It was a sunny afternoon a couple of Thursday's ago, but Printer’s Alley looked like something out of 18th century London. The brick buildings rose high on either side, leaving everything in semi-darkness. Christmas lights and telephone cables stretched across the alley like old-school laundry lines. Interesting characters walked by, asking for spare charge or making a beeline for the strip club.

“This alley used to be the entertainment district of Nashville, back when Andrew Jackson was governor,” explained Stefanie Distefano, a manager at one of the alley’s most popular watering holes, Bourbon Street Blues & Boogie Bar.

She’s right. Back in Jackson’s time—and for more than a century afterward, too—Printer’s Alley was crowded with nightclubs, saloons, hotels and music venues. Many of the city’s first printing companies were located along the alley, and their employees would hit the strip as soon as the workday was over. During Prohibition in the 1920s, Printer’s Alley was one of the few places where locals could still buy liquor. Mayor Hilary House was one of the area’s biggest customers, providing protection for the merchants as well as keeping them in business. “Protect them?” he was quoted at the time by reporters. “I do better than that; I patronize them.”

And so do we. This place is a hidden alley of awesome in a city that’s pretty visible. Why? Well, that's easy. There's always something intriguing to be found...

Sure, we already filled your brain cavities with a few anecdotes about Jackson’s time and Prohibition, but there's so much more history here to discover that's worth mentioning:

• The city’s first car garage was built at the corner of Church and Printer’s Alley.
• The first skyscraper was built nearby, too.
• Hank Williams, Chet Atkins and Waylon Jennings all played at the country clubs that opened up in the 1940s
• And Nashville’s printing business kept the area active until the late ‘60s.

Boo-ya, facts!

Which… could be a good thing? For better or for worse, Printer’s Alley has always been seedy. Nashville’s first exotic dance clubs were located here, and many still remain. The Brass Rail Stables, which currently advertises “nude karaoke,” was once an actual horse stable catering to big-time officials and politicians. The original barn wood can still be seen inside the bar. (Not that we’ve been inside or anything...)

If “nude karaoke” isn’t your thing (although how could it not be?) there are plenty of other joints along this row that’ll quench your thirst for a little libational action with nary a tourist in sight. (Leave that to Lower Broadway; we prefer to raise a glass to the more gnarly ghosts of Nashville’s past at Bourbon Street Blues & Boogie Bar (try the house hamburger, served with pimento cheese and fried green tomatoes), Fiddle and Steel Guitar Bar (especially during the Tuesday night honky tonk jam sessions0, Lonnie’s Western Room (for karaoke with clothes) and Fleet Street Pub (bangers and mash!).

Now? Onwards to nude karaoke! (Just kidding. Kinda...)