Learn How to Play the Best Frank Sinatra Guitar Songs

Frank Sinatra may be known as one of the greatest crooners of all time, but many of his classics also sound amazing on acoustic guitar.

This page features 10 popular Frank Sinatra songs you can learn to play, including "Fly Me To The Moon," "My Way," and "Strangers In The Night."

Each lesson includes the chords, rhythm tips, and a video demo to help you get started, whether you're strumming at home or performing for friends.

Grab your guitar and bring some swing and soul to your playing with these timeless hits.

Both Sides, Now was written by Canadian singer-songwriter Joni Mitchell and first gained widespread attention through Judy Collins' hit recording in 1967, which introduced the reflective folk classic to a broad audience.

Frank Sinatra chose the song for his 1968 album Cycles, slightly altering the title to "From Both Sides Now." Although never released as a single, Sinatra's interpretation demonstrated his willingness to embrace contemporary songwriting during the late 1960s, introducing Mitchell's work to a new generation of traditional pop listeners.

An interesting footnote to the recording sessions is that eleven songs were completed in approximately three hours, although one track was ultimately left off the finished album. Sinatra's version remains a distinctive and often-overlooked interpretation of one of Joni Mitchell's most enduring compositions.

Fly Me To The Moon  was written by Bart Howard in 1954, who famously joked that it had taken him 20 years to learn how to write a song in 20 minutes.

Originally titled "In Other Words," the romantic standard gradually became better known by its opening lyric, eventually prompting Howard to officially rename it Fly Me to the Moon. Frank Sinatra recorded what would become the song's definitive version for his 1964 album It Might as Well Be Swing, accompanied by Count Basie and his Orchestra under the direction of legendary arranger Quincy Jones.

Although never released as a commercial single, Sinatra's swinging interpretation became one of his signature recordings and later gained worldwide recognition after being associated with NASA's Apollo space missions, earning its place among the most celebrated standards of the twentieth century.

I've Got You Under My Skin  was written by Cole Porter for the 1936 Broadway musical Born to Dance, where it was first performed by Virginia Bruce. The song quickly became a popular standard and was recorded by several artists during the late 1930s, including Ray Noble, Hal Kemp, and others, before Frank Sinatra made it his own.

Sinatra first recorded the song in 1946, but it was his celebrated 1956 version for the album Songs for Swingin' Lovers! that became the definitive recording. Featuring the unforgettable arrangement by Nelson Riddle, complete with its dramatic orchestral crescendo and trombone solo by Milt Bernhart, the recording is widely regarded as one of the greatest vocal performances of Sinatra's career.

He continued to perform and record the song throughout the 1960s, including memorable live versions with Count Basie and his orchestra at the legendary Sands Hotel in Las Vegas.

My Way began life as the French song "Comme d'habitude," written by Claude François and Jacques Revaux. While vacationing in France during the late 1960s, Paul Anka heard the song and immediately recognized its potential.

He secured the English-language rights for a symbolic $1, while ensuring the original writers continued to receive their royalties, then created an entirely new set of lyrics with Frank Sinatra specifically in mind. Sinatra recorded the song in one take on December 30, 1968, for the album My Way, before heading to a New Year's Eve engagement at the legendary Sands Hotel in Las Vegas.

Although the recording became Sinatra's signature song and one of the most celebrated recordings of his career, he later admitted that he eventually grew weary of performing it, despite its enduring popularity with audiences around the world.

Nice 'n' Easy was written by Alan Bergman, Marilyn Bergman and Lew Spence and became the title track of Frank Sinatra's acclaimed 1960 album of the same name. Although the album is remembered as one of Sinatra's finest collections of romantic ballads, "Nice 'n' Easy" stands apart as its only up-tempo swing recording, providing a lively contrast to the otherwise relaxed mood of the album.

Released as a single, the song reached No. 60 on the Billboard Hot 100, while the Nice 'n' Easy album itself proved far more successful, spending several weeks at No. 1 on the Billboard album chart.

Sinatra continued performing the song throughout his career, and it remains one of the signature recordings from his celebrated Capitol Records years.

Please Don't Talk About Me When I'm Gone was written by Sam H. Stept, Sidney Clare and Bee Palmer and first became popular during the early 1930s, quickly establishing itself as a favorite among jazz and swing performers.

