Jamie Boswell on “Gypsy”

Jamie Boswell

Jamie Boswell is an actor based in New York City, New York. This is his song story…


What is the song and who is it by? 

“Gypsy” by Lady Gaga 

Do you remember the last time you heard it or went out of your way to listen to it?

When I was asked to fill out this questionnaire, I listened to it on repeat for a while on my train ride to Buffalo. 

Do you remember the very first time you heard it? Did you know right away it was going to be an important/meaningful song or did it grow on you?

The first time I heard “Gypsy” was my fall semester of my Junior year of college and I was working on a physical composition (“comp”, for short) for my acting class. The assignment, in short, was to put a song on top of this comp and have it ready for the next class. So, I had been working with this other song (“Elastic Heart” by Sia) and was jiving with it BUT a classmate of mine had found a leaked track from Gaga’s upcoming album, ARTPOP, on Tumblr and raved about it. I listened to it and INSTANTLY fell in love with the track. I dropped the other song without question and used this song instead, it was that right. I was going through complicated, heavily layered feelings about a guy back home at the time. Combined with the stress of school and the show I was in at the time and thinking about life after school, I was just feeling so much (cue the girl who “doesn’t even go here” from Mean Girls). This song instantly struck a chord and stuck with me. It’s one of her best songs ever, in my opinion. 

Fill in the blank: If this song came on at a bar or restaurant I would probably… 

SCREAM on the inside (because it’s not one of Gaga’s better known songs and is never on the radio or Spotify playlists) and then let it sink in…or just sing along!

Do you know how to play the song and have you ever performed it? 

I definitely know the words and can sing along any time I hear it. I’ve never performed it live BUT I want to when I do my one man cabaret. 

If you could put this song at one point in the Lifetime TV movie about you, what would it be and why? 

It would definitely be in a moment where I keep pursuing my dream and my passion and have romance fall to the wayside. 

What is your favorite lyric (or musical moment, if instrumental) of the song and why? 

“I don’t want to be alone forever but I can be tonight…” I think this lyric says a lot. I feel there’s a lot of hope, romance, and dreaming behind it; but at the same time, there’s a slight twinge of cynicism. I think being able to say that you want to share your life with someone at some point holds a lot of power; knowing one’s self enough to accept that something as natural as romance can happen and will happen, but not now, is powerful. 

Fill in the blank: If someone told you “I HATE ‘Gypsy’” you would say… 


How do you feel about other versions of the song? Do you not like hearing anything other than your favorite version or do you enjoy it regardless of who’s singing?

I actually have never heard another version of this song; I’m sure there’s covers out there but I haven’t pursued them. But you can’t beat the original on this one; Gaga’s voice, musicality, and production on the track really lends itself to the storyline and intent of the song. It’s like an epic road trip.

Why is this song so important to you?

This song really has always encompassed my feelings toward relationships and love. As an actor (*cough cough* A “GYPSY” *cough cough*) and having always been a driven/focused individual, having a steady significant other has never been easy for me. I’ve been very focused on my future and what I know I can achieve and what I want to achieve because I love what I do, when I do it. At the same time, it’s human nature to want to be with someone intimately and share life, and I do want that and I know I will. So it’s always been a balancing act for me; one that I have yet to really succeed at. I don’t have Tinder or Grindr or any of those dating apps, I like meeting people in real life; but I’ve always said “When it’s the right time, it’ll be the right time, and I’ll know it’ll be.” 


Learn more about Jamie by checking out his website – www.jamieboswell.com 

If you or someone you know has a great song story, email me at patrickgoespop@gmail.com !


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