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ENTANGLEMENT: review and interview with director/producer Jason James


Hi folks, Precious Roy, here, with a look at ENTANGLEMENT. It’s an existential Dram-Com of the indie variety, going to some fairly dark places along the way. It stars Thomas Middleditch (SILICON VALLEY), Jess Weixler (TEETH, THE GOOD WIFE), and Diana Bang (THE INTERVIEW, BATES MOTEL), was written by Jason Filiatrault, and directed by Jason James (THAT BURNING FEELING).
I got a lot out of ENTANGLEMENT; it’s a movie I hope you’ll see, because it does some clever things beautifully, and I think it’s a great experience to see it for the first time, unspoiled. There’s a meta level to this movie that was handled admirably by the writer, the cast, and their director.
I got a chance to talk to Jason James about this film… but our interview, unfortunately, spoils some really great things about ENTANGLEMENT. As such, the pre-interview part of this will be spoiler-free, but at the midway point, spoiler warnings must go up. I hope you’ll seek out the movie before reading the interview or my full review.

Above is the trailer that got me wanting to see this film, and I think it’s one of the better trailers I’ve seen in the past year, in terms of drawing an audience in without ruining the central fun of the film.  ENTANGLEMENT is about Ben (Middlemarch), a mentally-ill young man going through a soul-crushing divorce. In the opening scene, we are introduced to him as he awkwardly attempts to take his own life… first with a hosepipe, and then slashing his wrists in the bathtub. Ben survives but remains deeply depressed, trying to map out how his life went so terribly wrong with a Sharpie, some tape, red yarn, and a bare wall. It’s here where we meet two women in his life: the straight-laced neighbor girl Tabby (Bang), who helps Ben look after himself, and the very-impromptu Magic Pixie Dream Girl, Hanna (Weixler).
During his Dad’s awkward mild heart-attack crisis, Ben is presented with an important clue: he very nearly had a sister, once upon a time. Convinced that she may be the lost piece to his life puzzle, he goes to find her, and in a cosmic coincidence, discovers she’s Hanna. As Hanna and Ben bond, the fledgling neo-siblings fall in love with each other, as Ben’s mind continues to grasp for some measure of control over a past he is not really ready to let go of.
That’s all I want to give if you’re willing to go see the film. But there’s more, and that will come after this
The key achievement of ENTANGLEMENT is a brilliant takedown of the Manic Pixie Dream Girl trope. It casts out that simplistic fantasy of young, nymphet women created to be bon vivant guides for men to sort out their wounded souls out as puerile fantasy, and utter hogwash. It deals with fixation, and the idea of finding a path to just let go of your past, instead of miring your heart in lost opportunities and the disappointment of losing.
What’s really at the heart of ENTANGLEMENT is Ben’s struggle with his own mental illness, and his friendship/relationship with Tabby, the neighbor who saved his life. The keystone moment is Ben arriving home to find that Hanna has broken into his apartment. As he argues with Hanna about her break-in, Tabby knocks on the door. Ben hides an unwilling Hanna, just before Tabby opens the door with his spare key. As Tabby enters and asks a deceitful Ben about the girl he’s hiding from him in the bedroom, we see the heartache in a jealous Tabby as she opens up before him, seeing her chances with Ben slip away. It’s a very familiar scene, and yet completely fresh.
The crucial twist to the film is one I didn’t realize until shortly after this keystone moment: Hanna is, in fact, not real. Ben’s unreliable mind has invented a Manic Pixie Dream Girl to be a surrogate for his ex-wife and to ease his own loneliness.
There are a million clues to this… the fact that Hanna just happens to be the sister Ben was seeking… the delusions of magic and whimsy they share… Hanna’s strange dependence on Ben… Ben’s arguments with his reflection… their encounter with cartoon deer and jellyfish in a public pool… the man who chases Ben out of the swimming pool but fails to notice Hanna. It’s all there if you’re paying attention to the clues.
I think the trailer for this movie does it more justice then most trailers do, these days. It sets you up with a certain expectation of the whimsy and magic of an idealized, romantic concept of a woman, and then dissolves into in a way that makes you see the real, meaningful love Ben has in his life. And when he realizes what he’s been too afraid to contend with (Tabby’s feelings and his own unarticulated feelings for her), he must find a way to break free of Hanna before he loses Tabby, forever.
