Wynter and Massey made the official announcement subbing in for Arum Wednesday. The show’s topics that evening were a mix of light and heavy: asking listeners whether they prefer blinking or solid Christmas lights, what impact tighter security measures will have on Lenox Mall and Joe Biden’s tone while talking to Black civil rights leaders.
“Shelley and I are both overthinkers,” said Massey, a New York native who has been doing radio for many years including 92.9/Dave FM, 640/WGST-AM and Kiss 104.1. “We had to be told to just do what we do.”
Winter hosted a show in the mid-2000s at news/talk 1380/WAOK-AM and more recently on the now-defunct Talk 106.7. He has only done solo shows before this. “I never thought I was funny,” he said.
“You’re not funny,” Massey interjected jokingly. “Nothing has changed!”
Wynter, an avid supporter of Pres. Donald Trump and self-avowed conservative, would often clash with Massey politically.
“We are so different but the same,” Wynter said. “It’s a lot of fun. The hardest part is subjugating your ego, pushing your ego down to let someone into your world. Once we did that, that’s when the magic really started.”
The show also features executive producer Scotty B and DJ Crystal, who provide extra perspectives.
Wynter said he wants the show to be a bit like friends hanging out at a bar, which is similar to the way Arum approaches his show.
“We are just sharing beers and a pizza,” Wynter said.
“A vegan pizza,” Massey said.
“Listeners are at another table and chime in when they want to,” Wynter added.