Ranking the five best Frank Sinatra albums

The great Frank Sinatra is a legend in the music industry, largely due to his strong yet soulful voice, his undeniable charisma, his impeccable sense of style, and his predilection for perfection. He was also one of the most prolific artists ever, releasing well over 20 albums in his illustrious career, which spanned nearly half a century. For that reason, choosing 5 of his best is a nearly impossible task, as several great LPs will surely be left out. That being said, here is a honest-to-goodness try at ranking Sinatra’s 5 best albums.

Where Are You?

Frank Sinatra - Where Are You?

Where Are You? is Sinatra’s 13th studio album and it seamlessly blends the Hoboken, New Jersey-native’s soaring vocals with the lush, haunting, and decidedly melancholic string arrangements of the equally brilliant Gordon Jenkins. The All Music review of the album states that the setup worked like a charm, as Jenkins’ music makes Sinatra’s voice “sound rich, relaxed, and regretful”. The album features such hits as “The Night We Called It a Day,” “I Cover the Waterfront,” and “Lonely Town.”

In the Wee Small Hours

Frank Sinatra - In The Small Hours

At number 101 in Rolling Stone’s 500 Greatest Albums of All Time list is the Sinatra classic In the Wee Small Hours. Released just two years after Sinatra broke up with Ava Gardner, the album is marked by a “midnight mood of loneliness and lost love.” The Chairman of the Board seemingly channels his inner grief throughout the album, which features all-timers like “In the Wee Small Hours of the Morning,” “Mood Indigo,” “Glad to Be Unhappy,” and “When Your Lover Has Gone.”

Songs for Swingin’ Lovers!

Frank Sinatra - Songs For Swingin' Lovers

Songs for Swingin’ Lovers! is a departure from In the Wee Small Hours stylistically in that the former features up-tempo swing songs that are mainly reinterpretations of pop favorites during Sinatra’s time. Gone, too, are the feelings of grief and despair, as Ol’ Blue Eyes sings songs like “You Make Me Feel So Young” and “Pennies from Heaven” with palpable joy and unmistakable authority. The “center” of the album, though, is Sinatra’s breathtaking version of “I’ve Got You Under My Skin,” which purportedly took Sinatra 22 takes to perfect.

Come Fly With Me

Frank Sinatra - Come Fly With Me

Fun and fresh are two words that best describe this album, whose overriding theme is travel. It is Sinatra’s first album with arranger Billy May, and the partnership helped pave the way for a more playful, carefree, yet ultimately affectionate set of songs. Notably, the album strikes a perfect balance in terms of song choice, featuring upbeat swing hits and romantic ballads. Some of the LP’s best hits include “Moonlight in Vermont,” and “April in Paris,” “Isle of Capri,” “On the Road to Mandalay,” and the title track, “Come Fly With Me.”

Francis Albert Sinatra & Antonio Carlos Jobim

Francis Albert Sinatra & Antonio Carlos Jobim

Sinatra made this album in a time of great turbulence not only in his personal life, but in the country as well. But as always, the man delivered, and having fellow musical genius Antonio Carlos Jobim certainly helped. The album itself is sublime and serene, and as reported here previously on The Music Universe, it stayed at the Billboard albums chart for 28 weeks.

Again, Sinatra was quite prolific, which means that several great albums have been left out of this list. The album Come Dance with Me! comes to mind right away as it spent more than two years at the Billboard charts and includes the title track “Come Dance with Me” and the playfully sexy “Something’s Gotta Give.” The 1965 compilation album Sinatra ’65: The Singer Today deserves a shout out as well, as it features Sinatra classics like “Anytime At All,” “Somewhere in Your Heart,” and “Stay With Me.” It also contains Sinatra’s exceptional reinterpretation of “Luck Be a Lady”. PartyPoker states that the song was originally used in 1955 on the soundtrack for movie musical Guys and Dolls. Yet, despite being first performed by Robert Alda, “Luck Be a Lady” ultimately became a Sinatra signature song, along with “My Way,” “Come Fly with Me,” and many others.

Still, the five albums on this list are all great, and each is an auditory treat that showcases Sinatra at his very best.

Buddy Iahn
Buddy Iahn

Buddy Iahn founded The Music Universe when he decided to juxtapose his love of web design and music. As a lifelong drummer, he decided to take a hiatus from playing music to report it. The website began as a fun project in 2013 to one of the top independent news sites. Email: info@themusicuniverse.com