I was an army brat, so grew up in quite a few places, notably El Paso, TX (blech), Honolulu (yes it is amazing), San Diego (beautiful, laid-back beach town). But I spent my most formative years (teens) in wonderful
Leavenworth, Kansas.
Leavenworth's best claim to fame, by far, is Melissa Etheridge. But besides that, we have the fantastic notoriety of being host to 5 (count em, 5!) prisons.
1. Maximum security federal prison - Leavenworth (yes, you've probably heard of it in movies and whatnot)
2. Kansas State Men's Penitentiary
3. Kansas State Women's Penitentiary
4. US Army Disciplinary Barracks
5. Kansas State Juvenile Facility
Here's the Fed. Famous (or infamous) prisoners include(d) Leonard Peltier, American Indian political prisoner; Bugs Moran and Machine Gun Kelly, depression-era gangsters; and now the new home of Michael Vicks, NFL quarterback convicted of running a dog-fighting ring.

Yes, the whole town felt like one huge dark hole. For such a small town (around 35,000 people, not counting the prisoners

) there was an amazing amount of drugs, guns, and gang-related activity. Now the town is basically one massive crystal meth sinkhole, and people are leaving like crazy.
Really, a wonderful place to spend those formative teenage years. Just glad I survived!