My 54 Below Debut & How Taylor Swift Helped Make It Reality

Hi, nice to meet you, I’m Tyler Conroy. You may have a few questions: What’s 54 Below? Who’s Tyler Conroy? and tell me how (Taylor Swift is involved) to make my dreams come true!

On Saturday May 20th, I will be singing at the iconic New York City venue, Feinstein’s/54 Below. Background: if there’s a Broadway performer that you’re obsessed with, they’ve probably sang on this stage; Lin-Manuel Miranda (Hamilton), Alan Menken (songwriter of pretty much every Disney film), Anthony Rapp (RENT), Matthew Morrison (GLEE), Ben Platt (Dear Evan Hansen), and Patti LuPone (literal queen of Broadway) just to name-drop a few.

My friend Rachael introduced me to 54 Below three years ago by making me a YouTube playlist with about 50 videos of performances from the venue and telling me I needed to watch, memorize, and worship every single one of those performers. The amount of hours of my life I’ve dedicated to watching performances at 54 Below is probably embarrassing to admit but I don’t regret a single minute because with every new video (or repeat watch), I just so desperately wanted more than anything to perform on that stage. Now, I not only have the incredible opportunity to put on my own show at 54 Below, “Tyler Conroy & His Broadway Baes”, but I’ll be joined by seven disgustingly talented performers: Giuseppe Bausilo (Hello, Dolly!) Adrian Grace Bumpas, Joey Contreras, DeMarius Copes (Newsies), Matt Doyle (Spring Awakening, Sweeney Todd), Chris Rice (Book of Mormon), and Colton Ryan (Dear Evan Hansen).

A little bit about myself and how this show came to be:

I am probably the biggest Taylor Swift fan…so much so that she even invited me to spend a day with her once but we’ll get to that. Anygay, it started back in High School when I was getting bullied for being different. I turned to Taylor and her music but even more than that, I saw who she was as a person and wanted more than anything to be fearless like her. I started playing guitar and writing songs because I too wanted to turn my feelings into art in hopes that it might connect with someone else and help them the way her music helped me.

Flash forward to senior year high school and I’m in my bathroom recording a song I wrote for Taylor Swift that I then turned into a music video which went viral, got her team’s attention, and scored me a hug & kiss from Taylor herself. In college, I continued to follow Taylor’s career using her music to help me find myself. My junior year of college I wrote her a song to thank her, got the chance to meet her again and had her write “fearless” on an index card so I could get it tattooed on my foot to serve as a constant reminder to stay fearless. Then my senior year of college I directed and starred in the first-ever Taylor Swift musical, It’s A Love Story, written by Dale Murphy (that went viral thanks to the help of Perez Hilton). Taylor couldn’t come to the show so instead, she invited me over to her NYC loft to celebrate the launch of her song “Shake It Off” and the start of the “1989-era”. 

Flash forward to 2016 and publishing company Simon & Schuster was looking for Taylor Swift’s biggest fan to help pen a fan driven biography. So, I did what worked in the past… I wrote them a song basically detailing the same story above depicting why I was the biggest “Swiftie” (that’s what we Taylor Swift fans call ourselves). I won the contest and when the book released last October I put on a Taylor Swift tribute concert in New York City.

(here’s where the 54 Below story starts to begin). In the audience at the show was 54 Below programming director Amy Sapp who contacted me about a month later saying that 54 Below would love to have me bring a show to their venue. It took me about a week to respond to that e-mail because I thought it was fake news. I just couldn’t believe that 54 Below actually wanted me. Me! This small-town boy living in Western Massachusetts who devoted the better half of his life to the church of Swift, to do my own show at a venue I had only ever dreamed of performing at.

But the funny thing about dreams: sometimes they come true if you have the power to pursue them. The entire time I was Swift-ing, writing songs about boys who played me like a guitar, and making vlogs of myself singing my order at the Taco Bell Drive-Thru, I was bringing myself one step towards that dream of mine without even knowing. The best piece of advice I’ve ever been given is that you should do something every day that brings you one step closer to your dream; doesn’t matter how big or small that step is, just make sure it’s forward.

If you’ve ever wanted to witness someone having their dream come true, then please join me Saturday night at 54 Below where you’ll see my dream come true 6x over. But I think most of all, I’m so excited to get to take all Taylor Swift’s teachings and finally put on a show to tell you my own story (ok, there will obviously be a few Swift songs too…).

Stay fearless.





Taylor and her #1 Swiftie (Me!)

Taylor and her #1 Swiftie (Me!)

The Taylor Swift musical that I directed and starred in.