Beyond this being a terrific Dram-Com that does in a tiresome trope, it’s entertaining, beautifully shot, and a kind film, which is a good thing to have in an increasingly polarized theater atmosphere. The music featured is wonderful, feel-good Motown-era music. In the wrong hands, that’s a terrible cliché; in the case of ENTANGLEMENT, it’s like the right meal at the right time with the right jukebox on in the background. I’m really excited to know that this is one of the first big films Jason Filiatrault has written… it feels like he’s got a lot more to offer.
Without further ado, here’s the interview with Jason James!
Jason James: Hey!
Precious Roy: Hi, Jason!
JJ: How’s it going?
PR: Great—well, sick here and stuck in the snow, but otherwise fine… how are you?
JJ: I’m good—you’re in the snow somewhere?
PR: Yeah, I’m in Atlanta, it’s kind of snowed-in right now, there’s a lot of businesses closed.
JJ: Oh, wow…
PR: We can’t take a few inches of snow over here, it kinda halts everything over here.
JJ: (laughs) Oh, I’m so sorry!
PR: (laughs) …just wanted to say, I really enjoyed ENTANGLEMENT… it reminds me of… hmmm… 500 DAYS OF SUMMER…?
JJ: Yep!
PR: …but it feels like ENTANGLEMENT takes 500 DAYS OF SUMMER even further… it deals with the Manic Pixie Dream Girl trope and does something really interesting with it—
JJ: Yeah!
PR: Is that what drew you to the project?
JJ: Yeah… we’ve seen so many films that center around the Manic Pixie Dream Girl, and this movie, not to give any spoilers, but it takes it to the extreme, where, you know what, that person doesn’t actually exist… and doesn’t exist in this film… and it’s a figment of his imagination. What drew me to the material is that it was just beautiful and fragile and visceral and weird… I read a lot of scripts, and this was something that just felt so honest and it touched me for a number of reasons, even some person ones… it was just a really interesting challenge as a filmmaker, in that it had a lot of visual effects but was also really grounded in character and very honest and real, but fantastical as well.
PR: You really put together a great cast for it, too, they really sold it, especially Diana Bang. There’s a scene in the middle where she’s talking to Ben in front of his fireplace, and oh my lord, that scene was good.
JJ: That was a cool one to shoot! Diana is known as a comedy actor mostly and it was really fun working with her because she would come in with these big, bold ideas, and with that scene, I just kept telling her to go smaller, and smaller, and smaller… and I feel like a lot of times, I’m such a killjoy on set, just telling people to bring it down, bring it down… and that was such a cool process to see where she got to after I beat her up for awhile…
PR: (laughs)
JJ: …but I really loved that moment, I think it’s very simple, and I feel like we’ve all kind of been in that place… that’s a moment in our lives, so we can relate to it.
PR: Yeah… I connected a lot to it… I also like the idea of it all being about delusion and this inability to let go of things in your past
JJ: Mmmm.
PR: …and a hero who has to get to that and realize what he’s doing to himself. Not what external forces are doing to him—
JJ: Yeah…
PR: How hard was this film to put together, in terms of the cast? Did you know who you wanted for Ben, Hanna, and Tabby or was it hard to put them in place?
JJ: I’ve made eight or nine movies now, and this was the easiest one to put into place! It all flows from the script… the script was really just interesting, high-quality material… Thomas Middleditch was the first person on my list… he was the first actor we went out to.
PR: He’s so good in this: likable, relatable, and believable. What made you set your sights on him?
JJ: I like to watch interviews with actors on talk shows and things, to see, kind of, who they are innately, as people…?
PR: Right…
JJ: …and I remember watching this interview with Thomas Middleditch, and the interviewer asked him some kind of inane question like, “what’s your favorite song?”, and he started talking about Neutral Milk Hotel’s “King of Carrot Flowers”, and he just started crying… and I thought, this is totally the character of Ben, who’s either gonna break down and start crying or break down and start laughing…
PR: That is Ben!
