets his way with everything, and Cathy, a sweetheart, doesn't), but there are moments of real delight in the movie, interspersed among some of the more clunkingly awful songs. Kendrick manages to dazzle in every scene she’s in, and though she doesn’t necessarily have the strongest voice in a handful of songs, the lack of Broadway polish seems to make for a more realistic performance. “A Summer in Ohio” cuts between scenes of her rehearsing with a handful of disinterested dancers, sharing a backstage dressing room with a stripper and her snake, and Skyping with Jamie about her litany of woes, making them seem funny all the while. And if Jamie has a redeeming moment, it’s oddly right after he wakes up in bed with a series of different women and wrestles with his guilty conscience in the song “Nobody Needs to Know.” “All right—the panic recedes,” Jordan sings. “All right—everybody bleeds. All right—I get what I need.” But something in Jordan’s face belies the blithe justifying going on, and makes the character seem a little more troubled in the face of his own betrayal.

In what’s essentially a spoiler-­embracing premise—the movie begins, and ends, with heartbreak, only on different sides—LaGravenese’s conclusion has a notable amount of poignancy to it and a real sense of sadness. Some stage productions of The Last Five Years have managed hopeful notes at the end, with Cathy singing her heart out at the excitement of new love, and Jamie, sadder and wiser, bidding her goodbye. This adaptation seems to choose bleakness instead, an ending that’s probably more honest, but that casts a heavy pall over things and only enhances the movie’s message that life isn’t fair. Apparently love isn’t, either.

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