Roberts won two Stanley Cups with the Pittsburgh Penguins in 1991 and 1992 and became the first American player to appear in 1,000 NHL games, in 1992. He played for the Boston Bruins during his final two years in the NHL, then played two more seasons in the International Hockey League before finally retiring at age 39 in 1996 -- the last of Gordie Howe's old teammates still on the ice. (Incredibly, Howe himself still wasn't done as a player, making a cameo appearance with the IHL's Detroit Vipers in 1997, at the age of 69.)