JJ: …and he’s just so fragile and emotional, and so, Thomas was the first person we got the script to, and the financing and the other cast all came in around him, and he and I collaborated from a real early-on place, working on the script, playing with tone and the world, and he was just really influential as well.
PR: And how hard was it to cast Hanna?
JJ: It wasn’t too tricky… for me it was more, finding the right tone… I didn’t want to make a 2018 version of WEIRD SCIENCE, where it’s sort of this dream girl, and she’s hot and amazing, and these nerds have created her…
PR: (laughs)
JJ: I was trying to find…. It’s basically about Ben. He’s lonely, and he’s looking for a connection in the world, and he creates this person that he can talk to… and so, I wanted it to be someone that felt real… believable… and have a bit of a dangerous edge, but also sweetness. Jess Weixler is such an amazing actor and she was someone we went out to pretty early on as well, and I remember when I met with Jess, she didn’t want to do it…
PR: Wow…
JJ: She was like, “I’ve read the script, I don’t want to do another comedy, but I thought I’d just have a coffee with you anyways.” And I kind of talked her into it in that meeting…. I was like, “Well, it’s not a comedy, and this is how I see it, and it’s actually, like, fragile, and emotional, and weird, and fantastical…” It was sort of like bringing her around in the moment, so… never take no for an answer!
PR: There are some really funny bits in it, but you’re right, it’s not a comedy, it’s a dramedy-rom that gets you in a sneaky sideways way. I was picking up on the clues, but I didn’t know what they added up to until about the midway point, and I think that’s a perfect time…. I think you’ve done a great job of giving that moment of reveal its proper evolution, from glances Hanna makes at Ben along the way, to some of Ben’s talks with his reflection… and I think the audience will appreciate that, as well… they’re not having an M. Night Shyamalan moment (no disrespect, I love Shyamalan’s work)-- the reveal is not a big explosion, it’s a slow-building bonfire…
JJ: Yeah! Well, it’s interesting… I do a lot of test screenings for my films and I love test screenings, and I asked the audience, “When did you find out that Hanna didn’t exist?” And about eighty percent of the people said, “When Ben finds out, they find out.” And there’s another 20% that find out at different moments along the way… some people earlier, some people at the midpoint… and I don’t think it really matters… I think it’s a satisfying journey no matter where you find out—
PR: Mmm.
JJ: …and it’s kind of a cool thing to look back, and see all the clues…? The little moments? In a slight ‘clubby’ kind of way…
PR: (laughs)
JJ: But, yeah, I think that people come into it… some people are totally lost in the story, and other people are kind of clueing in early… and, you know, It doesn’t really matter… It’s still a satisfying journey.
PR: What do you hope the audience will walk away from ENTANGLEMENT with?
JJ: Hmmm… well, I think the film is really looking at mental health, depression, loneliness… from a really unique perspective… I really tried to get inside of it and show the kind of beauty and heartbreak and drama of that sort of psychosis… and I guess I hope people have a little bit of understanding for all these various stages in our lives, and maybe see a bit of themselves in it, in some way, and recognize where they stand in the whole thing... that’s something I hope you’ll come away with…
PR: Oh, yes... I did… both in Ben and in Tabby…
JJ: I think what’s interesting is that when we screened the film—we’ve played at film festivals for the last ten or twelve months… it’s really interesting to see that we’ve all been touched in some way by mental illness, or mental health issues in our lives… either a loved one, or a family member, or ourselves personally, and I’m amazed at the stories that people have, and how heartfelt and open people are willing to talk to them, and so, yes, I think this film is just an extension of that.
PR: What is next for you—what are you working on next?
JJ: Oh, lots of stuff! Jason Filiatrault (the writer of ENTANGLEMENT) and I have a television series that we’re pitching around, we have a new movie that’s a Fernbank heist film—
PR: (laughs)
JJ: (laughs) –I have another film that I’m doing that’s a road movie, sort of a THELMA AND LOUISE, but at sixty years old… we’re developing a lot of new projects… all in the kind of weird comedy-drama space… and, yeah, just trying to make more movies!
Thanks to Jason James for being such a gregarious interview subject, and thanks for a great film! ENTANGLEMENT is in theaters and On Demand / Digital Friday Feb 9th!
Precious Roy
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