My Funny ValentineChet Baker1rank/position

My Funny Valentine

The gemlike ballad by Chet Baker—affectionately known as the “Prince of Cool”—is an extraordinarily famous work and a true jazz classic.

Its lyrics portray a paradoxical kind of love that cherishes everything about a slightly unusual lover—their looks and quirks alike—and this worldview harmonizes beautifully with his wistful, delicate singing voice.

The piece appears on his landmark 1954 album “Chet Baker Sings,” the first to fully capture his vocals.

It was later featured on the soundtrack of the film “Sharky’s Machine.” This is a deeply affecting performance, perfect for a quiet night when you want to immerse yourself in music alone.

Born To Be BlueChet Baker2rank/position

Chet Baker – Born to Be Blue

“Born to Be Blue” is a song by Chet Baker, the iconic West Coast jazz trumpeter and vocalist.

The title was also used for the 2015 film that portrays a portion of his life.

“Born to Be Blue” appears on his 1965 album Baby Breeze, and its bluesy piano paired with Baker’s sweet vocals gives it a chic vibe.

It’s the perfect track to enjoy on an autumn night with a drink in hand.

I Fall in Love Too EasilyChet Baker3rank/position

I Fall in Love Too Easily

Nicknamed the “Prince of Cool,” Chet Baker is a defining figure of cool jazz.

His appeal lies not only in his trumpet but also in his delicate, slightly melancholic vocals.

This signature ballad of his is a perfect fit for a long autumn night.

It captures the bittersweet feeling of falling in love easily yet never seeing it bloom, harmonizing beautifully with Baker’s fragile singing.

The piece appears on the classic 1954 album “Chet Baker Sings,” which was wildly popular at the time—so much so that he even outpaced the likes of Miles Davis in popularity polls.

An ideal choice for an autumn evening when you want to sink into a sentimental mood.

Almost BlueChet Baker4rank/position

Almost Blue

It may not be all that famous, but as a jazz ballad I absolutely want to introduce this piece.

Chet Baker, who etched his name into jazz history with his lyrical trumpet tone and wistful singing voice, yet lived a ruinous life, often chose to perform Almost Blue in his later years.

Despite its simple melody, each trumpet note speaks to you in a way that a hundred different sounds from other players could never capture.

Jazz allows for this kind of expression, too.

Time After TimeChet Baker5rank/position

Chet Baker – Time After Time

A beautiful ballad with a tinge of melancholy that truly touches the heart.

Singing of love that transcends the passage of time, this song evokes deep emotion through Chet Baker’s delicate vocals and trumpet.

Released in 1955, it was featured in the films American Gigolo and Hannah and Her Sisters, capturing the hearts of many.

Baker’s performance remains a jazz classic that has not faded with time, elegantly weaving a tale of love and loss.

It’s a perfect piece to listen to on a quiet winter night while thinking of someone dear.

Winter WonderlandChet Baker6rank/position

Chet Baker – Winter Wonderland (Rare Lp Take)

Written in 1934 by Felix Bernard and Richard Bernard Smith, this song has been performed by many artists as a classic Christmas tune.

It has a slightly stylish vibe, and no matter the arrangement, it always heightens the Christmas spirit.

Often performed not only by singers but also as an instrumental, Chet Baker’s version has a driving tempo that feels like a sleigh gliding along—very cool indeed.

Autumn in New YorkChet Baker7rank/position

CHET BAKER Autumn in New York

This is a standard number written and composed by Vernon Duke, known in Japan by the title “New York no Aki” (“Autumn in New York”).

It was originally written for the revue “Thumbs Up,” but it seems it wasn’t very popular at the time of its premiere.

Later, after Frank Sinatra sang the song, it gained popularity and came to be regarded as a standard.