Top 10 Frank Sinatra Songs

Photo: English: Photographer uncredited and unknown. Distributed by the photo department of CBS., Public domain, via Wikimedia Commons

Our Top 10 Frank Sinatra Songs list looks to do the impossible in choosing our ten favorite Frank Sinatra songs, or at least 10 of the most popular and successful Frank Sinatra songs ever recorded. And that’s just it, how should we pick them? Should it be based on number one singles, record sales, radio airplay, or just the most popular ones? In the end, we went with a mix of all those factors.

We also tried to cover multiple time periods, as Frank Sinatra released new studio albums for six consecutive decades. He released 297 singles over a stretch of seven straight decades, starting with his first single released in 1939 entitled “From the Bottom of My Heart,” to his final single release in 1993 from his Duets album entitled “I’ve Got You Under My Skin,” which was a duet between Frank Sinatra and U2’s Bono.

Frank Sinatra is easily one of the most influential and famous artists of all time. He started out during a time period when songwriters wrote songs and professional singers sang them. This was long before the arrival of the singer-songwriter era, although of course, there were exceptions. What made Frank Sinatra so special, especially as he grew older, was his phrasing. The man could sing his heart out when he was younger, but time and experience had given his voice the power to speak to millions. And most importantly, in a way that every person believed what he sang. That’s brilliant phrasing. Along with that voice came an image that was incredibly respected. The last thing you wanted to do was say something bad about Frank Sinatra.

Frank Sinatra’s phrasing had a profound impact on artists of all eras, including rock and roll. His recordings were studied by many rock stars, including Bruce Springsteen, Tom Waits, Billy Joel, and the Beatles. The passion in his vocals that told the story of the blues and the one that got away so often clearly inspired many rock and roll songwriters. This is why we include artists like Frank Sinatra on classicrockhistory.com. It is essential in making connections when studying the history of rock and roll.

Once again, it was really tough to pick just ten Frank Sinatra songs for a top 10 list. To ease the burden a bit, we also included a list of songs that should have also been in the top 10 below the top 10 list. For a long time, Frank Sinatra fans will undoubtedly be missing songs from both lists. Nonetheless, for those who are first discovering the music and life of Frank Sinatra, we think this article will serve as a great starting point to get to know the music of an artist who was one of the greatest ever.

# 10 – Learnin’ The Blues – 1955

We open up our top 10 Frank Sinatra songs list with the spectacular recording of the song “Learnin’ The Blues.” This is probably the only song on this top 10 list that might not be instantly recognizable to the 65-and-younger crowd of Frank Sinatra fans. It was one of those Frank Sinatra songs that did not become a standard. So in a way, this is a present to those who love Frank Sinatra but don’t really know this one track. Still, there had to be a very good reason for including it on this tough-to-choose Top 10 Frank Sinatra songs list. There are two big ones.

Frank Sinatra’s recording of Dolores “Vicki” Silvers’s song “Learnin’ The Blues” was Frank Sinatra’s first number-one single for Capitol Records. Sinatra had previously celebrated number-one singles during his Columbia years, but his first Capitol Records number-one single was a big deal. “Learnin’ The Blues,” was a huge hit in 1955. It turned on many new fans to the music of Frank Sinatra. Many fans, including this writer, would argue that it was Frank Sinatra’s Capitol years, from 1953 to 1962, when he released the best material of his career.

“Learnin’ The Blues” also paved the way for the everyman image that Frank Sinatra would explore in many of his Capitol recordings, and especially his Reprise releases. It was the man sitting alone at the bar, drowning his sorrows in a glass of gin, wondering what if. That was very appealing to many Americans who knew struggle all too well. A new connection had formed between Frank Sinatra and his fans on the song “Learnin’ The Blues.” It was a pivotal point in his career.

# 9 – Strangers In The Night

And speaking of the Reprise Years….. At number nine on our Top 10 Frank Sinatra songs list is another number-one Frank Sinatra song, “Strangers In The Night.” This was one of Frank Sinatra’s most successful single releases of his career for many reasons. The song was released on one of everyone’s favorite Frank Sinatra albums also titled Strangers In The Night. The album was released in 1965.

The single “Strangers In The Night” hit number one on the US Billboard Hot 100 in 1965. The song also reached number one on the Billboard Adult Contemporary, US Cash Box, and United Kingdom pop charts. The song “Strangers In The Night” also won a Grammy Award for Record Of The Year. The song won two other Grammy Awards, including Best Male Pop Vocal Performance and Best Arrangement Accompanying a Vocalist or Instrumentalist. This was one of the biggest single releases of the 1960s.

# 8 – Fly Me To The Moon

There are two definite versions of the classic song “Fly Me To The Moon.” First is Tony Bennett’s breathtaking ballad version, and the second is Frank Sinatra and Count Basie’s big swinging recording. “Fly Me To The Moon” was released on the Frank Sinatra album It Might as Well Be Swing. The album was released in 1964. “Fly Me To The Moon” has been recorded by major-label artists more than 500 times. Yet none of those other versions was ever played by NASA astronauts orbiting the Moon during the Apollo 10 and 11 missions, as Frank Sinatra’s version was. Try topping that!

