Miles Davis Popular Songs Ranking [2026]

My Funny ValentineMiles Davis16rank/position

Miles Davis – My Funny Valentine

When winter comes, this is the jazz standard you can’t help but want to listen to.

It’s a song about a beloved sweetheart—Mr.

Valentine—and it’s especially often performed in the lead-up to Valentine’s Day.

While it’s frequently sung by vocalists, Miles Davis’s richly expressive trumpet tone also suits the piece perfectly, doesn’t it? With lyrics that say “stay just the way you are,” it feels like a song that would make a lovely gift to a cherished partner during the Christmas season.

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Hirakawa Masako (Bōkarisuto: Sakata Mizumako)

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Round MidnightMiles Davis17rank/position

Miles Davis Quintet – ‘Round Midnight

A jazz standard composed by pianist Thelonious Monk.

The piece was used as the title track for the fictional film “Round Midnight,” which stars veteran saxophonist Dexter Gordon and centers on an American jazz musician living in Paris.

Monk himself recorded the tune in various versions, and its chord progression also appears in multiple variants, making it a curious piece for which it’s hard to determine which performance should be considered the standard.

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HATSUMI

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StuffMiles Davis18rank/position

Miles Davis – Stuff (1/2)

From the 1968 album Miles in the Sky.

It’s the opening track of the album, yet it stays cool from start to finish.

Tony Williams’s drumming is striking, and Miles’s trumpet heightens the sense of unease.

Herbie’s electric piano is razor-sharp, too.

It’s a track where truly cool, stylish players come together.

My Funny ValentineMiles Davis19rank/position

Miles Davis – My Funny Valentine 1964 Milan, Italy

Known for Miles Davis’s trumpet performance, this piece is a quintessential jazz standard.

Its richly expressive melodic lines and wistful atmosphere are distinctive, giving it a deep, resonant appeal for listeners.

A live recording made in New York in February 1964 was released the following May as the album “My Funny Valentine: Miles Davis in Concert,” earning high praise among jazz fans.

It’s also approachable for beginning saxophonists, who can enjoy practicing its relaxed tempo and beautiful harmonies.

Perform this song, imbued with an adult sophistication, and you’re sure to captivate your audience.

Autumn LeavesMiles Davis20rank/position

Miles Davis – Autumn Leaves (Live at Salle Pleyel, Paris Oct 1, 1964)

Miles Davis, whose restrained trumpet tone reshaped the course of jazz.

Among his many classic performances, this is the one I want to savor on a long autumn night.

His cool, lyrical trumpet eloquently tells the story of a world where fallen leaves symbolize a love that has passed and the lyrics cherish its memories.

You can clearly hear the influence of the pianist Ahmad Jamal—whom Davis revered so much that he declared, “I got all my inspiration from him.” This rendition was recorded in March 1958, and the famous take appears on alto saxophonist Cannonball Adderley’s masterpiece Somethin’ Else.

Be sure to give it a listen as a companion to a quiet, contemplative evening.