Anna is no stranger to show business, she appeared in her first magazine advertisements when she was only ten months old. She has also appeared in industrial films, TV commercials, and in two productions of "Annie", as well as an on stage performance in "Fiddler on the Roof" and "The Music Man".
She made her film debut as a hypochondriac tomboy in "My Girl (1991)" opposite Macaulay Culkin. Her role in this movie led to the sequel "My Girl 2 (1994)" where she travels to Los Angeles to discover her dead mother. Her next movie, "Trading Mom (1994)" was again about mothers where she co-starred with Sissy Spacek, who played the mother that was replaced by her evil clone. Anna played a neglected tom-boy and shared the screen with Christina Ricci in "Gold Diggers: The Secret of Bear Mountain (1995)". The two become friends and share a number of adventurous scrapes with the spoiled city girl played by Ricci. She played two more roles in 1997: "A Childs Wish" and "Miracle in the Woods". 1998 brought her a part in the tv-series "Cupid", where she played a homeless girl called Jill, and a part in "Early Edition".