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Best Diana Krall Songs: 20 Jazz Essentials

An introduction to a song interpreter and songwriter obsessed with craft.

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Diana Krall
Diana Krall - Photo: Don Arnold/WireImage

Back in the mid 20th century, the jazz world boasted an abundance of superstars whose names were familiar even to those who had no interest in the music; legendary figures like Louis Armstrong, Count Basie, Ella Fitzgerald, and Nat King Cole. Those days are long gone, of course, but just when the idea of seeing a jazz superstar again seemed an absurdly fanciful notion, along came Diana Krall.

A Canadian from British Columbia, she arrived on the music scene in the early 1990s during a time when grunge, Britpop, and techno were dominating both the airwaves and pop charts. It couldn’t have been a worse period for a fledgling jazz artist whose repertoire mostly consisted of jazz standards. But Krall succeeded in finding an audience and, by the end of the decade, not only had a handful of Grammy nominations to her name but two platinum-selling albums. Against the odds, Diana Krall had helped bring jazz back on to the radar of the mainstream public.

Check out the best Diana Krall songs on Apple Music or Spotify.

Krall’s career reached another level with her sixth album, 2001’s The Look Of Love, which focused more on her singing rather than piano playing, framing her honey-toned contralto voice with opulent orchestral backdrops on a series of ballads and bossa novas. The album quickly went multi-platinum around the world, transforming Krall into the rarest of rarities; a bonafide 21st-century jazz superstar. In the album’s wake came a succession of accomplished albums and a couple of in-concert DVDs that consolidated her fame. And, in a bid to show some versatility, Krall wasn’t averse to taking creative risks; she abandoned her core repertoire, the Great American Songbook, on the pop-tinged albums The Girl In The Other Room (2004) and Wallflower (2015).

What follows are 20 songs that represent Diana Krall at her best, among them finger-clicking swingers, beautiful ballads, and some stellar collaborations. All attest to the exceptional nature of Krall’s talents.

Early years

Born in 1964 in Nanaimo, a city on Canada’s Vancouver Island, Diana Krall grew up in a family where both playing and listening to music were valued pastimes. “I was given piano lessons and lucky to be raised in a very musical environment,” she revealed to Blues & Soul magazine in 2001. “My dad’s a record collector and my grandparents were very musical so it’s a very natural thing for us to hear and play music, especially jazz.”

Krall’s love of jazz continued to blossom in high school, where she played piano in a jazz band; and by the age of 15, she was already performing professionally in local venues. Her determination to become a jazz musician was fueled after she witnessed a concert by Canada’s most famous jazz pianist in 1980: “I went to see Oscar Peterson when I was 16 years old, which made a huge impact on me,” she recalled in 2001.

Serious about making it as a jazz musician, Krall practiced and performed incessantly and won a scholarship at Boston’s prestigious Berklee School of Music; but it was meeting drummer Jeff Hamilton of the group LA Four at a music camp that proved a significant development in her musical life. “That was my big break,” Krall told Blues & Soul. “Jeff encouraged me to come to Los Angeles where I studied with (singer/pianist) Jimmy Rowles and (bassist) Ray Brown.”

Diana Krall’s swing songs

Mentored by Rowles and Brown, Diana Krall blossomed into an assured performer and in 1992 released her first album Stepping Out on the Canadian indie label, Justin Time. With its mixture of piano-driven swingers – which included her sassy reading of Nat King Cole’s 1943 hit, “Straighten Up And Fly Right” – and luxurious ballads, all taken from the jazz standard repertoire, it proved an impressive debut from the 28-year-old. She also received a glowing endorsement from her mentor Ray Brown who wrote of his protégé in the liner notes: “I find that there is a lot of soul in this lady.”

Stepping Out put Krall on the radar of the major label GRP and into the orbit of Tommy LiPuma, a veteran producer, whose credits ranged from Miles Davis to George Benson. He helmed her debut for the label, 1994’s Only Trust Your Heart, which opened with a cover of Louis Jordan’s “Is You Is Or Isn’t You Ain’t My Baby,” transformed into a succulent slice of swinging soul jazz enlivened by Stanley Turrentine’s gruff tenor saxophone asides.

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As Krall’s recording career progressed, her albums became more ballad-oriented but every so often, she showed that at heart, she was still a committed swinger; as evidenced by her vibrant big band reading of the Sinatra classic, “Come Dance With Me,” one of the key cuts from the album From This Moment On, which she recorded with the Clayton/Hamilton Orchestra in 2006.

In concert, Krall refused to dilute the jazz content of her music, and often served up tunes that showcased her piano skills; like the rip-roaring version of the Peggy Lee classic “I Love Being Here With You,” which opened her 2002 album Live In Paris.

