When the Wings won their first Cup of what I call the modern, post-Original Six era, it felt like they hadn't won the Cup in forever. It was 1955-1997, 42 years. It now has been 41 years for the Tigers. One difference is that the Tigers have won two American League pennants in the past 18 years, and I do give value to that, whereas the Wings had gone 29 years (1966-1995) between Stanley Cup Final appearances.
When the ground ball went between Buckner's legs in Game 6 in 1986, the Red Sox had gone 68 years without winning the World Series. It has now been 68 years since the Lions last won the NFL championship, in 1957.