# 7 – One For My Baby

It’s a quarter to three, and you know what comes next. Set ’em up, Joe! There was no way we could not include this legendary Frank Sinatra song “One For My Baby.” Those words “set em up Joe,” would be repeated millions of times by the down and out looking to escape the pain of lost love in a shot glass of Johnny Walker. He doesn’t even have to explain what happened; we know what he’s feeling, we get it, we feel it, we understand it, we lived it. Set ’em up, Joe!

# 6 – Angel Eyes

At number six on our top 10 Frank Sinatra songs list, we turn one more time to the great Sings for Only the Lonely album released in 1958. The classic song “Angel Eyes” is the ultimate blues song that does not follow blues song chord changes. This is one of Frank Sinatra’s most emotional torch songs that he ever recorded. The song was written by Matt Dennis and Earl Brent. It has been covered by hundreds of artists, but Sinatra’s version is the standard they all look up to.

# 5 – You Make Me Feel So Young

At the halfway point on our Top 10 Frank Sinatra songs list is the swinging recording “You Make Me Feel So Young.” The song was released on the fantastic album entitled Songs for Swingin’ Lovers! The album was released in 1956 on Capitol Records. The musical arrangement was done by the famous bandleader and musical conductor and arranger Nelson Riddle. This was a true gem!

# 4 – I’ve Got You Under My Skin

Frank Sinatra worked with many bandleaders throughout his career. However, the pairing of Frank Sinatra with the famous Count Basie and his orchestra produced two legendary studio recordings. One of our favorite live albums of all time was Sinatra At The Sands with Count Basie and His Orchestra. This was Frank Sinatra’s first live album, and it really captured the live concert Sinatra experience.

Produced by Quincy Jones, the album sounded amazing, as Count Basie’s band delivered an incredibly full, tight, swinging sound that wrapped itself around Frank Sinatra. The song “I’ve Got You Under My Skin” has remained one of Frank Sinatra’s signature songs. The version recorded live at the Sands with Count Basie is simply to die for.

# 3 – Summer Wind

Frank Sinatra’s song “Summer Wind” was released on the grand Strangers in the Night album in 1965. The song served as the follow-up single to Sinatra’s number one record, “Strangers In The Night.” When the song Summer Wind” was first released, it peaked at number twenty-five on the US Billboard Hot 100. However, it reached number one on the US Billboard Adult Contemporary Chart.

The song found a brand-new audience and became a much bigger part of pop culture in 1984, when it was featured in the opening credits of the film The Pope of Greenwich Village. From that point on, the song fueled Sinatra’s legacy for a younger audience, as “Summer Wind” continued to appear in motion pictures, television shows, and commercials.

# 2 -Theme From New York, New York

Well, we are probably a little biased towards this one being from New York. If you live in New York or have ever lived in New York, you would understand just how big this song was and still is in New York. The song was written for the Martin Scorsese motion picture New York, New York in 1977. The original version was sung by Liza Minnelli. Frank Sinatra recorded the song two years later for his album Trilogy: Past Present Future. Once Sinatra recorded it, the song became his.

# 1 – My Way

In the number one spot on our Frank Sinatra songs list is a song that became Frank Sinatra’s signature after 1969. Even when he got sick of the song, he couldn’t get rid of it. “My Way” was just too associated with Sinatra, and everybody always wanted to hear him sing it. My Way was not a 100 percent original song. The song’s origins date back to a melody written by Claude François and Jacques Revaux, titled “Comme d’habitude.”

Frank Sinatra’s friend, the legendary Paul Anka, wrote new lyrics for the song and gave them to Sinatra to record. Entitled “My Way,” the song would become Frank Sinatra’s signature song for the rest of his life. It spent almost a year and a half in the United Kingdom’s Top 40, becoming the second-longest-running song of all time in the top 40. In the United States, charts could not even gauge the song’s popularity over the past fifty years.

These are other great Frank Sinatra songs that we wish we could have put in the top 10 if room allowed. All the ones below are fabulous recordings that cover a large period of time, from 1940, when Sinatra was with the Tommy Dorsey Orchestra, to the last great Frank Sinatra album released in 1981, entitled Bang Bang She Shot Me Down.

# – I’ll Never Smile Again – 1940 – With Tommy Dorsey

# – Nancy (With The Laughing Face) -1945

# – Someone To Watch Over Me – 1946

# – Mam’selle – 1947

# – Autumn In New York -1949

# – April In Paris – 1951

# – I’ve Got The World On A String -1953

# – Young At Heart -1954

# – Three Coins In A Fountain -1954

# – Love And Marriage -1955

# – Hey Jealous Lover – 1956

# – All The Way – 1957

# – Witchcraft – 1957

# – My Blue Heaven -1961

# – The Second Time Around – 1961

# – My Kind Of Town – 1964

# – It Was A Very Good Year – 1965

# – That’s Life – 1966

# – Something Stupid (With Nancy) -1967

# – Cycles – 1968

# – You Will Be My Music – 1973

# – Good Thing Going(Going Gone) – 1981

Updated January 31, 2026