Toronto - Despite being the largest market in the CFL, the Argos in recent years have consistently drawn the lowest attendance numbers in the league. There are many reasons for this, but as a Hamilton fan my experience has been that Toronto desperately wants to be New York, they want a second hockey team because New York has multiple sports teams and many feel that they deserve an NFL team and shouldn't have to suffer a bush league CFL team. True Toronto fans are great die hards who love to take and dish out abuse from Hamilton fans. They are tied with Hamilton for the most Grey Cup victories (with 15 although some Argo fans would disagree). They are the Blue Bloods of the league, and I suppose if I compared them to an NFL team it would be the Giants. Oh, and they we originally a rowing club and their double blue colors were taken from the Oxford and Cambridge University rowing teams in England.
Saskachewan - Well if you are a Green Bay fan, you'll fit right in with the Riders. Like Green Bay, they are based in the smallest market in the CFL, they are community owned, they have probably the largest fanbase and they have fanatical fans. In Green Bay, you see the cheese heads, in Regina you see the Watermelon Helmet. Unlike Green Bay though, they have won the cup the fewest times of any team in the league with only 3 to their name.
Montreal - Montreal in the recent years have been the beasts of the east, with their seemingly ageless cancer surviving quarterback, Anthony Calvillo who holds the title of Pro-Football's all time passing yards. They are a team that if you let them get into a rythym, expect a lot of pain. I'd compare them to the New England Patriots, only with a humble QB. The team has folded and come back twice, but all of the teams incarnations have wont 7 cups.
BC Lions - The Lions have always had a strong team, and are the reigning Grey Cup champions. They have a young QB who looks to be the next great CFL qb and the CFL all time recieving yards leader in Geroy Simon. I don't know if there is a team I could compare them to in the NFL, but I suppose the Denver Broncos fit. They have won the cup 6 times.
Calgary - The Stampeders are like the Cowboys (and not just because Calgary is the Cowboy city of Canada), in that every couple of years they have an incredible team and are a force and then fall into being a merely good team for a while. They have won the cup 6 times.
Edmonton - The Eskmios are streaky just like BC, only moreso. The Eskimos hold a North American professional sports record by qualifying for the playoffs for 34 consecutive years between 1972 and 2005 and are the mostt successful CFL franchise of the modern era. They have won the Grey Cup 13 times and are comparable to Redskins of the 80s.
Hamilton - Being from Hamilton I am a little biased, but the Hamilton Tiger-Cats are the oldest current professional Gridiron Football team (although Toronto disputes this fact as the team had two other Hamilton based teams merge into it) and are tied with the Argos for the most consecutive cups at 15 and while the league acknowledges this figure, some don't due to the merging of the old Hamilton Tigers, Hamilton Alerts and Hamilton Wildcats into the Tiger-Cats back in 1950. However in recent years, the team has had a run of bad luck although have begun to turn it around, making the playoffs the last 3 years. The comparisson to the Pittsburgh Steelers is a no brainer.