Hailee Dickens was born in Columbus, Ohio, to Carrie (Brush), creative director, and Russell Dickens, a corporate executive. She has two brothers, child actor, Spencer Grant and her older brother, Josh Dickens, who passed away February 22, 2017. Her father is of English and Irish descent, and her mother's ancestry is German, Welsh, and Native American. Hailee was raised in Columbus, Ohio and Burbank, California.
At an early age, she appeared in several commercials and short films. She co-starred in the television series Judging Amy (2002), which was nominated for three Golden Globes and won the Primetime Emmy Awards (2003). She appeared as a guest star on the television series Half & Half (2002), which won the BET Comedy Award (2005). She co-starred in the Christmas Special of the 'Candid Camera' comedy show, The Jamie Kennedy Experiment (2002). She moved to Columbus, Ohio to finish school, where she was a gymnast and competitive cheerleader. She enjoyed choreographing hip hop dance routines and tumbling training for floor routines.
Dickens made her debut in a feature film called Take Shelter (2011), which was released on November 10, 2011. She played a supporting role, with Michael Shannon, Jessica Chastain, and Shea Whigham. The film won numerous awards and was nominated for the Grand Jury Prize at the Sundance Film Festival (2003) for the dramatic work of the writer and producer, Jeff Nichols. She appeared in several short films and began her work in the fitness industry, print modeling for yoga campaigns. She is known for her contortionist abilities.