Holly Cole is one of those rare artists who makes you fall in love with a song you never thought you needed. The Canadian jazz vocalist and her longtime trio — pianist Aaron Davis and bassist David Piltch — have spent decades reimagining standards, folk songs, pop hits, and torch ballads into something entirely their own. Whether she’s whispering over brushed drums or cutting straight to the bone on a spare piano arrangement, Holly Cole possesses a voice that feels like smoke curling through a winter room.
This list of the 20 best songs of Holly Cole is not just a ranking — it’s a listening journey through one of the most distinctive catalogs in contemporary jazz and cabaret. If you’re serious about exploring music that rewards close, headphone listening, this is where you start.
Calling You
There are songs that stop you cold, and “Calling You” is one of them. Originally written by Bob Telson for the 1987 film Bagdad Café, Holly Cole’s interpretation, recorded for her 1995 album Temptation, strips the track down to its emotional marrow. Her voice here is unhurried, almost conversational, floating above David Piltch’s resonant bass with nothing to hide behind. The production is minimal by design — every breath, every pause is audible — and that intimacy is precisely what makes it devastating. On headphones, especially, you can hear the room, the silence between notes, and the way Cole chooses to let the melody breathe rather than oversell it. It remains the definitive cover of this song.
I Can See Clearly Now
Most people know “I Can See Clearly Now” as a reggae-sunshine anthem from Johnny Nash, but Holly Cole turns it inside out on her 1995 album Temptation. Her arrangement is lounge-dark and deliberate, slowed to a crawl that transforms optimism into something closer to hard-won resolution. Aaron Davis’s piano work here is understated genius — a few chord voicings that reframe the entire emotional register of a song the world thought it already understood. It’s a masterclass in the art of reinterpretation, and it reminds us that the best covers don’t imitate; they reveal. This track has introduced countless listeners to the idea that jazz singers aren’t just interpreters — they’re composers in their own right.
Jersey Girl
Tom Waits wrote “Jersey Girl” in 1980, and Bruce Springsteen later made it a classic-rock staple, but Holly Cole’s version — recorded for her debut album Girl Talk in 1990 — is something else entirely. She sings it with a devotional ache, and the trio’s arrangement favors warmth over bombast. What strikes you is how intimate the lyric becomes when you remove the stadium reverb: this is just a love song, plain and simple, delivered straight to you. Cole has always had a particular affinity for Tom Waits material, and this early recording shows that connection was there from the very beginning of her career. It’s one of the great deep cuts in her catalog.
I Want You
Elvis Costello’s “I Want You” from Blood and Chocolate (1986) is one of the most emotionally intense songs ever written — an obsessive, coiling, devastating examination of longing. Holly Cole recorded it for Temptation, and her version doesn’t defang it. Instead, she channels the song’s relentless hunger through her particular vocal restraint, which somehow makes it more unbearable. The piano arrangement is sparse and deliberate, and Cole’s phrasing is meticulous — she knows exactly where to press and where to pull back. This is one of those tracks best heard alone, late at night, when you’re ready to sit with something uncomfortable. It’s proof that jazz vocal interpretation can handle the full weight of rock songwriting.
Make It Go Away
“Make It Go Away” is one of Holly Cole’s most achingly beautiful performances, a quiet plea that lives in the softest register of her voice. Released on her 1998 album Holly Cole, the song is built around a simple piano-bass foundation that gives her nowhere to hide — and she doesn’t try. The lyric is deceptively simple, about the desire to escape pain, and Cole delivers it with the kind of emotional precision that only comes from a singer fully committed to the story. In the context of an album full of mood and texture, this song stands out for its raw, unadorned vulnerability. It’s the kind of track that finds you on a gray afternoon and doesn’t let go.
Trust in Me
Holly Cole’s take on “Trust in Me” — the jazz standard with roots stretching back to 1934 — is silky and knowing, with a performance that understands every implication of the lyric. Her voice wraps around the melody with a confidence that feels completely natural, and the trio’s accompaniment is perfectly calibrated: present enough to support, restrained enough to let her lead. It’s the kind of jazz performance that feels effortless because of how much craft is behind it. For listeners exploring classic jazz vocal songs and standards, this is an ideal entry point into Holly Cole’s command of the Great American Songbook.
Train Song
Another Tom Waits cover, “Train Song” from Frank’s Wild Years (1987), finds Holly Cole in melancholic, rolling territory. The trio leans into the song’s locomotive imagery through rhythm and repetition, and Cole’s vocal has a weathered, road-worn quality that suits the material perfectly. There’s a bluesy undertow here that distinguishes it from her smoother recordings — this is Holly Cole comfortable in grit. The interplay between Davis’s piano and Piltch’s bass is particularly strong, establishing a groove that makes the four-minute track feel cinematic in scope. It’s a standout on Temptation and essential listening for anyone curious about how she approaches the Waits catalog.
