Frank “The Voice” Sinatra, the man with the golden vocal cords, ruled the music world for years and continues to be a musical legend to this day. Known for his smooth, resonant tones and unforgettable tracks, he has won the hearts of countless fans. While selecting his top songs is almost an impossible task, here’s an attempt.

10. Love and Marriage


This iconic song, often associated with the popular TV show “Married with Children,” is one of Sinatra’s cheeriest. Its light, playful melody pairs perfectly with lyrics questioning the notion that love and marriage are inseparable.

9. I’ve got you under my skin

I've Got You Under My Skin - Frank Sinatra | Concert Collection

Featuring invigorating instrumentation and Sinatra’s irresistible vocals, this song delves into the unavoidable allure of love. The way Sinatra emphasizes the words “I’ve got you” really makes you believe he’s utterly smitten.

8. Summer Wind

Summer Wind (2008 Remastered)

This track serves as a nostalgic look back at a summer romance that faded away as swiftly as a summer breeze. Sinatra’s calm and melodic voice complements the song’s melancholy lyrics, making it a timeless tune.

7. The way you look tonight

The Way You Look Tonight (2008 Remastered)

This song is dripping with romance. It’s an ode to a loved one’s timeless beauty, and Sinatra’s voice, full of affection and admiration, makes this a go-to for romantic evenings.

6. Strangers in the Night

Frank Sinatra - Strangers In The Night

This song tells the tale of a chance encounter that leads to lifelong love. The iconic “dooby-doo’s” at the end were spontaneously improvised by Sinatra, adding a unique flair to the track.

5. Luck be a Lady

Frank Sinatra - Luck Be A Lady

Popularized by the musical “Guys and Dolls”, this song portrays gambling as a flirtatious dance with fate. Sinatra’s powerful rendition adds a distinct charm, making it one of his most recognizable tracks.

4. Fly me to the moon

Frank Sinatra - Fly Me To The Moon (Live At The Kiel Opera House, St. Louis, MO/1965)

A true auditory delight, this song features Sinatra’s smooth vocals and a jazzy arrangement. It articulates the desire to soar to unknown heights with a loved one, and with Sinatra at the helm, you feel like you’re actually floating among the stars.

3. New York, New York

Frank Sinatra - New York, New York (Live At Budokan Hall, Tokyo, 1985)

This may well be the anthem for the city that never sleeps. Sinatra’s voice, filled with bravado and pride, pays tribute to the Big Apple and the dreams it embodies. Every time you hear this song, you’ll want to pack your bags and head for New York City.

2. That’s Life

That's Life (2008 Remastered)

This song acknowledges the ups and downs of life. Sinatra sings with a blend of sarcasm, resilience, and determination. The track is both inspiring and entertaining, perfectly showcasing Sinatra’s versatility.

1. My Way

Frank Sinatra - My Way (Live At Madison Square Garden, New York City / 1974 / 2019 Edit)

The ultimate Sinatra song. “My Way” is a reflection on a life filled with both satisfaction and regret. Sinatra’s powerful and emotional rendition makes this song a universal anthem for resilience and self-respect, serving as the perfect finale for a career full of highlights.

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