The Ugly American: Hookertown and Killerville

I have an affinity for towns founded by bootleggers and whores. I’m sure I’m not alone. Show me one person who can resist a place that touts its most famous resident as a murdering conman soap salesman, or one with a cemetery containing a prominent gravestone that proclaims, “Minerva Downs, Negress Brothel Owner.” Towns like this are almost exclusively found in the U.S., seeing as how the gold rush brought the dregs out to establish the places before any foundation of civil order. Following are six of my favorites:

Skagway, Alaska
A town built around brothel/booze halls like the popular Red Onion Saloon, a smoky shanty steeped in whiskey, blood and phlegm (probably). In the late 1800s, the saloon advertised shady ladies “Five bucks for 15 Minutes” to cash in on the throngs of prospectors choking the area during the gold rush. The saloon still stands today, crowded with cruise passengers on stopover. The prostitution and gun-slinging are gone, but the booze still runs freely.

Tombstone, Arizona
Residents regularly shot the crap out of each other while prospectors founded this tiny lawless speck of an outpost just south of Tucson. The place is only three blocks long and looks like a prop set for a spaghetti western. A gaggle of costumed characters roam the dusty streets, self-appointed ambassadors to Doc Holliday, Wyatt and all the other Earps, not to mention the Clancy brothers, whom they killed during the famous gunfight at the O.K. Corral. All the old colorful saloons are still there, as are all the old whorehouses, which have all been converted to colorful saloons.

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Las Vegas, Nevada
When I was a kid visiting Vegas with my gambler mom, I once found a menu from the famous Nevada Chicken Ranch detailing the prices for certain acts of the illicit variety. I remember thinking that $200 for a tandem tongue bath sounded pretty cheap. Today the Chicken Ranch is still there, 60 miles outside Vegas, but it’s the debauchery of downtown Vegas that mesmerizes me. All the old mummies rolling around in their Rascal scooters are probably people who came a hundred years ago and got trapped in a perpetual vortex of cigarette smoke, free hooch, horrible buffets and easy poontang.

San Francisco, California
During the gold rush this place was so dangerous the policemen were even afraid to walk the streets. Drunk revelers would pass out and wake up getting whipped on a ship to Shanghai. The Barbary Coast was a hotbed of whore houses and gambling halls, as 49ers flooded the city at the turn of the century. All this plus a creepy giant prison looming atop a rocky island just off the bay. Even all the present-day Silicon Valley upyucks can’t keep me away.

Ketchikan, Alaska
The famous Creek Street is a former boardwalk lane containing a collective of bawdy houses owned by entrepreneurial madams, the most famous of which was Dolly Arthur of Dolly’s House. She died not too long ago, in a big brass bed with satin covers, surrounded by 20 dogs.

Port Royal, Jamaica
This port town doesn’t really exist anymore except for what’s underwater right off the coast of Kingston, but I still think it bears mentioning. Founded by pirates and privateers (aka criminals), this place was a festering free-for-all of murder, thievery, prostitution and smuggling. It was the inspiration for Disney’s Pirates of the Caribbean. In the 17th century, Port Royal was considered the most “wicked, lewd place in the Christian world,” which may or may not explain the massive earthquake that sank it into the sea in 1690.

Hollis Gillespie writes a weekly travel column for Paste. She is a writing instructor, travel expert and author of We Will be Crashing Shortly, coming out in June. Follow her on Twitter.