Diana Krall is one of the most celebrated jazz pianists and vocalists of her generation, a rare artist who bridges the worlds of traditional jazz, bossa nova, and sophisticated pop with effortless grace. Her catalog is vast and rich, and narrowing it down to the 20 best songs of Diana Krall feels both thrilling and a little heartbreaking — there are just so many standout moments. But these tracks represent the full arc of her artistry, from the smoky intimacy of her early recordings to the lush orchestral arrangements of her later work. Whether you’re a longtime devotee or just discovering her through a late-night recommendation, this list is your gateway into one of music’s most elegant bodies of work. Put on your best pair of headphones and settle in — this is Diana Krall at her finest.
The Look of Love
Few songs suit Diana Krall’s voice like this Burt Bacharach and Hal David classic. Originally written for the 1967 film Casino Royale and famously recorded by Dusty Springfield, Krall’s 2001 version — the title track of her Grammy-winning album — is something else entirely. Her piano introduction alone sets a mood so intimate you feel like you’ve stumbled into a late-night supper club by accident. The arrangement is sparse and knowing, leaving enormous space between notes, and her voice is almost conversational — unhurried, warm, and impossibly cool. This track established Krall as not just a jazz interpreter but a genuine emotional storyteller.
Just the Way You Are
When Diana Krall tackled Billy Joel’s 1977 soft-rock masterpiece for The Guru soundtrack, many wondered how it would translate. The answer: magnificently. She strips away all the pop sheen and recasts it as a late-night jazz ballad, with her piano doing most of the emotional heavy lifting. Her phrasing is tender but never sentimental — she inhabits the lyric with the kind of lived-in conviction that only comes from genuine musical understanding. It’s a reminder that truly great songs transcend genre when placed in the right hands.
Let’s Fall in Love
From the Grammy-winning album When I Look in Your Eyes, this is Krall at her most playful and swinging. The Harold Arlen tune gets a brisk, bouncy treatment here, with her rhythm section driving things forward while her piano lines dart in and out like a dancer. Her voice is light and bright, flirtatious even, and the whole thing feels spontaneous even though every note is perfectly placed. This is the track you play for someone who insists jazz is too serious — it’ll change their mind in about 90 seconds.
Temptation
The Girl in the Other Room album marked a turning point for Krall — co-written largely with her husband Elvis Costello, it was a more personal and sometimes darker record. This track is one of its most compelling moments, a slow-burning performance that showcases her lower vocal register and her gift for building dramatic tension. The production, handled by T Bone Burnett, is rich and slightly cinematic, with the arrangement breathing like a living thing. If you want to hear Krall in a more brooding mode than her jazz standards work, this is the first stop.
Peel Me a Grape
Dave Frishberg’s witty 1962 song is one of the great comic jazz numbers, and Krall’s version on Love Scenes is an absolute treat. She plays it with a knowing smirk in her voice — arch, a little imperious, utterly charming. The intimate duo setting with bassist Christian McBride makes the whole thing feel like a private performance. It’s one of those tracks that reminds you how much fun jazz can be when the material is this smart and the performer is this confident. Pairs brilliantly on shuffle with any Ella Fitzgerald sides, if you’re building a playlist over at songs.
Cry Me a River
This is the 1955 Arthur Hamilton original, a song of righteous romantic fury, and Diana Krall delivers it with devastating precision on The Look of Love. Her piano introduction is bluesy and deliberate, setting a mood of cold-eyed recrimination before she even opens her mouth. When the voice comes in, it’s controlled and chilling — she makes the narrator’s contempt feel entirely earned. Producer Tommy LiPuma frames the whole thing in perfect sonic balance, and the result is one of the definitive recordings of a song that has been covered hundreds of times.
Love Is Here to Stay
For her 2018 album of the same name, Krall partnered with the Clayton-Hamilton Jazz Orchestra to interpret the Gershwin brothers’ catalog, and the results were sumptuous. This track — George and Ira’s final collaboration before George Gershwin’s death in 1937 — gets a full orchestral treatment that feels both celebratory and bittersweet. Krall’s voice floats above the big band arrangement with the ease of a seasoned bandleader, and her piano playing during the solos is precise and lyrical. It’s a masterclass in how to honor a classic without being enslaved by it.
