What I'm Listening To | My 20s Soundtrack: Female Singer-Songwriters


It all started when I randomly found myself thinking of the song "Ask Me" by Susan Cagle, who I had become a fan of after hearing her play in a subway station back in 2006. Then while I was at Walgreens, a song by Schuyler Fisk came on, who was yet another throwback musician that I used to be obsessed with during 2009. I hadn't heard either of their songs in forever but it got me thinking about all the female singer-songwriters I listened to throughout my twenties and that's how this playlist was born! 


Song are in chronological order by release date:

1. "Breathe" by Michelle Branch

I was torn between this or "Desperately" but in the end, I had to go with this.

2. "Ask Me" by Susan Cagle
These lyrics still give me all the feels. 

3. "Like a Star" by Corinne Bailey Rae
This song brings back so many memories of a crush I had. 

4. "Fidelity" by Regina Spektor
Her sound was unlike anyone else at the time (and still is!) and I immediately fell in love with this song. 

5. "Gravity" by Sara Bareilles
There's a note in this song that gives me chills every time. And it's even better hearing it live!

6. "Near To You" by A Fine Frenzy
Clearly, I was obsessed with very emotional lyrics. 

7. "Silvery Lining" by Rilo Kiley
Super into the vibe of this song then and now.

8. "Say It Again" by Marie Digby
I still remember when her cover of "Umbrella" went viral. I became a huge fan and I still enjoy her first album all these years later plus some of her newer music too. 

9. "I Feel It All" by Feist
The first time I heard of Feist was for an iPod Nano 6th Generation commercial (I feel so old, lol). This song was my favorite of hers though. 

10. "From Where I'm Standing" by Schuyler Fisk
I first heard this song and of Schuyler Fisk in the movie "I'm Reed Fish" and that's how I became a fan. 

11. "Shark in the Water" by VV Brown
This is such a fun song! I immediately want to dance in my chair when I hear it. 

12. "Concrete Wall" by Zee Avi
There is something so soothing about her voice. 

13. "Blue Ribbon Winner" by Schuyler Fisk
I had this song on repeat back in 2011 and it's on repeat again now. 

14. "Irregular Heart" by Schuyler Fisk
Can you tell I'm a fan yet? Basically since I put together this playlist, I've been listening to her second album constantly. 

15. "Live Your Life" by Yuna
The title alone made this a fitting song to end this playlist on!

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What are some of your favorite songs from your 20s?

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with love,

Rachel