Matilda Aileen Joins Northampton's Music Scene
By Melissa Karen Sances • Photos by Nikki Gardner Studio
Published in Northampton Living | July 2026
Nearly a year ago, we received an email whose subject line intrigued us:
Could she be the next Taylor Swift?
Next came the press release, titled Northampton’s 10-Year-Old Singer-Songwriter Matilda Aileen Debuts Powerful Single Rude Boy on Spotify and Apple Music.
We were hooked. And that was before we’d even heard the song. Even Taylor hadn’t released anything when she was 10.
So who was Matilda Aileen?
On a summery day in May, we met with Aileen, now 11, and her mom Natalie Baker. Baker’s parents also chimed in, but the up-and-coming musician was center stage. In a Zoom call that lasted a little more than an hour, Aileen, who goes by “Maisie” off-stage, endured the jitters that come with being interviewed and relaxed enough to sing bars from her growing catalog of songs, beginning with “Cry Heart Never Break,” penned at age 7 following her parents’ separation.
A rising sixth grader from Northampton, Maisie uses music to put feelings into words. “People always tell you that you shouldn’t think so much about it because you’re so young,” she said, referring to life in general, which has been full of joy and heartbreak. She has had to leave her childhood home, watch her friends get bullied, and come to terms with being a preteen in a society that fixates on appearance.
Luckily, she said, “I always have an opinion about everything.”
While “Rude Boy” came about unexpectedly, she had thought a lot about the bully who had followed her friends, castigating them because they wore glasses and used hearing aids.
“It’s like an anthem,” said her mom of the song. “I think it’s great because we’ve all had bullies in our lives. It’s just like pick your rude boy, whether it’s [an authority figure] or someone on the playground.”
Two summers ago, Natalie and Maisie flew to Nashville with Maisie’s grandparents, who’d booked an Airbnb Experience with singer-songwriter Jackie Bristow, an artist who has toured worldwide and opened for Bonnie Raitt.
In two hours, Bristow and Maisie wrote “Rude Boy” — and, impressed, Bristow asked if Maisie would record it with producer Mark Punch.
You can call me names / You can laugh in my face / But you can’t make fun of my friends / And walk away, sings Aileen.
I feel sorry for you, I really really really do ... You’re just a rude boy / A rude boy / Livin in a lonely world.
The song took a while to reach Spotify, and the morning it became streamable, Maisie was on the bus to camp. Her mom drove over to meet the bus, her counselor called her off of it, and Maisie’s fellow campers watched through the windows while mother and daughter jumped up and down in celebration.
“Rude Boy” has been listened to more than 1,600 times on Spotify and, Maisie said, it inspired the bully to write a rap song about her.
Since then, she has continued singing lessons, picked up the guitar and the piano, played open mics, and collaborated with Morgan-Brown McNeil, who played Orpheus in a Northampton High School musical and is now in college.
Baker encouraged Maisie to approach Brown-McNeil, also a former member of the a cappella group the Northamptones, after seeing them perform at the Iron Horse. The two wrote an untitled song together after plugging three words into an AI generator: mouse, Mars and fiction.
Tear me down in a moment / I’ll run to a galaxy somewhere near Mars / Catch me under the highway / Gathering moonlight and fallen stars, Brown-McNeil and Aileen later sang at the Parlor Room.
For the past three years, Aileen has performed at the Youth Performance Festival (YPF) through the Northampton Center for the Arts.
“The first year, she stood at a microphone and sang a capella; the next year, she played the piano with one hand; and this year she played with both hands and the pedal,” said Baker.
Maisie’s family gets teary-eyed when they recall how far she’s come.
“I don’t really realize how much my family cares about my music — so much that you’re just talking about it and it makes you cry,” she told her mom.
“I think you do know,” she responded. “Everyone who heard your song: It energized them.”
It certainly inspired us.
Listen to "Rude Boy," by Matilda Aileen, on Spotify, Apple Music or any streaming service. Aileen is always looking for local collaborators and recording opportunities. Connect with her at waywillopen@gmail.com.
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