In 2002, Ryan McDonough ’93 found himself the subject of a This American Life episode called “Plan B,” which told the stories of people whose career paths took a left turn. McDonough had wanted to be an actor, but landed at tequila giant Jose Cuervo, traveling to bars around the northeast promoting the drink with party tricks, stunts, and free shots.
As he continued work as an emcee and party promoter, Dreamworks gave McDonough his first taste of screenwriting when it attempted to produce a film version of “Plan B.”
While the idea never made it to the screen, McDonough wasn’t done with film. He began reading about screenwriting, a journey that eventually led him to write his 2021 feature film, Last Night in Rozzie.
“I had been writing for years at that point — usually just an hour free-write, and I used to tie myself to a chair,” he says. “When I was ready to put it towards something, it really helped with the discipline.”
Last Night in Rozzie follows a high-powered New York lawyer’s return to his hometown of Roslindale, Massachusetts, to reunite with his dying friend. McDonough, who grew up in Roslindale, always felt deeply connected to the project.
“Ultimately I decided the story I wanted to tell was a personal one about going home to Roslindale, to Boston, where I grew up,” he explains. “It was just this idea of, what are these kids up to? What happened to the kids I used to be friends with that I never see anymore?”
Writing and producing the film helped McDonough, whose mother struggled with alcoholism and mental health challenges, resolve some of his own childhood trauma. But his personal connection to the story brought its own challenges, too.
McDonough reflected on one scene based on his relationship with his own mother that didn’t ring true with readers. “Learning that truth and believability aren’t the same things when it comes to screenplays,” he noted, sometimes made finding personal resolution more challenging.
Last Night in Rozzie draws on McDonough’s own experience growing up in a low-income neighborhood and eventually leaving for Roxbury Latin, a prestigious prep school in Boston, and Princeton.
McDonough’s Princeton network helped him fund Last Night in Rozzie, an independent film. At times, raising money for the project proved stressful.
“I was really lucky to have people that did believe in me, but there was a lot of work that had to be done to show them what a business plan looks like for a thing like this,” he says. “If I could get people to buy into the movie, then I felt great, and if I couldn’t, I felt horrible.”
His work paid off when Last Night in Rozzie was released in September, winning accolades from various film festivals. McDonough is now working on The Trust, a horror film that follows members of a bankrupt interracial family as they debate inheriting a fortune from the slave trade. He says Last Night in Rozzie gave him the perspective he needed to move forward with screenwriting, his own “plan B” after emceeing and acting.
“The movie became the thing where I learned about business and learned about thinking bigger. Not just following my heart,” he says.
Watch the trailer for Last Night in Rozzie: