NHL: Montreal Canadiens were a powerhouse for decades and decades . . . not so much in the past 20 years. I'd have to give it to the Red Wings currently.
"Most Successful" is a tough call. Certainly the NYY in baseball but perhaps not the Celtics. They've won 17 or 18 championships and the Lakes have won 15 and definitely the last 30 years it's been the Lakes better than anyone.
NFL? Yeah, I think you gotta go with the Steelers due to winning in the 70s and 2000s. However, the 'Boys are right up there, winning in the 70s and 90s and challenging in the 2000s.