What do a Trolley, 80s Outfits, a ton of booze, and a big black lady’s boobs all have in common? Nothing, unless you’re my friend Phortner, in which case they’re all a part of an annual event celebrating your birthday. Last weekend I flew out to Chicago to partake in the Second Annual Awesome 80s Trolley Extravaganza.. Having missed the first one last year, there was no way I was missing this one….

After a harrowing ordeal involving a cancelled flights, six hours sitting in an airport, four hours sitting on the tarmac, an obnoxious cell phone lady who talked the whole time (4 hours, seriously?), and screaming babies (again, 4 hours, seriously?), we finally made it to Chicago. With almost 27 hours of travelling under our belt, we felt worn, beaten, and defeated, but our spirits quickly lifted as we realized Trolley Eve was upon us.

We spent Friday night partying and catching up with other friends in Chicago, and regrouped for brunch on Saturday to discuss the plan for the day. Later, we hit up the thrift store to finish putting together our outfits. And not just any old thrift store (where the economically disadvantaged can find discounted wares), but the sort of thrift store that caters to young adults looking for trendy, punky, hipstery, whatever-else-y outfits. The sort of place that makes my oft-striped-shirt-wearing-yuppie self feel a little out of place.

We picked up the digs, and headed back to the apartment to start getting ready (and start boozing). In the evening, the rest of the guests started to arrive. The costumes were ridiculous - 80s prom queens, a Bruce Springsteen fan, an AC/DC fan, a girl wearing 80s formalwear (sequins everywhere!), a creepy guy with a mustache, 80s punks…the list goes on. Neon. Hair spray. Slap bracelets. Yes, thats right, slap bracelets (the birthday boy ordered a bunch as party favors).

We loaded up the trolley with booze and set off on the extravaganza, which in a nutshell involved drinking on the trolley interspersed with drinking at bars. There were also seperate guys and girls walkoffs (set to Michael Jackson - Beat It, of course) and best costumes were decided.

All aboard!

Rock on Birthday Boy!

And now the part of the story you’ve all been waiting for… The itinerary for the night included a pit stop for food at one of Chicago’s famed places for drunken eats, The Wiener’s Circle. Essentially a shack with a parking lot, this place is not famous for the food, but instead the attitude that comes along with it. The all-black staff literally shout at you, curse at you, make fun of you, and eventually serve you your food. Its most funny when people join in and start shouting back (although one friend of mine is under a self-imposed ban for getting too into it and making an ‘underground railroad’ comment).

One of the most popular items on the menu is the Chocolate Milkshake, and if you read the first sentence of this post, you know where this is going. For $10, you and everyone else within eyesight can experience the wonder horror of this. In our case, the charge was $20 (because we were such a big group), and it went a little like this:

Person 1 goes to the back somewhere and starts flickering the lights.
Person 2 grabs a spatula and starts shouting and banging the metal counter
Person 3 lifts up her “Baby Girl” shirt and starts bouncing her tits around

No matter how drunk you are, there are some things that you just can’t unsee.

I’ve seen her tits…

I actually have video of this as well, but for now I am not going to post it online. If you know me, you can come over and watch it…if you dare.

Anyway, the last stop on the Trolley was a bar that featured Karaoke. Put 30 drunk idiots together in front of a microphone and what do you get? A terrible rendition of Come On Eileen that has Dexy and her Midnight Runner’s rolling over in their graves (if they’re dead…I have no clue).

After the party was the afterparty, back at Phortner’s apartment. My memory is all bits and pieces from here, but I do know that a New Kids On The Block sleeping bag was involved.

While visions of trolleys danced in his head…