October is, without question, my favorite month of the year. The weather in the Midwest—where I've lived for all but seven of my falls—is perfect, football is finally in the swing of things and there's a baseball playoff game almost every night. This fall, though, takes it to a new level. It was 70 degrees in Chicago on Sunday, and the Cubs are playing the Indians in the World Series, a matchup that has me wondering if sports just aren't the greatest thing ever—or if the world might be ending.

Regardless, in that October spirit, I've decided to take some inspiration from the two teams playing in the Fall Classic. It's been 71 years since the Cubs so much as appeared in a World Series, 108 since they won, and the Indians haven't seen much better luck; they last won in 1948 and haven't appeared for 19 years. With that in mind, I've decided to take that theme across sports and rank the five longest-suffering football fan bases. There's no group quite as beleaguered as Chicago's North Siders, I don't think, but some poor schmucks do come pretty close.

*A note: These rankings are, as you might guess, purely subjective and are correct only because I decree them as such. I weighed several factors in determining this list, though, including years without a bowl berth, scarcity of bowl berths, big losses, fans' dedication, other talented teams in different sports at the same school and near-misses. Also, I decided to restrict my list to Power 5 programs because, well, there are just too many college football teams.

So without further ado, here are some quantifications of sadness. Trust my opinion. After all, I grew up a Missouri fan.

5. Purdue

Purdue hits a lot of my basic metrics here. It hasn't been bowl eligible since 2012, and only five teams have worse winning percentages than the Boilermakers (.386) over the past 10 seasons. Since 1952, Purdue has won just two Big Ten titles (that's one every 32 years over that stretch, on average), and it hasn't finished a season with double-digit wins since 1979. Having a solid basketball team has to help Boilermakers fans cope—as does the name Drew Brees—but the situation is still pretty dreary. At 3–4 so far this season, Purdue has been okay, but a bowl berth is definitely still a long shot, and with coach Darrell Hazell already fired, it'll also be time for the program to hire its third new coach since 2009 come winter.

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4. Colorado

The Buffaloes are on this list in large part because of what once was. In the early 1990s, they were a premier Big Eight program and even won a national championship in 1990. The team remained a power until 1997, at which point things got very mediocre and then eventually very bad. At 41–90, Colorado has the worst winning percentage (.313) of any Power 5 school over the past decade, and it also has the longest active streak of missing a bowl game, dating back to a 2007 Independence Bowl loss. Still, you can't feel too bad for Colorado fans; Boulder is one of the best college towns in the country when it comes to scenery, weather, food and, um, diversions.

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3. South Carolina

For a team that seemed to hover around the top 25—or at least play competently—during the Steve Spurrier era, South Carolina has surprisingly little to show for it. The Gamecocks finished ranked in each year from 2010 to 2013, but since joining the SEC in 1992, they've never won the conference and have just one division title to their name (in 2010 when they went on to lose to Auburn in the SEC Championship Game and to Florida State in the Chick-fil-A Bowl. South Carolina also gets extra points here for having to deal with its in-state rival, Clemson, surging over the past few seasons and also for a lackluster basketball program that hasn't appeared in March Madness since 2004.

2. Missouri

Let me tell you how much it pains me to relive everything I'm about to write. But I'm doing it for you guys because it must be done. Let me begin by reminding you that Missouri once lost a game because its opponent was given a fifth down. Let me also add that in 2007, the Tigers were briefly ranked No. 1 in the country and won 12 games but missed a BCS bowl berth because the geniuses in charge of the selection process thought Kansas and Illinois—two teams Missouri beat that year—were somehow more deserving. Really, my current blood pressure alone should be enough to get the Tigers near the top of this list, and I haven't even gotten to the fact that they no longer get to play their biggest rival because of conference realignment and general obstinacy, and Gary Pinkel got cancer, and this year's team just lost to Middle Tennessee. Okay, I think you've maybe heard enough. Thank you for this platform. I'll return to something approaching sanity before I crown college football's king of futility.

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Which is…

Without further ado…

Wait. I should qualify. This was hard. In the end, I found one flaw with some of the more obvious programs. They all have great basketball teams. So I'm sorry Kansas. I'm sorry Indiana. I'm sorry Kentucky. You all have hoops, and while I'm sure plenty of your fans might prefer football in a perfect world, I'll let them cry all over your trophy cases.

So actually…

1. Iowa State

The Cyclones have a .323 winning percentage over the past 10 seasons, second only to Colorado for the Power 5's worst mark. Yes, still worse than Kansas. Iowa State also hasn't made a bowl game since 2012, has only made eight bowl games since 1990 (just five teams have made fewer over that span), and in those bowl games, it's gone 3–5. Sure, it's had some basketball success in recent years, but it's golden-boy hoops coach also bolted for the Bulls, and its football coach, Matt Campbell, is the school's third this decade. The Cyclones also get points for the relative boredom of their location—don't get me wrong, I love Ames, but there's not much else to do besides attend sporting events—and the dedication of their fan base, which really, truly seems to care about the school's teams.

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