Guy Carter (Jason Biggs), an out-of-work architect desperate for money before his wife, Anne (Jenny Mollen), gives birth to their first child, replies to a Craigslist job ad for “drivers” thinking he’ll be delivering pizzas. But when he shows up to the gig, he’s informed by his employer, Zoley (Cedric Yarbrough), that he’ll be driving around prostitutes. Yoley, though, isn’t a pimp, only a dispatcher, because “Pimps got killed by Craigslist!” Arranging gigs from the counter of a burger joint, he works for Nikki (Janet Montgomery), a high-end prostitute, not the other way around. Guy takes the job, and quickly finds that he, too, works at the pleasure of Nikki, who expects him not only to drive, but to host shows, collect money, clean up, and provide protection as well (though Nikki seems more than capable of handling the last of these on her own).
Amateur Night, written and directed by husband-and-wife team Lisa Addario and Joe Syracuse and based on Syracuse’s experiences working for an escort service, is peppered with insights into the business of sex work (professionals, we learn, know how to get the most money for the least effort), but these are largely drowned out by a series of comic humiliations visited upon Guy, the apex of which sees him washing a bagful of dildos. The filmmakers want viewers to know this moment actually occurred; this is, after all, a film that not only features an opening title proclaiming “Based on a True Story (Mostly),” but an end-credits montage of all the scenes here that ostensibly really happened. But when such a scene is set to “Mr. Big Stuff” and played by Biggs with the same wide-eyed, I-can’t-believe-I’m-doing-this expression he used in the American Pie movies, it doesn’t exactly ring true.
In translating this inherently funny mostly-true-life material into a film, Addario and Syracuse have transformed it into the kind of broad comedy one expects to find Kevin Hart mugging his way through. The filmmakers compress Syracuse’s experiences into a loosely plotted one-crazy-night story, overloading it with extraneous wackiness like a car chase and a subplot involving a kinky doctor (Steven Weber). Amateur Night is constantly straining for laughs, mostly at Guy’s expense, but Addario and Syracuse have little sense of comic timing and no eye for framing their images in a funny way. The film acts as if the mere idea of watching Biggs crawl around on the floor picking up crumpled ones were hilarious in itself, but scenes like this more often comes off as desperate attempts to squeeze some big laughs out of a story that doesn’t really need this sort of artificial enhancement.
This is unfortunate, as Amateur Night contains glimpses of a more nuanced, earthbound work that could have been. In contrast to most popular depictions of sex work, the film portrays the industry as an entrepreneurial, woman-centered business, one with its share of dangers (robbery, handsy guys), but also plenty of benefits (the money, self-management). But while Amateur Night is peppered with interesting true-life details, these are overwhelmed by frantic comedic sequences. Ultimately, Addario and Syracuse are less interested in making a film about sex work than in offering the opportunity to see their lead actor get sprayed in the face with female ejaculate.