In 1993, Krall released her first album, Stepping Out, which she recorded with John Clayton and Jeff Hamilton. It caught the attention of producer Tommy LiPuma, who produced her second album, Only Trust Your Heart (1995).

Her third, All for You: A Dedication to the Nat King Cole Trio (1996), was nominated for a Grammy and continued for 70 weeks in the Billboard jazz charts. Love Scenes (1997) quickly became a hit record with the trio of Krall, Russell Malone (guitar) and Christian McBride (bass).

In August 2000, Krall was paired on a 20-city tour with Tony Bennett.

Orchestral arrangements by Johnny Mandel provided the background on When I Look In Your Eyes (1999); more Grammy nominations came along, and she was rewarded as Best Jazz Musician of the Year. The band mix was kept, following arrangements on The Look of Love (2001) created by Claus Ogerman; this record achieved platinum status and reached the top 10 of the Billboard 200. The Look of Love went to number one on the Canadian album charts and went quadruple platinum in that country. The title track from the album, a cover of the Casino Royale standard popularized in the late 1960s by Dusty Springfield and Sergio Mendes, reached number 22 on the adult contemporary chart.

In September 2001, Krall began a world tour. Her concert at the "Paris Olympia" was recorded and released as her first live record. Diana Krall - Live in Paris topped the Billboard jazz charts, went top 20 on the Billboard 200 and went top 5 in Canada. It garnered her second Grammy (Best Vocal Jazz Record) and a Juno Award. The album included covers of Billy Joel's "Just The Way You Are" (a hit on U.S. smooth jazz radio) and Joni Mitchell's "A Case Of You."

After getting married to Elvis Costello, she worked with him as a lyricist, and started to compose her own songs, resulting in the album The Girl in the Other Room. The album, released in April 2004, quickly rose to the Top 5 in the UK and made the Australian top 40 album charts. "Temptation", a cover of the Tom Waits song off his Frank's Wild Years album of 1987, reached number 1 of the World Jazz Charts (based on the US, Germany, France, Japan and China).