It was close to 8 PM on the night before Thanksgiving in 2019. There was an unusually long line outside of the Southie pub Murphy’s Law, considering how early it was. Everyone was home for the holiday and they were spending part of their evening standing amongst each other on Summer Street. While they might have enjoyed a beer or two (or three), that wasn’t why they were in line that night. They were the friends and family and neighbors of Annie Cheevers and they were there to see her perform.
Growing up in Southie, Cheevers never imagined herself singing at bars throughout town, let alone singing in front of people.
In fact, singing that night at Murphy’s Law was one of the first times she started “singing out,” with The Junction (now Hunter’s) being the place of her big debut.
Stage fright, shyness and internal doubting fears like, am I doing this right? and what do I have to say that’s any good? led Cheevers to hide her talent for so long.
When she was younger, she never thought she could be a singer when she grew up. If anything, she would become some sort of animal activist who continued to petition and hang up posters at the Southie rink that read “don’t wear fur!” Singing was just not in the cards.
Until one night when she was 15 and out with friends and she pretended to have no clue that her friend was recording her singing – we’ve all been there. When the video was posted on Facebook, there was an overwhelmingly positive and surprised response – no one knew that she could sing!
Over the years, Cheevers started to get more comfortable posting short singing videos on social media and the feedback provided reassurement: that she was doing the right thing.
“It took me a while to give myself permission to be creative,” Cheevers said. “It took me a while to be like, you know what, I don’t care, I want to do it anyway, even if I’m really afraid of it. It’s still something I fear, but I think that’s why I want to do it.”
After spending the ‘18 summer working on Martha’s Vineyard and being around the music scene, which to her had an amazing, supportive community, she was inspired to really give the whole singing thing a go.
Four years later, Cheevers has her own EP with four songs, the first of which she titled “Big Kid” and released last week along with a music video.
She describes it as an Indie breakup song about getting over a relationship with a guy who acted like a “man-child” and wanted to make it sound more upbeat and “kid-like” rather than sad or moody.
All of the songs touch on growing up.
“I think the EP as a whole is kind of a tribute to people I grew up with and my family and friends and just the neighborhood, and kind of a love letter in a way,” Cheevers said.
She hopes that all who listen will be able to relate to watching things change in your hometown and growing up in general…and as for that first song, who hasn’t dated someone who acted like a man-child?!
In terms of why the 26-year-old full-time Adult Community Clinical Services community connector and yoga instructor decided to release the music now? For starters, the pandemic allowed her to explore songwriting. She would write the lyrics and her mentor and co-producer of her EP Brendan Little would write the music.
The pandemic also allowed her to finally conquer the guitar…and build up those calluses on the fingers.
“The guitar has haunted me since I was 19. It’s like, I picked it up, put it down…picked it up, put it down…stare at it in the corner of my room, like I know I need to learn you, I really do. It was kind of becoming a beast in my head,” Cheevers said.
The pandemic left her with no excuse, so she started guitar lessons over Zoom with an instructor from Back Bay who she continues to learn from virtually.
Another factor behind putting out her music now is the fact that she is much more comfortable and confident as a performer, although she doesn’t consider herself a performer, rather, a music lover.
She no longer gets stage fright when performing in bars. Initially when she first started performing, she was worried about what the audience would think. Her friend and fellow performer Ryan McHugh once said to her, “who cares if you make a mistake, half the people aren’t even listening.” Now, she sees that as a pressure reliever but also a push.
“There’s something to half the room not listening to you and half the room listening to you,” Cheevers said. “There’s that challenge of, don’t worry, they’re not listening, but could you get them to listen to you?”
If you don’t hear her singing her new song Big Kid, you might hear her singing her karaoke go-tos that consist of the trifecta: Dreams by Fleetwood Mac, Papa Don’t Preach by Madonna and My Heart Will Go On by Celine Dion.
As for where you can see her perform?
Along with the slew of Southie bars, Cheevers is most excited about an event she has this upcoming June at the Brighton Music Hall on Thursday June 9 at 8 PM. There, she is opening for musician Steve Rondo. It’s definitely a pinch-me moment for her, as she grew up going to the music hall and never imagined herself playing her own songs there. She also hopes to play at the Paradise Rock Club one day.
But until then, she will continue her songwriting routine of tidying up her room, lighting a candle and sitting at her desk in a comfy pair of sweats for 30 minutes in the morning, followed by a 45 minute guitar sesh before she leaves for work.
You can watch the “Big Kid” video here and purchase tickets for Cheevers’s Brighton Music Hall show here.
You can download “Big Kid” on Spotify, Apple Music, iTunes, YouTube music, etc