In 2020, the COVID-19 pandemic shut down movie theaters across the country for months, and when they finally reopened, the industry had sustained damage that would take years to recover from. But the global crisis didn't just impact Hollywood via cinema closures, it essentially ground production to a halt, with the industry shuttered for much of the year. It wasn't until very late in 2020 that any new studio productions went before cameras, and one of the first featured Dean Winters.

Always on the lookout for a movie role, Winters took a part in "Christmas vs. The Walters," an independent holiday movie starring Shawnee Smith ("Saw"), Bruce Dern ("The Hateful Eight"), and Chris Elliott ("Groundhog Day"). When it began filming in November, the pandemic was still raging and vaccines were still weeks away. The production, which took place on Long Island, utilized plenty of safety precautions, including mask-wearing during rehearsal and regular testing for coronavirus among cast and crew.

Making the movie was "challenging," Winters said when he spoke to TV Meg alongside Shawnee Smith. According to Smith, the weather wasn't helping matters. "You can't really rehearse like that," she said. "I mean, you do the best that you can, but all the windows and doors are open for ventilation, and it's November. In November in New York, in Long Island; you're freezing." Despite all the hurdles, the film was completed and got a limited theatrical release the following November.