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The few movies in which the late River Phoenix starred were largely at best great and at worst decent at harnessing his wise-beyond-his-years soulfulness. A Night in the Life of Jimmy Reardon, written and directed by William Richert, is an outlier, an empty-air teen comedy that silos Phoenix into a role that requires he be a shallow womanizer whose motivating plight is sympathetic only to a point.

He plays the title character, recently graduated from high school and stuck in a kind of purgatory. His parents will only pay for his college if he attends his dad’s same stuffy business-school alma mater. If he refuses to, his parents are adamant he get a full-time job that can ensure he can pay for his share of the rent. Jimmy isn’t against college — he just doesn’t want to go to the one in which he’s being pressured to enroll. Not with enough money to his name to go his own way — he squanders the 100-something dollars he had saved at the beginning of the film after getting swindled by a one-night stand — he works listlessly as a photographer’s assistant in the meantime.

Then, he comes up with an idea. What if he were to sweeten up his going-nowhere life by eloping in Hawaii with his wealthy girlfriend, Lisa (Meredith Salenger)? She’s OK with an idea that seems based more than anything on Jimmy wanting to at last bed a girl who’s resolutely chaste; most of the movie will be spent seeing him trying to scrape together the measly $80 for a plane ticket to an island that, at the moment, is so paradisical-sounding that it might as well be Eden.

The film’s comic hijinks mostly arrive with a trail of empty air behind them; no one in the movie’s cast seems very comfortable with the arch bent of Richert’s stylized dialogue. I don’t require movie characters to be likable, but Jimmy, whose internal monologue is presented throughout the film through a noirish voiceover, also isn’t written substantively enough to render him compellingly complex as he treats all the women in his orbit thoughtlessly. (Lisa, though vexingly temperamental herself, is the subject of some nerve-racking physical aggression by Jimmy late in the film, a product of her being reasonably resistant to him after he blows off a make-or-break moment in their relationship.) Jimmy can still spark our empathy, though: we feel bad about the unfair bind in which his parents have put him, and Richert does a decent job portraying the appearance-keeping insecurities of a lower-middle-class character who has the bad fortune of having almost only obscenely rich friends.

Much of what I’m saying could, or could not be, reactions to things Richert had always intended or the rejiggerings the film’s studio had supposedly subjected it to after Richert presented what he had put together. A Night in the Life of Jimmy Reardon was based on a book Richert had written as a 19-year-old a couple decades earlier, Aren’t You Even Gonna Kiss Me Goodbye?, and his adaptation was ostensibly so interfered with by studio executives that he was moved to, decades later, release a director’s cut that’s been said to improve on the purportedly mangled product more widely accessible. Someday I might get around to it, but not before returning to the movies that much better harnessed the sui-generis sensitivity that made the prematurely departed actor at its center feel so much like a great gone far too soon.