The Boston Bruins and Montreal Canadiens will write another chapter in the NHL’s most historic rivalry when they meet Thursday night in Game 1 of the Eastern Conference semifinals.

This will be the rivals’ 34th meeting in Stanley Cup playoff history, more than twice the amount of postseason series between legendary NBA rivals the Boston Celtics and Los Angeles Lakers.

Before we begin what promises to be another all-time classic, let’s take a look at the most memorable Canadiens villains from the 90-year history of the Bruins-Habs rivalry.