The ballads

Diana Krall’s creamy contralto voice, with its dark, velvety texture and richly expressive sonorities, is well-suited to intimate ballads. Producer Tommy LiPuma exploited this talent on several collections of slower songs, which undoubtedly helped Krall become a global phenomenon as the late 1990s moved into the 2000s.

On the bluesy Dave Frishberg tune “Peel Me A Grape,” taken from her 1997 album Love Scenes, Krall showed her skill at working slower material by using a Peggy Lee-style earthiness, where she convincingly morphed into a capricious and demanding temptress.

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Slower songs on later albums were less playful and more nuanced in nature; like the non-album single “Why Should I Care,” which framed Krall’s luscious voice with soft, billowing clouds of luxurious strings. (The song was co-written by the legendary film actor/director Clint Eastwood and was heard during the closing credits of his 1999 movie, True Crime).

Recorded the same year was the slower, Leslie Bricusse-written “When I Look In Your Eyes” – the title track of Krall’s fifth album – which emphasized the aching quality in the singer’s voice; a paean of desire where Krall receives exquisite support from Russell Malone’s guitar filigrees and Johnny Mandel’s sublime orchestral touches.

Another superior ballad performance in Krall’s repertoire is the smoldering torch song “Guess I’ll Hang Out My Teas To Dry,” a melancholy ode written by Sammy Cahn and Jule Styne that has been recorded by everyone from Sinatra to Linda Ronstadt.

The Bossa Novas

Diana Krall’s affinity for the subtle sensuousness of Brazilian bossa nova rhythms first came to light on the When I Look In Your Eyes album; with the help of veteran arranger Johnny Mandel, she transformed two jazz standards from the Great American Songbook – Irving Berlin’s “Let’s Face The Music And Dance” and Cole Porter’s “I’ve Got You Under My Skin” – and slowed them down into lush tone poems underpinned by soft Latin syncopations and infused with a tender eroticism.

Krall went full Brazilian on her next album, 2001’s multi-platinum The Look Of Love; its title track was a gorgeous reconfiguration of Burt Bacharach and Hal David’s Casino Royale tune first waxed by Dusty Springfield in 1967. The arrangement was by the late German arranger, Claus Ogerman, whose resume ranged from Frank Sinatra to bossa nova architects João Gilberto and Antonio Carlos Jobim. He was coaxed out of retirement to write sumptuous charts that draped Krall’s voice with luxurious swathes of soft strings and mellow woodwind.

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Other bossa nova-styled gems from The Look Of Love included a revamp of George Gershwin’s “S’Wonderful” – which echoed Ogerman’s arrangement of the same song for João Gilberto’s Amoroso album in 1977 – and a truly spectacular take on “Dancing In The Dark,” a standard previously recorded by Frank Sinatra and Tony Bennett.

Diana Krall’s pop songs

While there may have been some who bemoaned the diminishing jazz content of some of her records in the 2000s, Diana Krall’s experiments with pop songs reflected her desire to take creative risks. 2004’s The Girl In The Other Room was mostly self-written and moved away from the jazz standard repertoire. It also contained Krall’s take on “Black Crow,” a song written by another of the singer’s idols; fellow Canadian Joni Mitchell, whose influence was almost palpable on the songs “Narrow Daylight” and “Departure Bay,” two storytelling confessionals Krall co-wrote with her new husband, British singer/songwriter Elvis Costello. (They married in 2003).

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Krall also put jazz and her piano playing on the back burner with her 2015 album Wallflower, where she offered mostly slick David Foster-produced interpretations of classic 60s and 70s pop and rock songs; they included her impassioned version of The Eagles’ anthemic country-rock ballad “Desperado.”

The duets and collaborations

One of the first people that Diana Krall duetted with on record was Tony Bennett, when she appeared opposite the veteran crooner on his 2001 album Playing With My Friends: Bennett Sings The Blues. The two reunited for a full LP in 2018, Love Is Here To Stay, which included a delightfully playful interpretation of George and Ira Gershwin’s “Fascinating Rhythm.”

Other noteworthy collaborations in Krall’s catalog include a tender reading of fellow Canadian Gordon Lightfoot’s 1970 breakup song “If You Could Read My Mind,” sung as duet with her compatriot, singer/songwriter Sarah McLachlan and a striking stylistic departure in the shape of Bob Dylan’s waltz-time frontier-style ballad, “Wallflower,” featuring the distinctive fretwork of American guitarist Blake Mills. (Both tracks appeared on Krall’s 2015 album, Wallflower).

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Although Diana Krall has been typecast as a jazz balladeer – something that has sometimes been a source of frustration to her – the 20 songs we’ve selected reveal that she’s far more versatile than one might think. While jazz is where she first made her name, over time she has revealed herself to be a risk-taking musician with bold expeditions into other genres.

Think we missed one of the best Diana Krall songs? Let us know in the comments below.

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