Review: Lost Holiday Loses Track of Its Own Characters, Mystery

Starring a collection of some of the more interesting names in indie filmmaking and directed by the Matthews Brothers (Michael Kerry and Thomas, who also co-stars in the film), Lost Holiday is a whimsical but not especially substantial character study of 20-something college friends who reunite in their old stomping grounds in and around Washington, D.C., and get caught up in an unexpected mystery that they are determined to solve, more out of boredom than any real investment in the outcome.

Friends Margaret (Kate Lyn Sheil) and Henry (Thomas Matthews) travel do D.C. from their current home in New York, and meet up with Margaret’s old boyfriend Mark (William Jackson Harper, from Midsommar and “The Good Place”), who is now engaged and living a frustratingly domesticated life, as are many of their old friends. As if to prove they still cling to some thread of their reckless youth, Margaret and Henry go to bar after bar, drinking themselves blind and eventually end up in the house of a drug dealer named The Russian (Tone Tank), searching for acid with their friend Sam (Keith Poulson).

Lost Holiday Image courtesy of Visit Films

At some point in the evening Margaret witnesses what she thinks is an attempted kidnapping, and when reports surface that a singer and heiress named Amber Jones (Ismenia Mendes) has gone missing, Margaret becomes determined to piece together her whereabouts. The plot of Lost Holiday sounds more serious than anything in the actual film. Margaret and Henry are a bit unbearable at times and not generally people you feel like spending time with or even observing as a casual audience member. They take nothing about life seriously, and every useful accomplishment comes to them almost accidentally. Their amateur sleuthing does garner results, but through a humorously back-door route. Sheil does at least make the thought of being around a character like this somewhat tolerable, but it’s a long, uphill battle. Margaret is struggling to find her place in the world as an adult, and we get a sense that this adventure might be her saying goodbye to her wild years, while Henry just feels stuck.

Lost Holiday certainly captures the exuberance and selfishness of being young and irresponsible. I just wish anything about the film’s mystery storyline felt like any consequences were at stake. There are a couple of quick appearances by such greats as Joshua Leonard as a shady record executive and Isiah Whitlock Jr. as a detective investigating the kidnapping, as well as the silky voice of Emily Mortimer as an NPR announcer we hear throughout the movie. It’s a film with small ambitions, and that’s exactly what we get as a result.

The film opens today for a weeklong run at Facets Cinémathèque.
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Steve Prokopy

Steve Prokopy is chief film critic for the Chicago-based arts outlet Third Coast Review. For nearly 20 years, he was the Chicago editor for Ain’t It Cool News, where he contributed film reviews and filmmaker/actor interviews under the name “Capone.” Currently, he’s a frequent contributor at /Film ( and Backstory Magazine. He is also the public relations director for Chicago's independently owned Music Box Theatre, and holds the position of Vice President for the Chicago Film Critics Association. In addition, he is a programmer for the Chicago Critics Film Festival, which has been one of the city's most anticipated festivals since 2013.