The cover of Anna’s delightful EP, “Casting Barely a Shadow.”

By Len Lear

Anna Shoemaker, 22, of Chestnut Hill, is a terrific singer/songwriter who has entered the cauldron of the music industry that can chew up and spit out singers as if they were after-dinner mints. But Anna, who triggered lots of positive vibes when she performed her “dark pop” every week last summer at El Poquito, is going to have an entry on her resume this coming weekend that not many musical hopefuls can boast.

That’s because Anna will be performing June 15 to 18 at a huge outdoor event in Dover, Delaware, called the Firefly Music Festival. If you go on their website, you will see Anna’s name among the performers, and at the top of the list you will see the headliners, including the legendary Bob Dylan, The Weeknd and Chance the Rapper, among others.

“This is a, crazy incredible opportunity,” Anna told us last week. “I’ve been working with this artist collective, REC Philly. Last fall they asked me if I’d be interested in playing Firefly, and obviously I was interested, so eventually they asked me to play on their stage. It’s really exciting!”

So how does Anna feel about playing on the same bill with Bob Dylan? “So ridiculous, I grew up listening to him (my mom is like in love with him), so it’s just crazy! … I’ve been writing songs and singing since I was so young, so it just feels all very natural for me. It’s not like there was a time when I woke up and was like ‘I am going to be a musician!’ but I guess I’ve always known that I’d have to do something creative so I have a place for my emotions. I can be hyper-emotional sometimes, for sure.”

Growing up in Chestnut Hill, Anna went to Springside for a while and then transferred to a boarding school in Northeastern Connecticut for most of high school. She just graduated college last month from the University of Colorado at Boulder, majoring in English and minoring in women’s studies.

After graduating from high school, Anna started playing in coffee shops, random bars and open mics in Philly, “really anywhere that would let me and then when I moved to Boulder, I began doing the same thing there.”

After living in Colorado, why did Anna move back to Chestnut Hill? “I actually love Philly. I really missed the fast-paced east coast mentality in general while living in Boulder. My only complaints about being here would have to be with SEPTA when they’re not running on time.”

Anna has a smoky, sultry, funky sound, reminding me of blues singer Susan Tedeschi, but Anna has always looked up to other female singer/songwriters like Amy Winehouse,  Fiona Apple and Banks. (Jillian Rose Banks, known simply as Banks, is a singer/songwriter from Orange County, California.)

“I grew up listening to Sheryl Crow, Alanis Morisette and Lucinda Williams. I’m not really sure who I sound like out of them, but I’m hoping to create a dark pop vibe.” (You’ll see what she means if you check out her song, “Bitch, Don’t Kill my Vibe,” on YouTube. My favorite line in the song is “I’m a sinner, prob’ly gonna sin again.”)

What are the pros and cons of trying to make it in the music business? “For me it’s just letting go of my music and actually putting it out. I am sitting on so much content just because I want to make sure everything is perfect. It’s a character flaw really more than anything to do with the music industry. It’s just hard because my music is very personal, so putting it out in the world on the internet has been really difficult for me. I definitely do better playing live because it’s easier for me to convey the right emotion behind the songs.”

What was Anna’s favorite gig of all time? “This past spring break, my best friend and I went to Vancouver, B.C., and I played two really fun gigs there. I just really like getting in front of different crowds and getting out of my comfort zone. It’s easier for me to play in front of people I don’t know. I feel like I have a lot more freedom in those situations.”

What was Anna’s least favorite gig? “I played this one coffee shop when I was younger, and it was super far from Boulder on like a Wednesday night, so no one but my best friend showed up. It was pretty sad, but I did it anyway!”

Anna has produced a terrific EP entitled “Casting Barely a Shadow.” She hasn’t released any CDs yet, but she is currently working on putting together a project “that I am really excited about.”

How does Anna feel about the current pop music scene in the U.S.? “I’m just really inspired by the number of female singer/songwriters on the rise.”

Who are her own favorite singers and songwriters, living and/or dead? “Amy Winehouse, Johnny Cash, Mitski and SZA.”

What is the best advice she ever received? “My dad gives really good advice. Last night, for example, he told me that if you are honest and upfront with people, either they will do the same, or you will easily be able to detect their bullshit.”

Who are Anna’s heroes in real life, living and/or dead, in or out of the music business? “I’m really inspired by anyone who stands up and goes after their passion or dream, regardless of what other people think. I think there need to be more people in this world who do things because they WANT to, not because they feel like they HAVE to.”

In her spare time, Anna relaxes with her family and dogs — Winnie, an English Bulldog, and Maisy, a Jack Russell Terrier — and goes to a concert here or there. “College took a lot out of me,” she said. “I’m all partied out … Right now I’m really just focused on finding good people to work with, laying down songs and securing this vision I have for my music.”

What is Anna’s biggest pet peeve? “LOUD CHEWING! It grosses me out so much, you don’t even know; ask my sister. Also I hate bad drivers, probably because I’m a terrible driver, so I’m just like ‘Alright; there’s only room for one person to be breaking the rules here.”

BTW, Anna is not related to Craig Shoemaker, who grew up in Mt. Airy, Chestnut Hill and Flourtown and is now a successful TV producer in Los Angeles. For more information on the Firefly Music Festival, visit You can check out Anna’s music on her website,