Cherry played one game with the Boston Bruins, and later coached the team for five seasons after concluding a successful playing career in the American Hockey League. From 1986 to 2019, Cherry co-hosted Coach's Corner—a segment aired during CBC's Saturday-night NHL broadcast Hockey Night in Canada, with Ron MacLean. Nicknamed Grapes, he is known for his outspoken manner and opinions, and his flamboyant dress. By the 2018–19 NHL season, Cherry and MacLean had hosted Coach's Corner for 33 seasons. From 1984 to 2019, Cherry also hosted Grapeline, a short-form radio segment with fellow sportscaster Brian Williams, and also created the video series Rock'em Sock'em Hockey.