Hey Jelly! I pondered my orb and it told me that you were asking for my top 5 singers, so here goes:

Tori Amos. She and her music were so important to me in my twenties and early thirties. Essential, really. I literally wouldn't be the same person without her lyrics. It's like her music was made for me. I'm not listening to her as much anymore, but she's still my number one, definitely the best American pop musician and lyricist of her generation (or the 20th century tbh.)

Regina Spektor. (Yes problematic, I know.) I can't cancel her completely. Yet. Because her music was my anchor in my twenties. The way she writes about love ... yeah, she gets me. I get her.

Vanessa Carlton. Yes, you can laugh. She's underrated, though. I bought her debut at a library sale ~ 15 years ago and realized that she's so much more than You Know What. I really relate to her albums, it feels like we went through similar things at the same time. I listen to her a lot.

Joanna Newsom. My princess, my baby girl, I don't understand you but I love you. Colleen is my favorite song of all time, probably.

There's a tie for number 5 because there are so many (Kate Nash, PJ Harvey, India.Arie, Juana Molina, Solange, ......) so I'm gonna go with Sequoyah Murray because his voice is everything and he's criminally underrated. More people need to listen to him, his music is magic.

Thanks for the ask!!!