Ryan appeared in his first Brier in 1979 when he was the second for Paul Devlin's Alberta team. They finished 6-5. In 1985, Ryan returned to the Brier, as a skip of Team Alberta. His team of Gord Trenchie, Don McKenzie, and Don Walchuk had an impressive 11-1 performance, their only loss coming in the final against Al Hackner of Northern Ontario. Two years later, Ryan would return to the Brier. His new team, which included Randy Ferbey (whom he played with at the 1986 Canadian Mixed Championship) and Roy Herbert along with Walchuk finished with a disappointing 6-5 record. At the 1988 Labatt Brier however, Ryan's Alberta foursome (now with Don McKenzie as lead instead of Herbert) would win the championship defeating Eugene Hritzuk of Saskatchewan in the final. Ryan's team had a perfect 12-0 record. At the World Championships however, Ryan's team would be undefeated all the way to the final against Eigil Ramsfjell of Norway which he lost. Ryan returned to the 1989 Labatt Brier, which he won again, albeit with three losses along the way. Ryan would this time be able to win the 1989 World Championships, again with three losses. He defeated Patrick Hürlimann of Switzerland in the final. Ryan was nicknamed the Ryan Express for his team's ability to peel rocks which led to many low scoring games, but gave the team two straight Brier championships. This strategy was perceived as boring, and elicited jeering from crowds, and forced the rules of curling to be changed with the implementation of the free guard zone.