Born in Nanaimo, British Columbia (not far from Vancouver), Diana Krall grew up in the western part of Canada and began studying the piano when she was four years old. By the time she was 15, she was playing jazz in a local restaurant/bar. One person who encouraged her interest in music was her father, a stride pianist with a vast knowledge of such Twenties and Thirties keyboard masters as Fats Waller, James P. Johnson, and Earl Hines. "I think Dad had every recording Fats Waller ever made," she says, "and I tried to learn as many as I could."

Krall was still a teenager when she was awarded a scholarship to the prestigious Berklee College of Music in Boston. After two years in Boston, she moved to Los Angeles, where she met her first jazz heavyweights, including John Clayton, pianist/singer Jimmy Rowles, and Ray Brown, the legendary bassist who served as her musical mentor (and played on Only Trust Your Heart). Krall had lived in Los Angeles for three years when she moved to Toronto, and it was a Canadian label that gave her a chance to record for the first time. In 1993, the Montreal-based Justin Time Records released her debut album, Stepping Out. In 1994, she signed with GRP and recorded Only Trust Your Heart, which featured Brown on bass and Stanley Turrentine on tenor saxophone and marked the beginning of her association with Tommy LiPuma (who has worked with everyone from Barbra Streisand to George Benson).