Autumn in New York
From This Dream of You, a 2020 album recorded largely from her archive of sessions with producer Tommy LiPuma before his death, this performance is absolutely heartbreaking in the best possible way. Vernon Duke’s 1934 standard has been covered by virtually everyone, but Krall finds something private and elegiac in it. The arrangement is chamber-like — her piano, a gentle rhythm section, occasional strings — and her voice carries a weight that goes beyond mere technique. Listening on headphones in the actual autumn is a near-religious experience.
Alone Again
The Wallflower album was Krall’s deep dive into pop songbook territory, and her cover of Gilbert O’Sullivan’s 1972 hit is one of its most affecting moments. Where the original is melancholic in a somewhat theatrical, baroque-pop way, Krall’s reading is quieter and more interior — she sounds genuinely reflective, not performative. The production by David Foster frames her voice beautifully without over-ornamenting it. It’s the kind of cover that makes you think about the original differently — and that’s the highest possible praise.
Night and Day
Cole Porter’s 1932 classic is one of the most-recorded songs in the entire jazz canon, and Krall’s take holds its own in very distinguished company. Her approach is confident and unhurried — she doesn’t try to reinvent the song, but rather inhabits it with complete authority. The rhythmic feel sits somewhere between a slow swing and a ballad, giving the performance an elastic quality that keeps you off-balance in the most pleasurable way. Her piano comping throughout is understated and intelligent, the mark of a musician who knows when to lead and when to support.
I’ve Got You Under My Skin
Another Porter gem from When I Look in Your Eyes, this one shows Krall at her most unabashedly romantic. The arrangement builds from a gentle piano-and-bass introduction into a fuller ensemble sound without ever losing its intimate feel — no small feat. Her voice on the climactic sections, where the lyric really twists the knife emotionally, is controlled and gorgeous, holding back just enough to make the feeling land harder. Few jazz singers can balance technical precision with genuine feeling this seamlessly.
Narrow Daylight
One of the original compositions from The Girl in the Other Room — co-written with Elvis Costello — this is among Krall’s most personal recordings. The lyric is impressionistic and slightly opaque, the way the best poetry is, and Krall sings it with a rawness that her jazz standards work rarely demands. T Bone Burnett’s production gives it a rootsy, slightly cinematic texture, and the guitar work in particular adds an earthy dimension to her usually piano-centric sound world. It’s an underrated gem in her catalog.
California Dreamin’
This is a genuinely surprising choice that pays off brilliantly on Wallflower. The Mamas and The Papas’ 1965 classic is one of the most iconic songs of the folk-rock era, built on lush vocal harmonies and a very specific Californian longing. Krall strips all of that away and replaces it with a measured, almost hymn-like solemnity. Her piano anchors everything, her voice is spare and searching, and the whole arrangement suggests genuine yearning rather than nostalgia. It’s proof that she can make virtually any song her own.
Why Should I Care?
Written by Clint Eastwood and Carol Bayer Sager for the 1999 film True Crime, this song found a perfect interpreter in Diana Krall on When I Look in Your Eyes. The lyric is philosophical and world-weary without being bitter, asking genuine questions about love and indifference, and Krall delivers it with exactly the right amount of detachment. Her piano arrangement adds modal jazz touches that give the song an almost Miles Davis-adjacent feeling at moments. It’s one of the more compositionally interesting tracks in her catalog.
S’Wonderful
From The Look of Love, this George and Ira Gershwin tune gets a delightful, uptempo treatment that showcases the sheer joy in Krall’s jazz playing. The band swings hard, her piano lines are quick and witty, and her voice has a brightness and playfulness that’s genuinely infectious. This kind of recording demonstrates why producers kept bringing Krall back to the classic songbook — she doesn’t just interpret these songs, she illuminates them. If this doesn’t make you want to immediately build a jazz playlist with the help of resources at songs on GlobalMusicVibe, nothing will.
A Case of You
Covering Joni Mitchell’s deeply personal 1971 song from Blue is an act of considerable artistic courage, but Krall pulls it off with grace and intelligence. She doesn’t try to replicate Mitchell’s ethereal folk-pop delivery; instead, she places it in a jazz context with a flowing piano accompaniment that lets the lyric breathe and the imagery unfold. The result is something new but respectful — a reading that honors the original while finding new emotional dimensions in the words. It may be the single best cover in her discography.
