In an interview last year with Antithesis Comedy, Winfield said his most memorable performance was at the Baltimore Comedy Factory -- because his mother, who still lives in town, was in the audience.
"Well, she's only seen me a few times performing live, and I don't think she really ever believed that I was funny," he told the interviewer. "So I look up into the crowd and I see her, and she's crying. These are not tears of laughter, these are tears of joy, and love, and motherly stuff. On site of her crying, I begin to get emotional, during a joke that I'm telling about being the victim of domestic violence. I watched the video and I appeared really passionate about the situation at the time."