I've got it narrowed down to these three, and here's why:
Some states are boring in the sense that they have very small populations, like Wyoming, Montana, or Alaska, but they have other things going for them: Wyoming has a history as being the classic cowboy state, and it was the first place in the modern world that gave women the right to vote (unbelievable, right?). Montana and Alaska, though they may not have big cities with exciting nightlife, have breathtaking scenery (at least in certain places, and enough of them to count).
Some places have monstrous histories and are backwards in many ways, like the Southern states as well as Indiana and Kentucky, but these characteristics at least make them interesting (and despite their histories of terrible racism, slavery, and torture, the South is the most racially integrated region of the United States today). Civil War battle grounds, for example, give these states a connection to some of the most important and well-known history in America. So if nothing else, these places have interesting histories.
But Delaware, Nebraska, and North Dakota? What's interesting about these states? Okay, Delaware is the state of incorporation of most Fortune 500 companies, mainly due to their lax corporate laws, but these companies do very little business there. On the whole, the state is bland as can be. Then there's Nebraska and North Dakota. Kansas is boring as hell too, but it has a history of being home to some of the most nortorious and violent outlaws in the West. Same goes for Oklahoma; plus there's the whole Dust Bowl saga and the state's reputation as the quintessential Depression-era state (not good, but interesting). South Dakota has the Badlands, Mount Rushmore, the Black Hills, the Jewel caves, Deadwood, etc. But North Dakota? Their Badlands, though pretty, aren't as moonlike and sparesly beautiful as those in South Dakota, where you can look out and feel like you're on a desert planet.
Okay, so what do you think?
And I want to make clear that I don't think there is anything wrong with these states, that they aren't nice places to live, and that individual communities within these states might have interesting histories and local legends. But on the whole, they aren't very exciting or interesting.

