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.
In early 1995 she released her debut album, Did I Shave My Legs for This?, in the UK on Patriot Records. However, the label folded shortly after the album's release. In 1996, Carter released her debut country single, "Strawberry Wine," which reached No. 1 on the U.S. Billboard Hot Country Singles & Tracks. Did I Shave My Legs for This? was released in North America (keeping only three of the original tracks) to great success. The album debuted at No. 2 on the U.S. Top Country Albums chart and sold well over five million copies, and produced two further No. 1 hits in "We Danced Anyway" and "How Do I Get There."
Carter was featured on the Soundtrack to the 1997 animated movie Anastasia, for her version of "Once Upon a December." The track was made into a music video and received rotation on CMT at the time "How Do I Get There" was charting as a radio single (since the single had no music video).
In September 1998, Carter released her sixth single, "Absence of the Heart," as the lead-off single to her second album, Everything's Gonna Be Alright, which was released on October 20, 1998. The album peaked at No. 6 and sold just enough to receive a Gold certification, far less than the sales of her debut album. The album produced a Top 20 in its lead single and three further singles, two of which were minor Top 40 hits ("You Still Shake Me" and "Angels Working Overtime").
After releasing her third studio album, Father Christmas, on Rounder Records in November 2001, and a divorce from husband Chris DiCroce, she relocated to Los Angeles.
In 2002, Carter signed with Arista Nashville and released her first single in three years. "There's No Limit," which became her sixth Top 20 hit with a peak of No. 14 in early 2003, served as the lead-off single to her fourth studio album, I'm Just a Girl, which was released on March 18, 2003. The title-track was released as the album's second single, and was a minor Top 40 hit. No further singles were released from the album, and Carter once again parted ways with her record label.
In 2004, Carter signed with independent record label Vanguard Records. She released the song "(Bleep) Texas" in March 2005, but it failed to chart and was shortly replaced with "One Day at a Time," which served as the lead single to her fifth studio album, The Story of My Life. It only remained on the chart for five weeks and peaked at No. 55. The Story of My Life peaked at No. 26 on the U.S. Country Albums chart, and all further singles ("The Girl You Left Me For," "Sunny Day," and "In a Heartbeat") failed to chart. Despite having less success, Carter had more artistic freedom with this album and was able to write (or co-write) and produce all 11 tracks.
Carter's sixth studio album, The Chain, was released on October 9, 2007. The Chain was a cover album, that she recorded as a tribute to her father (who performed guitar on many of the original versions of the covers found on the album). Many of the tracks also featured the original artists as duet partners, such as Dolly Parton (on "Love Is Like a Butterfly") and Willie Nelson (on "On the Road Again"). The album was unsuccessful; it debuted and peaked at No. 60, and its only single (the duet version of "On the Road Again" with Nelson) failed to chart.
Carter was ranked No. 81 on the 100 Greatest Women (of Country Music) by Country Universe in 2008.
Carter dated music video Director Chris Hicky and had a son during their relationship; Gray Hayes Hicky was born in September 2004. On October 3, 2009, Carter married boyfriend Brandon Malone in Malibu. In November 2012, Carter filed for legal separation from her husband, Brandon Malone citing irreconcilable differences.
In 2010, Kenny Chesney covered "You and Tequila," a song co-written by Carter with Matraca Berg for the album I'm Just a Girl, and included it on his album Hemingway's Whiskey. Chesney's version was later released as the album's fourth single in May 2011 and features guest vocals from Grace Potter. It peaked at number 3 in September 2011, and was nominated for Song of the Year at the 2011 CMA Awards.
Deana Carter's third studio and holiday album, Father Christmas, was re-released on December 13, 2011 via Adam Ant Records, ten years after its initial release.
In 2013, Carter formed her own record label, Little Nugget Records. Southern Way of Life, Carter's seventh studio album, released on December 2, 2013. In 2013, Carter re-released Father Christmas with her own record label, Little Nugget Records