18 Questions with Madilyn Bailey

18 Questions With introduces 1883 readers to the brightest young artists, actors, creatives and beyond. From childhood memories and guilty pleasures to their latest ventures and upcoming projects, our goal is to bring you closer to the people who inspire and entertain us. 



Rising pop singer-songwriter Madilyn Bailey first made her mark in 2021 for her clever viral bit for an audition for America’s Got Talent, where she wrote an original song made up entirely of hate comments left on her Youtube channel. However, with her brand new single “Tattoos & Therapy,” she proves that she’s more than the girl that went viral on a singing competition. The track is the perfect blend of uptempo pop production and a catchy hook, but lyrics rooted in honesty. Boasting more than 15 million fans across all of her social media platforms, Madilyn Bailey is one to keep on your radar.

To celebrate her new single “Tattoos & Therapy,” Madilyn Bailey chats with 1883 about her favourite childhood memory, what inspires her to write, and more. 


What’s one exciting thing that happened to you this week?

My new song “Tattoos and Therapy” came out this week! Go stream it wherever you listen to music!


What was the last thing you read?

I’m currently in the middle of reading Fourth Wing. So Good. What are your thoughts?


Favourite memory growing up?

I think it would be the first time I sang in front of people at my school talent show. I was so nervous but everyone was so supportive. It was definitely the start to all of this! 


Where was the last place you traveled to?

I’m currently replying to these questions from a lake house in Wisconsin! 


What was the last thing that made you laugh?

I was doing an interview today when a deer walked by my window, squatted down and started peeing… very distracting but very funny… I also didn’t know they squatted to pee… news to me! 


What’s your night time ritual?

My night time ritual is skin care, jammies, and reading (but if I’m being honest sometimes I watch TV instead of reading)


Who would be on your dream dinner party guest list?

I know you’re supposed to name some celebrities here but that gives me major social anxiety even at the thought of it sooooooo my dream dinner party would be just with my friends and husband!


Favourite quote from a film or TV show?

I literally cannot think of a quote right now but if I could it would be from New Girl or The Office!  


What’s your go-to karaoke song?

Call me the grinch but I hate karaoke… the songs are never in my key!


Favourite item in your closet?

I love my Naked Wolfe Tennis Shoes! I call them my “going to battle shoes” because they make me taller and give me an instant confidence boost. 


Can you tell us a little bit about your new single “Tattoos & Therapy” ?

Have you ever wondered what a panic attack in the form of a song would sound like? No, well this song is all about that nasty self destructive spiral that can happen when having extreme anxiety or a panic attack and offers an interesting alternative… You guessed it: “Tattoos & Therapy”!  


In your opinion, where is the best place for fans to listen to your new single for the first time? 

Oh, I think the best place to listen to this song would be in the car with the volume loud or somewhere where you can dance around… you might get the urge to break out some moves! 


Is “Tattoos & Therapy” the first of many songs to come this year? Do you have any plans for an album? 

I might….


What inspires your music? 

My music is heavily inspired by my real life experiences. My struggles, my fears, my triumphs and my failures.  


Is there anything you do to mentally prepare for a writing session? 

Writing sessions feel a bit like a therapy session so really the only thing I need to do is go into it with an open vain to my emotions and a willingness to be vulnerable.  


Describe your music in 3 words.

Almost embarrassingly honest.


What songs do you currently have in rotation?

Taylor Swift mostly. I just click “Taylor Swift complete collection” playlist on Spotify, randomize the selection and boom T Swift all day… I have a problem but also somehow I have no tickets to the Eras tour.


Career wise, what are you most proud of?

I’m most proud of my resilience whether it be outsmarting the haters or keeping up with the ever changing terrain that is the world of social media or the many evolutions I have gone through as an artist. I have come a long way and I’m the most confident version of myself today because of it. 


Listen to Madilyn Bailey’s latest single “Tattoos & Therapy” HERE


Interview Rachel Martin

Photography Jade Ehlers

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