Tony Bennett on Holiday cover

Tony Bennett on Holiday

Tony Bennett · 1997

59 min · 19 tracks · jazz

A collection of timeless jazz standards, infused with Bennett's warm vocals and lush orchestral arrangements, evoking nostalgia and romance.

Spotify Apple Music
Own it: Amazon eBay

Top tracks — play these first

  • →
    Solitude Start here — establishes the sonic palette early
  • →
    God Bless the Child — Bennett's rendition of this Billie Holiday classic captures the song's emotional weight, highlighting his ability to convey deep feeling through phrasing and timing.
  • →
    Good Morning, Heartache — This track features Bennett's rich vocals paired with poignant lyrics about lost love, demonstrating his skill in interpreting lyrical nuance.
  • →
    When a Woman Loves a Man — The performance showcases Bennett’s smooth delivery and connection to the emotional core of the song, making it a standout moment on the album.

Elevation

Our rating, out of 100 — and why.

AI-generated from five scored dimensions. An opinion, not a measurement.

56 /100
Foothills
Higher than 47% of albums we've rated

Bennett's interpretations and orchestration create a nostalgic yet fresh take on jazz standards.

What we noticed

  • The album features lush orchestral arrangements that complement Bennett's warm vocal delivery throughout.
  • The running time includes 19 tracks, with several songs featuring extended instrumental sections that highlight the accompanying musicians.
Composition 25% of the score
7/10

the writing — melody, harmony, structure, lyrics

Craft 20% of the score
8/10

production, performance, arrangement

Durability 25% of the score
6/10

whether it rewards returning to it

Distinctiveness 18% of the score
6/10

whether it sounds like itself

Sequencing 12% of the score
5/10

running order, pacing, length

Influence 4/10

Known within its scene. Reported but not counted — how far a record travelled describes its reception rather than the record, and a newer release has had less time to travel than an older one.

Is this for you?

Good fit if you like

  • soothing background for relaxation
  • nostalgic charm for quiet evenings
  • steady flow of heartfelt ballads
  • warm vocals for intimate moments

Maybe skip if you

  • seekers of high-energy tracks
  • prefer modern, upbeat sounds

Where this album fits

In the catalog
Deep Cut — A solid entry in his catalog, showcasing classic standards but not a standout in accessibility.
Themes
nostalgic jazz standards· Billie Holiday tribute· romantic melancholy
Career context
Released in 1997, Tony Bennett on Holiday came after a resurgence in Bennett's career during the 1990s, driven by the success of his album MTV Unplugged. This period marked a reintroduction to younger audiences and solidified his status as an enduring figure in jazz and pop music.
Stylistic neighbors
Frank Sinatra· Nat King Cole· Ella Fitzgerald
New to Tony Bennett? Find your way in →

Tracklist

  • 1 Solitude Start here 2:57
  • 2 All of Me 1:44
  • 3 When a Woman Loves a Man 3:11
  • 4 Me, Myself and I (Are All in Love With You) 2:05
  • 5 She’s Funny That Way (I Got a Woman, Crazy for Me) 4:20
  • 6 If I Could Be With You (One Hour Tonight) 2:04
  • 7 Willow Weep for Me 3:00
  • 8 Laughing at Life 3:26
  • 9 I Wished on the Moon 2:46
  • 10 What a Little Moonlight Can Do 2:45
  • 11 My Old Flame 2:55
  • 12 That Ole Devil Called Love 4:00
  • 13 Ill Wind (You’re Blowin’ Me No Good) 3:04
  • 14 These Foolish Things (Remind Me of You) 4:22
  • 15 Some Other Spring 4:41
  • 16 Crazy She Calls Me 3:53
  • 17 Good Morning, Heartache 2:37
  • 18 Trav’lin’ Light 2:33
  • 19 God Bless the Child 2:32

What to play next

Tony Bennett: The Playground
Listen next

Tony Bennett: The Playground

1998

Continues the lush orchestral sound with a playful twist, expanding on the holiday vibe.
Here's to the Ladies
Go back to

Here's to the Ladies

1995

Precedes with a focus on classic standards and showcases Bennett's vocal warmth.
Full Tony Bennett discography Where to start with Tony Bennett Artists like Tony Bennett
jazz soul

If this landed

Records by other artists that run on the same instinct.

Ella Fitzgerald Sings the Gershwin Song Book, Vol. 2

Ella Fitzgerald Sings the Gershwin Song Book, Vol. 2

Ella Fitzgerald

Shares a nostalgic approach to jazz standards, showcasing warm vocals and romantic melodies.

Love Is the Thing

Love Is the Thing

Nat King Cole

Infuses jazz with romantic melancholy, featuring lush arrangements and soothing vocals.

Lady in Satin

Lady in Satin

Billie Holiday

Captures a similar emotional depth with soulful interpretations of standards, embodying nostalgia and longing.

Reference: Wikipedia · MusicBrainz · Wikidata