The Dallas Cowboys, Los Angeles Lakers, New York Yankees and Los Angeles Dodgers are only four of the iconic teams in title droughts.
Montreal Canadiens
The most iconic of all NHL franchises, Les Habitants have won the Stanley Cup 24 times, 23 of them since the founding of the NHL and 22 of them since 1927, when NHL teams became the only ones to compete for the hallowed trophy. The last Cup for the Habs came in 1992-93.