re: What's the most depressing bowl game?

I can't give you one answer, because there's so many of them. So I guess I'll just list them in no particular order. By the way, App State and Toledo isn't a bad matchup IMO, but Montgomery is an awful place for a bowl game.

Famous Idaho Potato Bowl: Idaho vs. Colorado State -- Boise might not be a bad town, but you're spending a late December night in Idaho. Not in Miami, San Diego, or even Houston. Idaho. Plus the matchup is a snoozer, with Idaho (about to turn FCS in two years I think) and Bobo's Boyz

Lockheed Martin Armed Forces Bowl: Louisiana Tech vs. Navy -- The whole Dallas/Fort Worth area is just boring. And I feel so bad for Navy. They could have been playing just down the road for the Cotton Bowl, and now they are stuck with playing LA Tech in an early bowl game.

Dollar General Bowl: Ohio vs. Troy -- Who the frick is going to proudly hang up a trophy in their office from the Dollar General Bowl? The matchup isn't horrible but if I was a player I wouldn't know whether to laugh or cry when I found out I was playing in the fricking Dollar General Bowl.

Quick Lane Bowl: Maryland vs. Boston College -- As another poster stated earlier, watching two small schools play at least involves some level of excitement and gratefulness to be there. But two power five teams that simply suck? Sign me up for that every time! Plus I hear Detroit's pretty nice in late December. Hopefully both fans attending the game stay safe.

New Era Pinstripe Bowl: #23 Pittsburgh vs. Northwestern -- Poor Pitt. You have the best two wins in all of FBS. Beating Penn State and Clemson, just so you get the great privilege of playing a 6-6 Northwestern team.

Nova Home Loans Arizona Bowl: Air Force vs. South Alabama -- I'm usually pro-lots of bowl games, but when your game is being broadcasted only on the Arizona Sports Network, you've got too many bowl games.