Film Review: Indie Entanglement Is a Twisted Bit of Comfort Food

After a painful divorce, Ben (Thomas Middleditch from “Silicon Valley”) has decided he is inconsolable and attempts to kill himself. But each time he tries, something unexpected keeps him from going through with it. It’s not that he has no one in his life; he’s just reluctant to let anyone (including his parents) in for fear of having his heart crushed again.

entanglement film Image courtesy of the film

He attempts therapy with some degree of success, and his very caring neighbor Tabby (Diana Bang) can usually give him a reason to smile each day. But neither of these things stop him from feeling like somewhere along the line of his life, something went sideways that has kept him from feeling centered from day one.

Then he discovers the startling news that his parents once adopted a baby girl, but right when they got her home, they found out they were pregnant with Ben and were forced to give the baby back. Somehow this revelation that for one brief day he legally had a sister gives Ben a new purpose, and he sets out to find her. As it turns out, he’s already met the young woman at his local pharmacy.

Jess Weixler (Teeth) plays Hanna, an adventurous, spirited force that seems almost too good to be true, as she slowly draws Ben out of his funk by simply giving him a glimpse at an alternative version of his life growing up. Their relationship takes a turn for the weird as they find themselves attracted to each other, and before long Ben begins to realize that Hanna may not be all he believes her to be.

From a script by Jason Filiatrault, Entanglement is the second feature from director Jason James (That Burning Feeling), and it certainly dives into some dark corners of the human heart as it looks at love, connection and heartbreak with a more philosophical slant than most other films about romantic relationships. Some of its more major turns aren’t as unexpected as the filmmakers probably think they are, but Middleditch and especially Weixler are highly watchable, engaging actors who sell this warped story in ways other actors may not have.

I’ll admit to not being 100 percent sure what the underlying message of this film might be, but it’s a voyage of self discovery, hopefully toward something better in Ben’s life, and that’s what gives it a hopeful vibe that I liked. Not essential viewing, but if you’re looking for something off the beaten path that’s different than the rest, this is a twisted bit of comfort food.

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.