Desperado
Another Wallflower triumph, Krall’s reading of the Eagles’ 1973 lament for emotional self-imprisonment is strikingly intimate. She slows it down even further than the original, letting each word settle into the silence around it. Her piano introduction is beautifully spare, and when her voice enters it feels like a quiet intervention rather than a performance — she’s addressing the song’s subject directly, gently, without judgment. David Foster’s production keeps everything clean and uncluttered, letting the song’s inherent sadness speak for itself. For best results, listen through quality earbuds in a quiet room — the details reward close listening.
So Nice
From Quiet Nights, her 2009 bossa nova-themed album produced by Tommy LiPuma and Claus Ogerman, this track (the English version of Marcos Valle’s Samba de Verao) is sun-drenched and gorgeous. The orchestral arrangement by Ogerman is silky and sophisticated, and Krall’s vocal is pure pleasure — warm, rhythmically supple, and completely at home in the Brazilian idiom. The album was a passion project for Krall, and you can hear it in how deeply she inhabits the material. This is perfect warm-weather listening, best experienced with those headphones on and your eyes closed.
Frim Fram Sauce
From her debut album Stepping Out, this track showcases how fully formed Krall’s jazz voice already was in the early nineties. It’s a playful, nonsense-lyric novelty number — popularized by Nat King Cole — and Krall sings it with the kind of loose, swinging joy that defines classic trio jazz. Her piano playing here is notably bebop-influenced, and the interplay with her rhythm section is exceptional. Hearing this alongside her later, more polished work is a reminder that her gift was always prodigious; the production values just caught up over time.
How Deep Is the Ocean
We close with this profound Irving Berlin ballad from Love Scenes, a track that demonstrates everything that makes Diana Krall exceptional. The song — written in 1932 as a series of rhetorical questions quantifying love — gets a slow, almost somnolent treatment that gives every phrase room to resonate. Krall’s piano playing is at its most lyrical, and her voice is soft but totally controlled, drawing out the phrases with a patience that feels almost meditative. It’s the kind of performance that makes you sit quietly for a moment after it ends. A perfect closing statement.
Frequently Asked Questions
What is Diana Krall’s most famous song?
Diana Krall is perhaps most recognized for her version of The Look of Love, the title track from her 2001 album. It became one of the signature recordings of her career, earned her significant mainstream attention, and is regularly cited in critical discussions of her best work. That said, long-time fans often point to recordings like Cry Me a River or A Case of You as equally definitive.
What genre does Diana Krall sing?
Diana Krall works primarily in jazz, specifically the vocal jazz and jazz standards tradition associated with the Great American Songbook. However, her catalog also embraces bossa nova on Quiet Nights, blues-inflected pop on The Girl in the Other Room, and contemporary pop songbook covers on Wallflower. She resists easy categorization, which is part of what makes her catalog so rewarding to explore.
Has Diana Krall won a Grammy Award?
Yes, Diana Krall has won multiple Grammy Awards over the course of her career. She took home the Grammy for Best Jazz Vocal Album multiple times, including for When I Look in Your Eyes in 2000 and The Look of Love in 2002. She has also received numerous additional nominations across various categories.
Who produced most of Diana Krall’s albums?
The late Tommy LiPuma was Diana Krall’s most important long-term collaborator and producer, responsible for much of her classic output from the mid-1990s through the 2000s, including Love Scenes, When I Look in Your Eyes, The Look of Love, and Quiet Nights. His ear for arrangement and his ability to frame her voice beautifully was central to her sound. She has also worked with T Bone Burnett on The Girl in the Other Room and David Foster on Wallflower.
Is Diana Krall primarily a singer or a pianist?
Diana Krall is genuinely both — a highly accomplished jazz pianist who also sings, rather than a singer who happens to play piano. She studied under master jazz pianists early in her career and has always led her own piano-centric trios. This dual identity sets her apart from most jazz vocalists and gives her recordings a unique quality: the piano accompaniments are never mere support, they are full musical conversations.
What is Diana Krall’s best album for new listeners?
When I Look in Your Eyes from 1999 or The Look of Love from 2001 are both excellent entry points — they’re accessible, beautifully produced, and showcase her strengths as both pianist and vocalist across a range of tempos and moods. For something more adventurous, The Girl in the Other Room from 2004 shows a different, more personal side of her artistry.