Get To Know Madilyn Bailey [Interview]

Kieran Kohorst

Today Madilyn Bailey will be filled with more nerves than excitement as she shares her newest single, one that she’s held on to for the past year with sovereignty over who gets to hear the most personal music she’s made in her career. Now that the song is out of her hands, it can be difficult to relinquish control. Fortunately enough, her stresses can be eased by simply pressing play on her latest release. “Tattoos & Therapy” was written for the chronic worrier, for those who let their anxiety spiral into wasted nights at the club or texts to the one person you should be avoiding. From Bailey’s perspective, there’s much more practical and healthier ways to cope, like putting ink in your skin or talking it out with someone you trust. After listening to the all-too-relatable track - “my alter ego is a grim reaper,” she admits before going into the chorus - you start to trust her judgment more than your own.

When Bailey joins my Zoom room for a conversation about the song and her journey in music, she is quite obviously not in Los Angeles. She’s surrounded by four wooden walls, those of a cabin she is staying in while visiting her home state of Wisconsin. A lot is going on, she tells me, not the least of which being the release of a new single in only a matter of days. Even in the midst of all that is developing in her life, she presents a very focused front with a self-assured demeanor in the face of any question I ask. There are very few stammers or pauses for consideration - aside from one distraction. “Sorry, there’s a deer right outside my window, it's so cool,” she laughs, before immediately getting back to business and offering a quick yet composed reflection of her early career. If the impending release of “Tattoos & Therapy” is looming large over her, the nerves don’t seem to have hit her yet. 

If Bailey was to become overwhelmed in the moment of the single’s release, she would live her lyrics and turn to the more productive coping mechanisms she mentions on the song. For her, it would likely be therapy, or at least the kind of therapy to which she takes best. Her venting is done on a page, penning lyrics that are more than likely to appear on the next pop styling Bailey will record. “I feel like every time I go into a writing session I’m like, ‘mini therapy sessions guys, this is what I’m going through!’” she tells me. “And when I was writing “Tattoos and Therapy”, it was funny because that morning I was having a really manic, panic attack-y kind of morning…I think that being a person who's kind of anxious and manic can be a good thing if you can learn how to channel it properly. You can channel that energy into projects and things you’re passionate about.” Using her anxiety as a superpower, Bailey wrote the only way she knew how. “I went (to the studio) and I’m like, ‘hey guys, I’m feeling super manic today so I think we should just write kind of an anthem for it and how you handle it, how you deal with it.’”

This isn’t the first time Bailey has flipped a narrative on its head. In 2021, Bailey joined the field of America’s Got Talent contenders with one goal in mind: “to sing songs that I’ve written, that I love, and get it out to as many people as possible,” she told the judges as she stood centerstage with her guitar. For her first performance, she chose to sing an original song, one written using only negative comments from Bailey’s YouTube page. The song, as well as her magnetic voice, made a hell of a first impression on the judges. “I love what you stand for,” praised Howie Mandel; “I can’t wait to see what the future is going to bring for you,” beamed Sofia Vergara; Simon Cowell put it most plainly, declaring, “Madilyn, you have a great talent.” Her performance has been viewed over 8.6 million times on YouTube, and Bailey would go on to make a run to the semi-finals of the competition. While her talent and bravery have propelled Bailey into the AGT canon, she has more appreciation for what has come after the nationwide contest rather than the highs of her on-air accomplishments. “I’m really glad I did it, it was such a fun experience. And also, how often do you willingly choose to terrify yourself in that way? There’s so much growth on the other side of being that scared to do something.” With validation from reputable industry voices, Bailey took the lessons she had learned and began to move forward, unafraid to be the artist she had been waiting to become. 

As Bailey began to transition back into her solo work, she was doing so with a bigger audience than she’d ever had before. Some artists experience a sort of whiplash when success comes to them so fast. Bailey was in prime position for an identity crisis, but she didn’t blink in the faces of millions of new fans. For Bailey, it was something she had been preparing for years in advance. “I always wanted it to happen, I pictured it in my head,” she tells me, the deer having just made its guest appearance outside her window. With our impromptu guest out of view, Bailey says that she was “very early on manifesting, I didn’t even know what it was at the time but I had this image in my head that I was going for it. I’m gonna have viral videos on YouTube, this is how I’m going to get discovered. I just knew I wanted to do it in this way and this path and I’m so glad I did.” Essential to Bailey’s path to being discovered was singing covers - “over 100 songs, maybe closer to 200,” she estimates. Altogether, she has officially released 6 volumes of cover performances, beginning in 2012 with acoustic guitar renderings of Nicki Minaj’s “Starships” and continuing today, having shared a piano-driven version of SZA’s “Kill Bill” just over a month ago. Even as she develops as an artist, Bailey doesn’t have any plans on ditching covers. Without them, she wouldn’t be making the music we hear from her today. “I didn’t have a traditional artist development route, like when you go to a label and someone really develops you. I did all of it myself. Covers were so important, an important building block for me learning how to write a song, arrange a song, pick a key, ad-lib, change the melodies. It trained me on how to write pop songs. You learn a lot about what a top hit is and what connective tissue they share.” 

Informed by her past of personalizing ‌music on top of the charts, Bailey has continued to grow and evolve as a writer as she writes some of her most inspired songs to date. The writing sessions that doubled as therapy are most productive for her because “it's when that emotional vein is open when you’re going to get the best stuff.” Sometimes that requires Bailey to show up to a writing session when she’s unmotivated or overwhelmed, but there’s one thing that always leads to results. “Being open emotionally, that would be the thing I make sure I do when I go into sessions. I’m very emotionally open and vulnerable. It’s kind of scary,” she says with a laugh. “At this point I’m good at it.” 

While AGT drew plenty of eyeballs to Bailey, the end of her run meant having to find a way to keep her new fans invested in her. Two years after she appeared on the show, Bailey’s numbers are higher than ever: her Instagram account is followed by 826K people, and her TikTok has amassed 3.2 million followers. The same YouTube account that collected the hate comments used in her AGT debut has 9.6 million subscribers. A quick scroll through her content and her following is no mystery - in her videos, Bailey is candid and wholesome, charming you with her sense of humor on one post and blowing you away with her voice on the next. If it seems like an honest reflection of Bailey’s life and personality, it’s because it is. “I’ll start writing a song and I’m like, ‘oh, I have 20 ideas for TikToks and shorts and whatever,’’' her excitement bubbling just talking about her content. “My brain just works. I write songs, I make content, they go together. I love it.” Listening to Bailey explain her process makes it all sound so simple, as if I could do the same thing and also capture the attention of millions of people. Try as I might, I don’t think I could ever be Madilyn Bailey. 

As Bailey mentioned, none of this is particularly surprising for her; this level of success is something she dreamt about and even planned on happening. That doesn’t mean she’s always prepared to deal with the platform she’s built for herself. “On this side of it, it's actually kind of intimidating. Once you have a lot of success on things, you want to try to repeat it and if it doesn’t get exactly what you’ve already done in the past, then sometimes it doesn’t feel as good,” she says. Even when the expectations are the ones that you’ve built, the weight can be heavy. But whether by the product of a new tattoo or a therapy session between pen and paper, Bailey is able to make peace with the stage she finds herself on now. “I feel like recently I’ve been really enjoying what I’m making so it almost doesn’t matter what it does, the views are almost like a bonus at the end of the day. I’m making the music I love with people I love, with my friends, and I get to put it out whenever I want to. I care less about it even though it's bigger than it's ever been.” Leave it to Bailey to find the light no matter the depth of the dark.

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