‘When I Look In Your Eyes’: Diana Krall’s Breakthrough Album

Long consigned to pop music’s margins since its 1930s and 40s heyday, jazz enjoyed a surprising renaissance in 2000 when a 35-year-old Canadian female pianist and singer named Diana Krall scooped the Grammy Award for Best Jazz Vocal Performance. The album, recorded a year earlier, also won the Grammy for Best Engineered Album – Non-Classical, awarded to the esteemed veteran audio engineer Al Schmitt. Thrust into the media spotlight by its Grammy successes, When I Look In Your Eyes quickly brought Diana Krall mainstream recognition, transforming her into a bonafide star.

When I Look In Your Eyes was Krall’s debut for Verve Records, the revered jazz label founded by music impresario Norman Granz in 1956 as a vehicle to promote singer Ella Fitzgerald. It was also Krall’s fourth consecutive album working with noted jazz producer Tommy LiPuma and his trusty longtime sidekick, the late Al Schmitt, who saw Krall mature and blossom as her career progressed. “She just got better every time I worked with her,” recalled the engineer to this writer in 2017. “It was wonderful to watch. Every time she was in the studio, she learned something.”

Listen to Diana Krall’s When I Look In Your Eyes now.

Describing her two elder studio mentors as “a great team,” Krall confessed she discovered a kindred spirit in her producer, LiPuma, who nurtured and inspired her. “We’re like married, as far as a musical relationship goes,” she joked in 2001. “He’s like another artist: He’s so into the music and that’s his first and foremost priority.”

LiPuma surrounded Krall with a cadre of top-notch musicians for the session, including a core rhythm section comprising guitarist Russell Malone, bassist John Clayton, and drummer Jeff Hamilton. He also brought on board the veteran composer/arranger Johnny Mandel on seven cuts as a co-producer, arranger, and conductor.

The album mostly explored The Great American Songbook, a huge repository of material mainly written in the 1920s, 30s, and 40s. Irving Berlin’s evergreen “Let’s Face The Music And Dance,” was transformed into a smoulderingly sensuous bossa nova, where Krall’s sultry voice and delicate piano were enhanced by Mandel’s finely nuanced orchestration. A similar lush late-night Brazilian treatment, complete with gentle harp cascades, was given to Krall’s intimate remake of Cole Porter’s “I’ve Got You Under My Skin,” a track indelibly associated with Frank Sinatra. Krall, however, made it her own, infusing it with a sense of deep intimacy and languorous longing.

Certainly, Krall excelled on the album’s lush slower numbers, which revealed her affinity for storytelling ballads and recast her as a torch singer par excellence. But she also showed she could swing with her renderings of “I Can’t Give You Anything But Love,” a duo with guitarist Russell Malone, and “Devil May Care,” a drumless trio number, which was propelled by an infectious, toe-tapping joie de vivre. Showing her repertoire wasn’t confined to The Great American Songbook, she included a playful reading of singer/songwriter Michael Franks’ 1976 tune, “Popsicle Toes.”

In addition to peaking at No. 56 on The Billboard 200, When I Look In Your Eyes spent 32 weeks at the summit of the US Jazz Albums chart, eventually racking up quintuple-platinum sales figures. The album also did tremendously well overseas, particularly in the UK and France, bringing Krall international renown.

Her reputation enhanced by her Grammy triumph, Krall undertook a 20-date US tour in August 2000 with legendary singer Tony Bennett, later appearing on his 2001 duets album, Playin’ With My Friends: Bennett Sings The Blues. At the time, Bennett described Krall as a jazz great in the making. “She’s a natural,” he enthused. “She sings and plays beautiful piano. The minute she starts performing she acquires permanent fans.”

Although her next album, 2001’s The Look Of Love was even bigger commercially and would see Krall expand her audience further, When I Look In Your Eyes was the all-important breakthrough album that put the Canadian chanteuse on the radar of mainstream music buyers and crowned her a jazz queen for the noughties.

Listen to Diana Krall’s When I Look In Your Eyes now.

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