Barry was among the NHL's most productive and durable players during the 1930s. He had four straight 20-goal seasons from 1930-31 through 1933-34, finished in the top eight in points every season from 1932-33 through 1936-37 and played all but two regular-season games from 1929-30 through 1938-39. That kind of production and durability earned him induction into the Hockey Hall of Fame in 1965.

The New York Americans signed Barry in 1927, but he played just nine games before being sent to Philadelphia of the Can-Am League (the predecessor of the American Hockey League). He spent 1928-29 in the Can-Am League with New Haven, then got his big break when the Boston Bruins, coming off their first Stanley Cup championship, claimed him in the 1929 NHL Intraleague Draft.

Barry scored 18 goals in his first season with Boston, then had at least 20 goals in four consecutive seasons. He made his first appearance among the NHL's top 10 scorers in 1932-33, when his 24 goals were third behind Bill Cook of the New York Rangers, who led the League with 28, and Busher Jackson of the Toronto Maple Leafs with 27.

On June 30, 1935, Barry was involved in a blockbuster trade that sent him to the Detroit Red Wings along with forward Art Giroux for forward Cooney Weiland and defenseman Walt Buswell.

With the Red Wings, Barry formed one of the NHL's top forward lines with Herbie Lewis and Larry Aurie. He tied for second in scoring in 1935-36 with 40 points (21 goals, 19 assists) in 48 games, then helped the Red Wings win the Stanley Cup for the first time with six points (two goals, four assists) in seven playoff games.

Barry had his highest scoring NHL season in 1936-37 with 44 points (17 goals, 27 assists) in 47 games, was selected to the NHL First All-Star Team and was the first member of the Red Wings to win the Lady Byng Trophy for skillful play and gentlemanly conduct. The Red Wings won the Cup again in 1937, becoming the first U.S.-based team to win consecutive championships.

Barry was tied for fourth in the NHL in points in 1938-39 with 41 (13 goals, 28 assists), but the Red Wings released him shortly before the 1939-40 season and he signed with the Montreal Canadiens. After finishing with 14 points (four goals, 10 assists) in 30 games for the Canadiens that season he was released, ending his NHL career with 387 points (194 goals, 193 assists) in 507 games.

He was a successful junior coach in Nova Scotia for many years before dying of a heart attack on Aug. 20, 1969, four years after being inducted into the Hall of Fame.