I’m looking forward to a production of Into the Woods. I’m a teenager in high school and the eldest person auditioning. I don’t know much about singing. My range is G5-A3. Apparently my voice is very sweet sounding and whenever I sing I sound sad.
My main question is knowing which role to go for and maybe recommendations for the song for the role. I’m sorry if this is too much to ask. Also if you have any additional questions please ask.
That's exciting! Based on your range and the description you've given, Little Red, Jack's Mother, and Cindy's Step Family (Step mother, Florinda, and Lucinda) are all within your range (Granny is also possible, but since she only really sings in an ensemble capacity, we'll leave her out in terms of audition material). Sweet and sad may also get you considered for Cinderella's Mother (a little high for you as it goes up to an A5, but don't count yourself out. A whole step is a totally possible stretch to make at that place in the voice. And if you can stretch up to that, Rapunzel is also possible and fitting for your tone quality).
For Little Red: The Glamorous Life from A Little Night Music (the film version--one of the few good things about that film adaptation. Audra McDonald has a beautiful rendition you can reference); Everlasting from Tuck Everlasting; or, if you can find a solo cut, I Know It's Today from Shrek (this cut of Morning Person would also work well)
For Jack's Mother and/or Cinderella's Stepmother: Wait from Sweeney Todd or Sensitivity from Once Upon a Mattress
Cinderella's Mother/Rapunzel: Come to my Garden from the Secret Garden or One More Kiss from Follies.
Florinda/Lucinda: Stepsister's Lament from the R&H Cinderella (very on the nose as a choice, but fun) or (perhaps a little young and bratty, but so very step sisters) I Want it Now from Willy Wonka and the Chocolate Factory.
As for which one to go for, that's something I can't really advise on without knowing how tall you are compared to the other kids auditioning, how old you read next to them, actually hearing your voice, etc. Go for the role that most speaks to you.