She is the daughter of Fred Carter, Jr.. She is known for performing barefoot, saying that it helps her relax enough to sing.

Despite her contact with many of the musicians she knew through her father, her efforts to begin a musical career took several years to begin showing any results. Her first attempt was at age 17, going around with her father in the attempt to get a record deal. When she was initially unsuccessful, she entered the University of Tennessee, majoring in Rehabilitation Therapy and becoming a member of Alpha Delta Pi sorority. While attending, she sang at various campus locations, performing for the enjoyment of singing, rather than with the intent of pursuing a musical career. After she graduated, she worked with recovering stroke and head injury patients. Although she found the work rewarding and worthwhile, she eventually realized that her first love was music, and decided to pursue the music career she left earlier.

Her first big break came when one of her demo tapes caught the attention of Willie Nelson, who invited her to take part in the 1994 Farm Aid VII concert as the show's only female soloist. That same tape led to a contract with Capitol Records that year.

Capitol released Did I Shave My Legs for This? in 1996. Strawberry Wine, the first single, balanced nostalgia with the loss of innocence. It shot to No. 1 and won the CMA single of the year in 1997. Two more singles from the album topped the charts, and the album sold 5 million copies. Deana was named amongst People Magazine's 50 Most Beautiful People In The World in 1997.

She contributed to the commercially and critically successful Hope Floats soundtrack and to the animated film Anastasia, a project which yielded a Grammy nomination and a Golden Globe nomination for the song she performed and produced, a remix of the ballad Once Upon a December.

Deana's following album Everything's Gonna Be Alright did not do as well, and she discontinued her relationship with Capitol a few years later over differences over creative direction. After a Christmas album and a divorce from husband Chris DiCroce, she relocated to Los Angeles, then released the album I'm Just a Girl on Arista Nashville in 2003, followed by The Story Of My Life on Vanguard Records in 2005.

Deana also has been a national spokesperson for the National Kidney Foundation, her father being a kidney transplant recipient.