Over the decades, the standard has been interpreted by an impressive list of artists, including Ella Fitzgerald, Louis Armstrong, Sammy Davis Jr., Dean Martin, and Mose Allison, each bringing their own style to the timeless melody. Frank Sinatra recorded his version in 1961 for the album Sinatra Swings (released in the UK as Swing Along with Me), although the recording was never issued as a commercial single.

Sinatra's relaxed vocal delivery and swinging arrangement made it a natural fit for his repertoire, and today it remains one of the hidden gems from his early 1960s recordings.

Something Stupid was written by C. Carson Parks and was first recorded in 1966 by Carson and Gaile, a husband-and-wife duo featuring the songwriter and his wife, Gaile Foote. Although the original recording attracted modest attention, the song became an international sensation when Frank Sinatra and his daughter Nancy Sinatra recorded it as a duet in 1967.

Released on Frank's album The World We Knew, the single reached No. 1 on both the Billboard Hot 100 and the UK Singles Chart, becoming the first father-daughter duet ever to top the U.S. charts.

Its warm, conversational style and memorable melody have helped it remain one of the most beloved duets in popular music, with later recordings by artists such as Robbie Williams and Nicole Kidman introducing the classic to a new generation.

Strangers In The Night was composed by Bert Kaempfert, with English lyrics by Charles Singleton and Eddie Snyder. The melody was originally written for the 1966 film A Man Could Get Killed and was first offered to several artists before becoming associated with Frank Sinatra. One story often told is that Greek singer Melina Mercouri felt the song would be better suited to a male vocalist, helping pave the way for Sinatra's recording.

Released in 1966, Sinatra's version became an international sensation, reaching No. 1 on both the Billboard Hot 100 and the UK Singles Chart. The recording also earned Grammy Awards for Record of the Year, Best Male Vocal Performance, and Best Arrangement Accompanying a Vocalist, while the album of the same name became one of the biggest successes of Sinatra's career.

Today, Strangers in the Night remains one of his most recognizable and enduring signature recordings.

That's Life was written by Dean Kay and Kelly Gordon and first recorded by Marion Montgomery in 1965, although it was O.C. Smith's soulful version that brought the song to Frank Sinatra's attention.

According to the story, Sinatra was so impressed after hearing it on the radio that he pulled his car to the side of the road and phoned his daughter Nancy Sinatra to find out who published the song so he could record it himself. Released in 1966 as the title track from the album That's Life, Sinatra's powerful interpretation climbed to No. 4 on the Billboard Hot 100 and No. 3 in Canada, becoming one of the defining recordings of his later career.

The song has since been covered by numerous artists, including Aretha Franklin, Van Morrison, and David Lee Roth, confirming its place as one of the enduring classics of the Great American Songbook.

The Lady Is a Tramp was written by the legendary songwriting team of Richard Rodgers and Lorenz Hart for the 1937 Broadway musical Babes in Arms. The witty, swinging number playfully pokes fun at New York's high society, celebrating a carefree lifestyle over wealth, fashion and social convention.

Frank Sinatra recorded what many consider the definitive version for the soundtrack of the 1957 film Pal Joey, where he famously performs the song opposite Rita Hayworth. Featuring a vibrant swing arrangement, Sinatra's recording became one of the highlights of both the film and the soundtrack, helping establish the song as a permanent fixture in his concert repertoire.

Decades later, The Lady Is a Tramp remains one of Sinatra's most recognizable up-tempo recordings and a timeless example of the Great American Songbook.

Young At Heart was written by Johnny Richards (music) and Carolyn Leigh (lyrics) specifically for the 1954 Warner Bros. film of the same name. Frank Sinatra recorded the song in 1953, and it quickly became one of his biggest early hits, reaching No. 2 on the U.S. charts and No. 12 in the United Kingdom.

The song proved so popular during production that the film—originally titled Bachelor Girl—was renamed Young at Heart, starring Frank Sinatra and Doris Day, with the recording featured over both the opening and closing credits. Sinatra later revisited the song for his 1963 album Sinatra's Sinatra, recording a new version for his Reprise label.

Over the decades, the timeless standard has also been performed by artists including Bing Crosby, Barry Manilow, and Michael Bublé, while Dick Van Dyke delighted audiences in 2017 by recording the song at age 90, using one of Sinatra's original studio microphones.