Broadcasting career
After the Colorado Rockies failed to qualify for the 1980 Stanley Cup playoffs, Cherry was hired as a studio analyst for CBC's playoff coverage that spring, working alongside host Dave Hodge. CBC hired him full-time in 1981 as a colour commentator, but he didn't last long in that role due to his tendency to openly cheer for one of the teams playing, especially the Boston Bruins or Toronto Maple Leafs. Instead, Coach's Corner was created, a segment that appeared in the first intermission on Hockey Night in Canada, with Dave Hodge. In 1986, Hodge was replaced by Ron MacLean.
From 1984 to 2019, Cherry co-hosted Don Cherry's Grapeline with Brian Williams, first on CFRB radio in Toronto and its sister stations, moving in 1994 to The FAN 590 and the Sportsnet Radio network. At its peak, the show was carried on over 100 stations across Canada and on several stations in the United States.
For several years he also hosted his half-hour interview show, Don Cherry's Grapevine, which began on Hamilton's CHCH-TV in the 1980s before moving to TSN. His loud, outspoken nature became notorious, and his shows are described as "game analysis, cultural commentary and playful parrying with host Ron MacLean."
Cherry also hosted a syndicated weekly television show called Don Cherry's This Week in Hockey during the 1987–88 NHL season. It featured highlights from the previous week's NHL games. The highlight of each show was when Cherry awarded a Black and Decker cordless drill to the player who levied the "hit of the week" (called the "Drill of the Week" to tie into the cordless drill giveaway).
Branching out from his Hockey Night in Canada duties, Cherry began to release a series of videos called Don Cherry's Rock'em Sock'em Hockey in 1989.
In 1989, he referred to Finnish-born Winnipeg Jets assistant coach Alpo Suhonen as "some kind of dog food", triggering the threat of a lawsuit from Jets owner Barry Shenkarow.
The 15th-anniversary video of Rock'em Sock'em Hockey was released in 2003, with a 'Best Of' released in 2005.
In January 2004, during Coach's Corner, Cherry claimed that players who wore visors were more likely to commit high-sticking infractions. He also said, "Most of the guys that wear them are Europeans and French [Canadian] guys". This statement triggered an investigation by the federal Official Languages Commissioner and protests by French Canadians. CBC consequently imposed a seven-second delay on Hockey Night in Canada. In a subsequent analysis of 82 NHL games for 12 days, CBC Sports Online discovered that high-sticking infractions were committed far more often by players not wearing visors, at a rate of nearly 2 to 1.
Cherry returned to the Coach's Corner for the 2005–06 NHL season without the seven-second delay.
For the 2007 Stanley Cup Finals, NBC decided to feature Cherry in its intermission coverage, a rare appearance on American television. He was partnered with Bill Clement and Brett Hull and it did not conflict with his usual role on CBC as he appeared on NBC during the second intermission.
In May 2008, ESPN announced that Cherry was joining Barry Melrose as a commentator for the remainder of the 2008 NHL Playoffs. He provided pre-game analysis for the conference finals, pre- and post-game analysis for the Stanley Cup finals, and appeared on ESPNews and ESPN Radio. ESPN also announced that he would donate his fees to the Humane Society.
Cherry's commentary was usually peppered with quotables and catchphrases like "All you kids out there...," unrestrained affection for his favourite players (including Steve Yzerman and Kingston native Doug Gilmour, whom Cherry affectionately referred to as "Dougie" and once kissed on-air in a famous TV gag), and overall political incorrectness. He was known for his signature style which included colourful jackets, shirts, and ties he wore during the "Coach's Corner" segment of Hockey Night in Canada.