Frank Sinatra Popular Songs Ranking [2026]

Strangers In The NightFrank Sinatra1rank/position

Frank Sinatra – Strangers In The Night

Frank Sinatra’s signature work released in 1966 distills the allure of the MOR genre.

Set against sophisticated strings and horns, this piece quietly portrays the emotions of two people who meet by chance on a city night—a gem of a love ballad depicting mature romance.

Sinatra’s seasoned voice envelops the listener with an intimate, conversational warmth, and the “doo-be-doo-be-doo” line near the end provides a memorable accent.

Originally an instrumental composed by Bert Kaempfert for the film A Man Could Get Killed, it was quickly fitted with English lyrics and recorded.

Winning Record of the Year at the 1967 Grammy Awards, this track is perfect for unwinding after work or savoring a quiet evening.

My WayFrank Sinatra2rank/position

My Way (2008 Remastered)

If there’s a grand ballad befitting life’s milestones, it has to be this one: Frank Sinatra’s signature classic, “My Way.” Paul Anka wrote the English lyrics to a French original, and it was released to the world in March 1969 as the album My Way.

With its powerful message about having lived life on one’s own terms, it’s a perfect gift for someone retiring or setting out toward a new dream.

In 2000, it was inducted into the Grammy Hall of Fame, cementing its enduring legacy.

The piece begins with a gentle, spoken-like delivery and builds to a soaring finale with full orchestra—truly moving.

Play it at the end of a farewell party, and the room is sure to be filled with warmth.

Be sure to check it out.

Fly Me to the MoonFrank Sinatra3rank/position

Fly Me To The Moon (2008 Remastered)

An immortal masterpiece by Frank Sinatra that layers a yearning for the vast cosmos with a blazing passion for love.

The original elegant waltz is famously transformed by arranger Quincy Jones into a bold, dynamic 4/4 swing.

Riding on the brilliant performance of the Count Basie Orchestra, Sinatra’s smooth vocals resonate with effortless charm.

Included on the classic album “It Might as Well Be Swing,” released in August 1964, the song is also linked to a dreamy anecdote: it reached the Moon with Apollo 11 in 1969.

Many will recognize it as the ending theme of the anime Evangelion.

It’s the perfect track when you want to feel your spirits lift and your heart skip with excitement.

Let It SnowFrank Sinatra4rank/position

Let It Snow! Let It Snow! Let It Snow!

“Let It Snow” is a famous American Christmas song released in 1945, and it has been covered by many artists.

In 1950, Frank Sinatra covered it, turning it into a stylish track with jazzy chorus arrangements.

It lifts your spirits and is a perfect song for the Christmas season.

In 2020, Frank Sinatra’s official YouTube channel released a newly produced animated music video to coincide with the holiday season.

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Hamada Takuya

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Jingle BellsFrank Sinatra5rank/position

Frank Sinatra – Jingle Bells (Official Music Video)

That cheerful melody you always hear when the Christmas season arrives.

When you listen to it in Frank Sinatra’s voice, it resonates even more deeply.

Featured on his 1948 album “Christmas Songs by Sinatra,” this piece portrays the joy of dashing through the snow in an open sleigh.

Sinatra’s smooth vocals beautifully capture the essence of this festive tune.

With its lively rhythm and catchy lyrics, it’s perfect for a karaoke pick.

Sing it with your sweetheart and it might just bring the two of you closer.

It’s a great choice for anyone who wants to enhance a romantic winter atmosphere, even if you’re not confident in your English.

Come Fly With MeFrank Sinatra6rank/position

Come Fly With Me (2008 Remastered)

This is the smash hit “Come Fly With Me” by jazz singer Frank Sinatra.

It was released in 1958.

In Japan, it was used as the ending theme for the film “Happy Flight,” starring Haruka Ayase.

Frank Sinatra enjoyed enormous popularity at the time.

This is a song that lets you fully savor his handsome, velvety vocals.

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Yoimachi Jēn

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As Time Goes ByFrank Sinatra7rank/position

Frank Sinatra – As Time Goes By (Casablanca)

Casablanca, a romantic film starring Humphrey Bogart and Ingrid Bergman, was produced and released during World War II.

Humphrey Bogart’s line in the film, “Here’s looking at you, kid,” is very famous.

The movie’s theme song is “As Time Goes By.”