One of the common questions I often discuss with colleagues and friends is how do you rank the Big 4 (Browns, Indians, Cavs and Buckeyes) in terms of your fandom? Sometimes, people included the Blue Jackets as well.
1) Browns -- Growing up in Northeast Ohio, there is a certain degree of self-loathing and being a Browns fan exemplifies this. I just bought the Sunday Ticket package for the Browns and my fiance asked, "Why did you pay $350 to put yourself in a bad mood every Sunday." I didn't have a good response.
2) Indians-- I was a byproduct of those 90s teams. I am still waiting for us to get back to the World Series. I was a poor graduate student during the 2007 run and when the Indians were up 3-1 on the Red Sox, I bought tickets to 6 of 7 World Series games, including airfare to Colorado. Probably the most underrated collapse in Cleveland history. I grew a beard, Al Gore post-2000 election style, after losing Game 7.
3) Buckeyes--I didn't care about Ohio State until attending the University. I remember the 2002 win, but I didn't understand what it truly meant to win a tittle until last year. I truly haven't felt the heartbreak with any Ohio State team like the aforementioned Cleveland teams. I remember watching the Biakabutuka game in 95, but I didn't understand the magnitude of the loss. Unfortunately, 98 was lost on me as well.
4) Cavs---Fun to watch the Cavs, and LeBron moving sucked, but the emotional energy invested in the team is not there for me.
It is hard to root for a hockey team since Cleveland didn't have one during my childhood, except for the Lumberjacks.