Movie Review: Childish 'Win a Trip to Browntown' Hopes Infamy Sells

Win a Trip to Browntown is one of the most bizarre movies ever made. At once a wholesome family sitcom and a movie that believes anal sex is the funniest idea in the history of man, the very existence of Win a Trip to Browntown boggles the mind. How did any sane person think this was a good idea for a movie? The premise has a man betting his wife with him earning the chance to have anal sex with her if he wins. Who is this movie for?

Win a Trip to Browntown stars a charisma black hole named George A Tramountanas, also the film’s writer and director, as Frank, a professional blogger and wannabe novelist. Frank is somehow paid by people to write an anonymous blog about his life with his family including his wife, Laura (Kendra McDermott) and their three children, Buzz (Gabriel Conrad), Teddy (Manoli P. Tramountanas), and Annie (Eleanor Tramountanos).

Frank’s real passion however, is becoming an author. He has to come up with a pitch for a novel for an upcoming competition called Pitchfest. This might be his chance to launch his writing career if he can find the time to write. How this ends up with Frank and Laura making the bet that drives the rest of the plot is an absolute mystery. I’ve seen this movie and how it gets from one scene to another is a mystery, let alone how they get to the central premise of the movie.

Regardless of the lack of any notable motivation, Frank is overweight and decides he needs to lose weight. In order to provide motivation for her hubby, Laura offers anal sex. Indeed, Laura indicates that if Frank can lose 50 pounds in 3 months, she will willingly engage in anal sex with him. This motivation works, Frank immediately sets out on a diet and exercise program while Laura frets and sweats over the idea that she will eventually have to engage in anal sex with her husband.

This sets up a series of cringe-inducing scenes in which Frank’s friends find out about the bet, via his blogging about it, and become his cheering section and Laura embarrasses herself in ever more humiliating fashion. Poor, poor Kendra McDermott. This lovely woman does everything she can with the kind of flailing energy that you might recognize from any sitcom about boring white cis couples. McDermott is trying very hard to make this premise work and the movie keeps making her look awful.

If you know this movie then you likely have seen the jaw-droppingly awful poster for the movie. It’s not enough for the movie to humiliate McDermott but the poster and other marketing materials has to imply that she has feces stains on her dress from the anal sex she apparently engages in. The movie gives this visual a very different context, but what other context are you supposed to take away from the poster and the premise than that she or her husband has somehow gotten feces on their hands and left fecal matter handprints on her backside.

The marketing and the premise are enough to put off anyone with any good taste whatsoever but the movie itself is plenty repellent. Directed with the amateur quality of a low budget Pureflix movie, Win a Trip to Browntown spends the majority of its runtime as an ostensibly family friendly movie about a quirky family dealing with quirky family stuff like a baby son who wets the bed, a daughter struggling with growing up, and Laura’s struggle to ingratiate herself with fellow mom’s in the neighborhood.

All the while we are watching this incompetent family sitcom we get discussions of anal sex and what a rarity it is. The film’s attitude regarding anal sex is about as sophisticated as a child giggling over something naughty. Anal sex is very funny to the makers of Win a Trip to Browntown and the subject itself is treated as a punchline in and of itself. No need for jokes or clever dialogue, no we are expected to laugh simply because someone might have anal sex.

Meanwhile, the plot spins its wheels through one embarrassing scene after another culminating in our main married couple on stage, in front of their fellow parents and their children, describing their bet in horrific detail with poor McDermott once again humiliated as she’s forced to provide a physical punchline to a non-existent joke. Writer-Director George Tramountanas owes McDermott, as well as his own children, who co-star in the movie and in this scene, a significant apology.

Win a Trip to Browntown is a bafflingly awful movie. Low rent, juvenile and embarrassing to all involved, Win a Trip to Browntown feels like a movie someone made up as an example of a story that would make a terrible movie. The film has the trappings of a bad sitcom and at times it resembles a family movie that just happens to also be about anal sex. I imagine that that juxtaposition is supposed to be funny but like so much of Win a Trip to Browntown, it’s far more confusing than humorous.

Win a Trip to Browntown will be released to on-demand rental services on March 22nd, 2022.