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When the young men in the film Diner find a woman attractive, their preferred slang is to call her, “Death.” This is a specific tweak of the phrase, “she’ll be the death of me”: to these immature dude-bros, all in the early twenties, a woman represents an end to their identity, which is both frightening and somewhat inevitable. Released in 1982 and set in 1959, Barry Levinson’s seminal film Diner has not aged well, except for the novelty of seeing middle-aged actors like Mickey Rourke and Kevin Bacon in their prime. The new musical adaptation of the film, written by Levinson with songs by Sheryl Crow, adds halfhearted self-awareness to the drama but not much introspection. The performers and songs pop with retro energy, yet they cannot save the material from its retrograde battle of the sexes.

The biggest change from the film to the musical, aside from the obvious, is the addition of an omniscient narrator. John Schiappa plays an older version of Boogie, one of a handful of dudes who would regularly hold court in an all-night Baltimore diner. Over greasy sandwiches and endless coffee refills, they discuss the usual: music, gambling, the Colts, and sex. The loose plot revolves around Eddie (Adam Kantor), who plans to marry Elyse (Tess Soltau) in a few days. But before they tie the knot, Elyse must pass a detailed multiple-choice test about football, one that Eddie wrote for her.

The football test is immature and stupid, this is true, yet all the guys create similarly irresponsible problems for themselves. Shrevie (Josh Grisetti) is upset that he cannot talk to his wife Beth (Erika Henningsen), so he yells at her about his record collection. Fenwick (Matthew James Thomas) is a self-loathing alcoholic. Then there’s the younger Boogie (Dereka Klena), a would-be wise guy and ladies’ man who makes outlandish bets in order to get out of debt. Over the course of several days, leading up to the wedding and the end of the fifties, these guys sort of realize that youthful folly is no longer that cool.

Given the time period and Crow’s pop sensibilities, the songs are a mix of R&B, rock, and doo-wop, except tweaked slightly so they also have a cleaner Broadway sound. While the ensemble numbers are fun, with energetic choreography and surprising costume changes, the best songs are the smaller-scale ones. This is probably because one character signing (or two) will arrive at some sort of minor emotional epiphany, and because Sheryl Crow’s best songs sound like they’re for one specific person (“If It Makes You Happy” still holds up, give it another listen). Shrevie and Eddie share a song called “It’s Good,” where they croon about the modest appeal of marriage with a mix of warmth and scorn. An independently-minded woman named Barbara (Whitney Bashnor) signs “Don’t” when the man in her life tries to assert that he knows what’s better for her than she does (he doesn’t). Still, the most entertaining songs involve Fenwick since self-destruction is hilarious in the context of a musical, and Thomas has a soulful, involving voice. “Last Man Standing,” the last song of Act One that’s sung by Fenwick and the ensemble performers, is a show-stopper with a conceit that’s cheerfully sacrilege.

If Diner was just a revue of Crow’s attempt at a nostalgic musical, it’d be a smashing success. Unfortunately, Levinson’s handling of this material is a misfire; his clumsy attempt to update the plot is an implied insult, as if the addition a narrator makes up for Diner’s rampant sexism. The most infamous scene involves Boogie, where he tries to impress the guys and win some money with the old “penis in a popcorn box” trick. Director Kathleen Marshall puts the scene in a movie theater – given the lyrical content of the accompanying song, it’s a meta-update of Grease’s “Summer Nights” – except Levinson ignores the scene is about sexual assault, and peers who goad it. Older Boogie tries to explain away the immaturity, yet Marshall and the cast still prefer broad comedy, as if “boys will be boys” is explanation enough. If Diner did not include the Boogie’s commentary, it might work as sleazy camp (the actors certainly have enough chops for that). Instead, a meager “aw-shucks” admonishment of the scene exposes an ugly tolerance for disturbing behavior.

With excellent production values, including a set that regularly moves and rotates to accommodate the youthful cast, Diner sometimes move at an entertaining clip. Still, some songs are better than others, so it’s easy to question Levinson’s themes in the moments where the music starts to slag. Given its time period and subject matter, I kept comparing Diner to Mad Men, which is about archetypes from the same period (more or less). Mad Men also has nostalgia for the period, yet its criticisms have a harsher sting since Matthew Weiner, unlike Barry Levinson, does not let youth cloud his judgment. Most men remember how invincible and cool they felt in their prime. Diner is about that, too, except it lacks the wisdom that’s supposed to arrive when regret – about immaturity and women, more specifically – inevitably replaces youthful confidence.

Diner is at The Signature Theater until January 25. Buy tickets here!