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That Night Chases the One That Got Away in Chicago

Image courtesy of Broken Bulb Productions

When it comes to the “one wild night” concept, there are a pair of measurables that define the lengths the chosen movie aims to go. They center on the crowd and the setting. First, how many people become caught up in this evening adventure?  Second, are the characters in question tearing through an entire city with escalating or life-altering shenanigans or are things more isolated and intimate. Chicago-based filmmaker Zachary Trussell deftly plays with those two sliding scales to keep That Night quite interesting.

On Saturday, April 30th, Broken Bulb Productions hosted a night of entertainment for That Night’s premiere and Chicago’s passionate indie filmmaking community that made this kind of movie possible. It was hosted by the Logan Theatre. Proceeds from the event went to SkyART, an art therapy program that makes a positive impact on Chicago’s South and West Side youth and empowers them to express themselves and discover their potential through art. That was an outstanding cause as the film now enters the festival circuit.

That Night follows a budding artist named Stacey (Straight Edge Kegger’s Julio Montenegro) who would love to have his art career take off while bidding time working at a suburban tuxedo and tailoring shop. His sh*t-talking best friend Joey (Oscar Mansky of If You’re Gone) catches him early in the day to psych him up and to get transportation all set up. Stacey waffles as he entertains this night of partying with friends because there’s a good chance he’s going to run into his ex-girlfriend Lily (newcomer Julie Gester).

A gathering of people sit and stand in a bar.
Image courtesy of Broken Bulb Productions

It doesn’t take much “her and you breaking up was the best thing” opposing encouragement from Joey to see that Stacey still madly pines for Lily, no matter what answer he feigns. Lily may be with a questionable new guy and he himself has an eager work hookup in the form of the blond and fetching Carolina (Emily Sue Bengston of The Christmas Listing), but she’s the one that got away. Filling his head more than the incoming drinks, Stacey sees tonight as a chance to get back on her radar and turn her head.

The initial homebase for That Night is Schmidt’s (Michael C. Hyatt of Saturday Night Inside Out) house. He’s the grown up one of the bunch ready to propose marriage to his long-time girlfriend Andrea (Kendall McCarthy). Lily is Andrea’s cousin, and it’s from these intersecting circles of male and female friends that everyone knows each other (and their much-chided-about shared histories) as they walk through the door and come together before heading to the big city.

In true “one wild night” fashion, it’s a miniature odyssey just to get to Schmidt’s. He’s asked Luke (Terrence “Boogie” Williams) to pick up the engagement ring and ride with Joey and Stacey. Within the first fourteen minutes of That Night before the title card arrives at 10:30pm in-movie time, things already start to get weird and hairy for our traveling trio. Party prep can be as eventful as the eventual big soiree. Before the night is over, mixed up pills, a lost dog, mistaken identities, and an upstanding artist maven (Veronica Carr) get involved.

A surprised man is forceably removed from a bar.
Image courtesy of Broken Bulb Productions

The bar scene obstacle course for That Night starts at Sluggers in Wrigleyville. Care-free game is being spit and the spirit of one’s twenties are being enjoyed. And then Lily walks in. For Stacey, as well as all of us, the vibe, music, and speed of it all changes. The first greeting brings out equal attempts at flirting and stonewalling. The big question that grows from there is how can a night like this end.

Trussell, helming his first feature-length film after five short films, made plans for that and they reveal themselves with both gentle and not-so-gentle ribbing, where idiot friends never go away and big dreams appear to be seized, all in a matter of hours. That’s the aforementioned sliding scale where a whole city is the background to a very select group of people. The mostly diegetic music turns the party on and off for each scene change. The sidebar moments of action, reaction, and distraction captured by cinematographer Melissa Pratt and edited by Kevin Seeman have their zaniness and easy amusement.

A man and woman talk about art in a studio.
Image courtesy of Broken Bulb Productions

The trouble with being hung up on exes is the cha-cha-like dance steps forward and backward when it comes to either personal regression or personal progress. Wishing for old and better times might be a healing situation to correct a flawed present. Getting back together could also be an unrealistic wish for matters that cannot or shouldn’t be fixed. Has mutual self-improvement occurred to bring the two closer to being able to stay together or has time changed them for the better apart from what didn’t work? If there’s a big, overdue expression of commitment, can it be believed or reciprocated?

That Night may buzz around the living spaces and late-night haunts of the Windy City on a path to sunrises, but every pitfall or bit of good luck comes back to our main leads with karma and consequence. Through the boozy haze, Stacey and Lily confronting their uncertain futures is the locked core of the movie. Montenegro and Gester demonstrate excellent chemistry in their shared conversations where will-they/won’t-they cliches are challenged every step of the way. The balance of unhinged fun and important personal destinies are well-blended in That Night and more than hold audience attention. Find your own bar crawl or join theirs! You’re sure to have a good time.

Written by Don Shanahan

DON SHANAHAN is a Chicago-based Rotten Tomatoes-approved film critic writing here on Film Obsessive as the Editor-in-Chief and Content Supervisor for the film department. He also writes for his own website, Every Movie Has a Lesson. Don is one of the hosts of the Cinephile Hissy Fit Podcast on the Ruminations Radio Network and sponsored by Film Obsessive. As a school teacher by day, Don writes his movie reviews with life lessons in mind, from the serious to the farcical. He is a proud director and one of the founders of the Chicago Indie Critics and a voting member of the nationally-recognized Critics Choice Association, Online Film Critics Society, North American Film Critics Association, International Film Society Critics Association, Internet Film Critics Society, Online Film and TV Association, and the Celebrity Movie Awards.

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