Cry If You Want To
“Cry If You Want To” shows Holly Cole at her most playfully theatrical — and the performance has a winking self-awareness that sets it apart from her more somber work. The vocal delivery is precise and dry, with timing that owes as much to spoken-word cabaret as it does to jazz. It’s a permission slip dressed up as a song, and Cole sells every word with complete conviction. This track demonstrates the range that makes her catalog so rewarding: she is not a one-note artist, and the wit she brings to this material is as impressive as the emotional depth she summons elsewhere. It’s the kind of song that makes you smile before it makes you feel.
Don’t Let the Teardrops Rust Your Shining Heart
This overlooked gem from the Holly Cole Trio’s early recordings is a minor-key wonder. The title alone is a piece of poetry, and Holly Cole honors that with a vocal performance that is both delicate and resolute. The arrangement lingers in the spaces between beats, creating a sense of suspension that perfectly mirrors the lyric’s emotional ambivalence. It’s a song about preserving tenderness in the face of heartbreak, and Cole navigates that balance with remarkable grace. If you’re building a playlist of her finest moments, this track deserves a spot near the top despite receiving less attention than some of her more famous recordings.
Blame It on My Youth
“Blame It on My Youth” is a jazz standard written by Oscar Levant and Edward Heyman in 1934, and Holly Cole’s version is everything a standard recording should be: reverent to the melody, inventive in phrasing, and emotionally honest from first note to last. Her voice on this track has a luminous quality, clear and warm, and she takes her time with each line as though discovering the lyric in real time. Aaron Davis’s piano voicings are particularly elegant here, providing a harmonic cushion that lifts Cole’s performance without overwhelming it. This is vintage Holly Cole — the jazz singer at her most refined.
Come Fly With Me
The Sammy Cahn and Jimmy Van Heusen classic gets a Holly Cole treatment that is sophisticated and swinging, full of the easy confidence that has always defined her best work. Where Sinatra’s iconic version trades in big-band swagger, Cole’s trio arrangement is more intimate — a cocktail-party charm offensive delivered in a room where everyone leans in to listen. The tempo is relaxed without being sleepy, and her phrasing has a conversational naturalness that makes the song feel freshly written. For audiophiles who enjoy hearing this material on quality equipment, it’s worth noting that the trio’s recordings reward premium headphone listening for the spatial detail in the acoustic bass and piano.
I’ve Just Seen a Face
Yes — a Beatles song, and Holly Cole does something genuinely unexpected with it. Originally a bright, tumbling folk-pop track from Help! (1965), her version slows the melody into jazz territory, revoicing the chords and letting the lyric’s breathless wonder breathe differently. It’s a daring choice, and it works precisely because she doesn’t treat it as a novelty. She finds the song’s emotional core — pure, startled, head-over-heels amazement — and delivers it with complete sincerity. Few interpretations of Beatles material in the jazz world are this successful, and it stands as one of the more surprising moments in her catalog.
Alison
Elvis Costello again, and this time Holly Cole takes on one of his most beloved early songs. “Alison” (1977) is a masterpiece of restrained heartbreak, and her version leans into that restraint completely. The piano is the emotional center of the arrangement, with Davis playing with the kind of sensitivity that matches Cole’s vocal perfectly. What’s remarkable is how she makes the song entirely her own without altering its essential character — the sadness is the same, but the color is different, a little cooler, a little more resigned. This is the kind of cover that makes you want to call the songwriter and say thank you for leaving room for this.
Take Me Home
A quiet, gorgeous album track that showcases Holly Cole’s ability to make a simple melody feel profound. “Take Me Home” is a study in vocal economy — she never pushes for effect, never oversings a single syllable. The trio’s accompaniment is equally restrained, leaving plenty of air around the notes. This is music for long drives home or slow Sunday mornings, and it has the timeless quality of something that could have been recorded in any decade. It’s a reminder that Holly Cole’s greatness isn’t just in her bold interpretations of difficult material — it’s equally present in the quiet songs that ask almost nothing and give back everything.
Little Boy Blue
“Little Boy Blue” is one of Holly Cole’s most emotionally direct recordings — a song that deals with childhood, loss, and innocence with a directness that could easily tip into sentimentality, but never does. Her vocal control here is impeccable: she finds the grief in the lyric without wallowing, and the trio’s arrangement supports that balance beautifully. It’s a track that rewards repeated listening, revealing new layers of nuance each time you return to it. As an example of how she handles emotionally charged material, this song sits alongside her very best work.
Looking for the Heart of Saturday Night
Tom Waits wrote this title track for his 1974 album, and it remains one of his most enduring early compositions. Holly Cole’s version is tender and searching, capturing the song’s restless, hopeful energy without losing its melancholy undertow. Her voice takes on a slightly lower, huskier quality here that suits the late-night setting of the lyric perfectly. The trio plays it close, staying in a soft pocket that makes the whole track feel like a memory being retrieved rather than a moment being lived. It’s one of the best examples of her ongoing dialogue with the Waits catalog.
