Emma Weinswig’s impressive short film “Ben’s Sister” follows a pack of high school boys — including one played by her brother, Ben Weinswig — who make a game of silly challenges for their Senior Scavenger Hunt.
They also award each other points for having sex with female classmates. But their system breaks down when a girl Ben thought was off-limits — his sister, played by Emma — is suddenly brought into their dark play.
The film, which played Friday at the Coronado Island Film Festival, has had a spectacular festival run that included winning audience awards at SXSW and the Nashville Film Festival. It marks Emma Weinswig as a remarkable writer, director and actor with real skill at asking hard questions and letting things play out, however agonizingly.
The film is set in 2015 in California’s Mill Valley, where Weinswig grew up. We asked her about making a darker kind of high school movie, art imitating life, and working with rising star Michael Gandolfini in a different kind of role than he’s typically known for.
Emma Weinswig on Writing, Directing and Starring in ‘Ben’s Sister’
MovieMaker: This starts out feeling kind of like an ’80s teen comedy, or an early aughts kind of comedy inspired by those comedies. But then it takes a serious and thoughtful turn. What were your influences and what were the challenges of executing that skillful turn?
Emma Weinswig: I was trying to tap into the feeling I get when I look back at high school — how it can feel like one minute you’re having so much fun and it feels like you’re invincible and the next minute some shit can go really wrong and fuck your whole life up. Dazed and Confused was of course an influence but I was honestly most inspired by Robert Altman movies that trick you and make you think they’re one thing and then become something entirely different.
MovieMaker: It’s wild and cool that your actual brother plays your older brother in this film. It made me wonder: How autobiographical is this, if at all? Where did the idea originate?
Emma Weinswig: Yes — it is an absolute blast getting work with my brother. He is truly such a brilliant actor and so convincing as “Ben” that sometimes people see the film and think he actually is this character.
While the movie is based on a real tradition that still exists at my high school and is based partially on an experience I had freshman year during the Scavenger Hunt, Ben is not playing himself whatsoever. He is playing an amalgamation of many different guys I grew up around and was always fascinated by and kind of obsessed with. I think Ben is an infinitely interesting character and it’s been so fun getting to continue to explore who he is in the feature version I’m working on. There’s a lot more to see…
MovieMaker: The official synopsis for this describe Ben as a “charismatic fuckboy.” And one of your three previous shorts was called “Fuckboy.” Is there a fuckboy epidemic?
Emma Weinswig: Haha I don’t know… I think a lot of my interest in making movies about them comes from having an older brother and always looking up to him and his friends for what was cool. And then growing up and having unfortunate / stupid experiences with those types of guys and seeing them kind of differently.
And then growing up more and starting to get to know some of those types of guys in a friend way and seeing that they can both be shitty and truly lovely people at heart… I don’t know, it’s complicated.
MovieMaker: I was also surprised to see Michael Gandolfini in this, in a supporting role, and then realized he’s done a few shorts lately. He’s been in several big releases — what do you think made him sign on to your smaller indie film?
Emma Weinswig: Michael is just the best. He was a friend of my brilliant editor and dear friend William Lancaster and as I was thinking of who could be good for the role he came to mind.
I’d never seen him play a character like this but I just had a feeling he could. I still don’t really know why he did it, but I’m so glad he did, because he’s absolutely amazing in it and perfect as that character.
Main image: Ben and Emma Weinswig in “Ben’s Sister.”
You can read more about the Coronado Island Film Festival here and read more of our film festival coverage here.
Editor’s Note: Corrects “Anna” to Emma
