Miss Chalice is homeless (duh) but she still manages to sleep in relatively nice places. When she can’t con her way into empty hotel rooms she sleeps in churches, libraries, and other places that are unused at night.
Kettle never really adopts Chalice (unfortunately), but she’s over at their house so often she becomes an unofficial part of the family. Kettle is the only adult she trusts to get advice from.
Kettle tried acting as her dad a few times. It didn’t end well.
The cups can’t feel their straws. But they know when it’s being touched, in the same way you know your when hair is being touched.
Their handles are the least sensitive parts of their bodies, which is why it didn’t hurt when Mugman broke his.
Mugman never got the hang of the piano. But he found that a trumpet was somehow easier for him to manage.
When Mugman, Cuphead, and Chalice become young adults they start performing together. Chalice as the singer/dancer, Cuphead at the piano, and Mugman on the trumpet. (Mugman still has stage fright, so he wears glasses so dark he can’t see the audience lol). Their act is very successful, but doesn’t last forever.
Chalice eventually makes it big in the acting industry :)
I also headcannon that Chalice starts thinking about her direction in life. She knows that the afterlife exists, and last time she died she literally went straight to the Devil. She wants to be smarter this time. She goes to church, donates large sums to charity, builds a proper orphanage. She sure hopes it’ll be enough.
Adult Mugman deals with his intimate brushes with death a different way, Casino Cups style.
Cuphead ain’t too worried about it.
I headcannon that Elder Kettle is an old coffee kettle. Does he look like a teapot? No. Therefor he’s full of coffee.
Cuphead has ADHD and more fears than he admits.
Chalice has life-long trust issues.