God Will
Lyle Lovett wrote “God Will” for his 1988 album Lyle Lovett and His Large Band, and it’s a song of biblical wit and country-flavored irony. Holly Cole’s version distills it to its jazz essence, and the result is darkly funny, elegant, and ever so slightly wicked. Her timing on the sardonic passages is perfect, and she clearly relishes the song’s theological mischief. It’s one of the more unexpected choices in her recorded output, demonstrating that her interpretive curiosity extends well beyond Waits and Costello into the broader landscape of American songwriting. For listeners curious about the range of her influences, this is essential.
Invitation to the Blues
Another Tom Waits deep cut, “Invitation to the Blues” from Small Change (1976), finds Holly Cole in pure torch territory. The lyric paints a vivid diner scene with a stranger who carries her whole story in her face, and Cole inhabits it completely. There’s a cinematic quality to her delivery that makes you see the fluorescent lights, the coffee cup, the linoleum floor. The trio’s accompaniment is beautifully shadowy, all subtle pedal points and half-lit harmonies. If you want to understand why Holly Cole’s Waits interpretations are so celebrated, this recording is exhibit A. It doesn’t imitate; it translates.
Charade
The Henry Mancini classic from the 1963 film starring Audrey Hepburn and Cary Grant is one of the great film themes, and Holly Cole’s recording honors that legacy without being overshadowed by it. Her voice has an Old Hollywood glamour on this track that suits the song’s sophisticated melancholy, and the arrangement draws on the best instincts of classic jazz vocal recording. To fully appreciate the nuance of Davis’s piano work against Cole’s voice here, listening on quality earbuds with a wide soundstage makes a genuine difference — the spatial separation is remarkable. It’s a beautiful, timeless recording.
Don’t Smoke in Bed
We close with one of Holly Cole’s signature performances — a song that became central to her reputation as an interpreter of wit and intimacy. Originally written by Willard Robison and recorded by various artists in the 1940s, the song is a sleepy, slightly surreal farewell note from a woman walking out on a relationship. Cole performs it with a deadpan warmth that is entirely her own, and the trio keeps things perfectly spare. The casualness of the delivery is deceptive: this is a carefully constructed performance, every pause and inflection deliberate. It’s a perfect final note for any Holly Cole playlist — quiet, knowing, and quietly devastating.
Frequently Asked Questions
What genre is Holly Cole?
Holly Cole is primarily a jazz vocalist, though her catalog blends cabaret, pop, folk, and avant-garde influences. She works most often in a piano trio setting with pianist Aaron Davis and bassist David Piltch, and her approach to standards and covers often draws on cool jazz and West Coast jazz traditions. Her willingness to interpret rock, pop, and country material through a jazz lens has made her one of the most versatile vocalists in the contemporary Canadian music scene.
What is Holly Cole’s most famous song?
Calling You, her haunting interpretation of the Bob Telson composition from Bagdad Cafe, is widely considered her signature recording. It appeared on her landmark 1995 album Temptation and introduced her to a much wider audience. Her version of Tom Waits’s Looking for the Heart of Saturday Night and her entire Temptation album are also considered defining works.
Has Holly Cole won any awards?
Yes — Holly Cole has received multiple Juno Award nominations throughout her career, which is Canada’s premier music industry award. The Holly Cole Trio was recognized for their contributions to jazz and adult contemporary music, and Temptation in particular received widespread critical acclaim, cementing her reputation as one of Canada’s finest jazz vocalists.
Why does Holly Cole record so many Tom Waits songs?
Holly Cole has spoken publicly about her deep admiration for Tom Waits as a songwriter, describing his compositions as rich in cinematic detail and emotional complexity. Her entire album Temptation (1995) is dedicated exclusively to Waits material, featuring 17 of his songs reimagined through her jazz trio lens. She has described the theatrical, character-driven quality of his lyrics as something that particularly suits her storytelling instincts.
Is Holly Cole still performing and recording?
Holly Cole has remained active in live performance and occasional recording through the years. She continues to tour in Canada and internationally, and her catalog continues to attract new listeners through streaming platforms. Her recordings from the early-to-mid 1990s, particularly Temptation and Girl Talk, remain her most streamed and most critically discussed works.
What is the best Holly Cole album to start with?
Temptation (1995) is the near-universal recommendation for new listeners — it is cohesive, emotionally gripping, and showcases her voice and the trio at their most focused. From there, Girl Talk (1990) and Holly Cole (1998) offer excellent expansions of her sound. For listeners interested in her approach to the Great American Songbook, Dark Dear Heart (1997) is also essential.