[2][3] Caldwell was born in Washington, D.C., and ran away to New York several times through her teenage years to see shows on Broadway and figure "things out".
[6] In 1998 she secured her longest lasting screen role, that of Asia Franklin in both seasons of the TV series Little Men based on Louisa May Alcott's sequel to Little Women.
[11][12][13] For many decades Caldwell would not tell people that she was born a male and lived with the fear that this news could devastate her and her career: "You wake up afraid.
"[14] After writing and performing her autobiographical musical show “The Guide to Being Fabulous After You’ve Skinned Your Knee,” at Berkeley Street Theater in Toronto in 2010,[15] Caldwell entered a period of depression concerned that she needed to disclose even more of the truth of her life.
Variety's Marilyn Stasio called Caldwell a "black transgender woman of immense poise, beauty and—pardon me, I can’t help myself—charm," and New York magazine's Sara Holdren praised her as "classy and charismatic.