In 1993, there was his cocky "you can't beat me" wink at Tomas Sandstrom of the Los Angeles Kings in Game 4 of the Stanley Cup Final with the Canadiens on their way to their 10th consecutive overtime victory en route to the championship.
In 1996, with Colorado, reacting to the playoff trash-talking of Chicago Blackhawks forward Jeremy Roenick, Roy said through his crooked grin: "I can't really hear what Jeremy says because I've got my two Stanley Cup rings plugging my ears."
Roy would add another ring that season, and one more in 2001, having won his first with the Canadiens as a 20-year-old rookie in 1986, his second in Montreal in 1993.
Tremblay hadn't heard about Roy's resignation Thursday afternoon when I reached him, offering a "no comment."
A stony silence between the two men ended a few years ago at the golf tournament of Canadiens coach Michel Therrien.
On March 18, 2014, Roy returned to Montreal's Bell Centre for his first game in the city as coach of the Avalanche, before which Tremblay spoke with former Canadiens enforcer Chris Nilan on the latter's Montreal radio show.
Tremblay recalled that he had asked Roy after the first period of the legendary game against Detroit whether the goalie felt well after having surrendered five goals.
Told by Roy that he felt fine, Tremblay put him back in the net.
"The mistake I made [is that] I should have pulled him out after the seventh goal," Tremblay told Nilan. "But I don't think Patrick should have reacted the way he did. There's always a time to talk with the coach, talk with the GM. [Roy] made a mistake, I made a mistake, so let's move on."
Both men have done just that.
Roy's No. 33 was retired by the Canadiens during an emotional ceremony on Nov. 22, 2008. During it, a five-minute standing ovation was accorded to the man known in Quebec as Saint Patrick. A dozen pint-sized goalies skated onto the ice wearing NHL jerseys bearing the names of Quebec-bred goalies, a tribute to Roy's influence in developing goaltenders in his home province.