Writing duo Dan Gregor and Doug Mand made a name for themselves working on the hit CBS sitcom How I Met Your Mother. Since that series concluded in 2014, they have contributed to the CW’s Crazy Ex-Girlfriend, which stars (and was co-created by) Gregor’s wife Rachel Bloom, who also has a role in their debut film Most Likely to Murder (my review). The film had its world premiere at the SXSW Film Festival on March 12, 2018. I had the pleasure of speaking with Gregor, Mand, Bloom and the film’s lead Adam Pally (Happy Endings) about the film.

Most Likely to Murder sees Billy (Adam Pally, Happy Endings, The Mindy Project), the former most popular guy in high school, return home for Thanksgiving to win back his former flame Kara (Rachel Bloom, Crazy Ex-Girlfriend). After she rebuffs his advances and reveals that she is now involved with former high school weirdo Lowell (Vincent Kartheiser, Mad Men), Billy goes on a bender and thinks he witnesses Lowell murder his mother (they are across-the-street neighbors). With his best friend Duane (played gamely by Mand), he goes on an investigation to prove to Kara that Lowell is a murderer.

The film is first and foremost a comedy, so you might think that it isn’t the type of film that Bloody Disgusting should be covering and you would be mostly right, but I chose to cover the film at SXSW because it shares some DNA with film noir and classic murder mysteries (Rear Window and Disturbia were big inspirations, according to Gregor and Mand).Well, that and I really wanted to interview Rachel Bloom because I stan Crazy Ex-Girlfriend…so here we are.

Story Origins

The idea for Most Likely to Murder had been brewing in the minds of Mand and Gregor ever since How I Met Your Mother ended, but it began with a very simple premise: “We really started because we were obsessed with trying to come up with a story around finding your old VHS tapes with your old pornos,” Gregor said. “It was just something that made us laugh and the inability to find a VHS player nowadays was truly the only aspect of the story we had. We quickly realized there was no movie there. But that emotion of having sort of nostalgia that you are desperate to re-live but unable to actually get back became this sort of emotional cornerstone for trying to tell a story.”

That initial idea did make it into the film, as Billy comes across a VHS tape in his bedroom that contains footage of him having sex with a former classmate (this plays a part in one of the more successful running gags in the film), but the overall plot of the film evolved into something more capable of supporting a full-length feature.

After some more brainstorming, Gregor and Mand widened the scope of their film. Gregor elaborated: “We were like ‘Okay, it’s Thanksgiving weekend, but then how do we make that a more intense, interesting thing so that those emotions are coming through in a much more heightened way?’ That become sort of the puzzle to solve.” Thus, a murder mystery was born.

An Unlikable Protagonist

Billy is a bit of a douchebag, so finding a way to make the audience care about him became one of the bigger challenges for the film. “We wanted him to be a dick and unlikable,” Mand said, “and then we talked with Adam about it a lot. I know one of [his] father’s biggest notes, or at least what he told me, is that we had to make sure that Adam is likable.”

Pally laughed at that, replying: “My dad gives notes a lot. He’s a doctor. But I was excited to play a character like this. I like those characters that are on the border of unlikable and likable because I find that most [real] people are on that border. If you can convey that one way or the other and really make the audience go a second deeper to think about whether or not they like this person then you’ve done your job. Because then you can laugh with them and you can be angry with them. It feels like you get to know them a little more.”

As I stated in my review, your affinity for the film will be based on how funny you find Billy. The film never once tries to excuse any of his past or present behavior, but relating with Billy is a lot to ask of your audience. Luckily, Gregor and Mand’s screenplay has fun with Billy’s dual role of the hero and the villain. “I love that he’s both the hero and the villain of this movie,” Bloom said, “because it gives me something very realistic to play against. As opposed to being the charmingly boyish protagonist who ultimately gets the girl, he’s an entitled ass who actually needs to be taken down.”

Female Raunchiness

Pally may be the star of the film, but Bloom gets her fair share of material to work with as Kara, the straight woman to Billy’s crazy ex-boyfriend (sorry). Not being strangers to using sexual politics in comedy, Gregor and Mand’s script gives Kara one exquisite moment of revenge against the man that jilted her with one raunchy threat involving female ejaculation. It is one of the biggest laughs in the film and not just because it is a woman being crude. “She’s a raunchy girl who fucked the wrong guy,” Bloom said, “and sure there are some things that are gratuitously raunchy that aren’t grounded, you know? Just being like ‘pussy, pussy, pussy’ for no reason is pointless…but saying “I’m going to squirt all over his face” to stick it to someone? It’s raunchy but you’re basing it off of people you know.”

That element of realism is vital to the success of the film and it often prevents the characters from becoming caricatures. “As long as you humanize every character,” Gregor said, “then you’ll be fine. That to me is the biggest thing that I always hope we approach it with. Crazy Ex-Girlfriend does this very well. You just have fully fleshed characters, and you have fun with all of them. Just don’t shortchange your characters.”

You can find out if the film is successful in that regard when Lionsgate’s Studio L releases Most Likely to Murder on VOD on May 1, 2018.