11 Underrated Frank Sinatra Songs: Secret Melodies

Hey everyone, TBone here from Level Tunes! As a DJ and a die-hard music enthusiast, I’ve always had a soft spot for the classics, and who better epitomizes that golden era than Frank Sinatra?

Today, I’m taking a delightful detour from my usual mixes to spotlight 11 underrated gems from Ol’ Blue Eyes himself. Why these songs, you ask?

Well, while we all sway to “Fly Me to the Moon” or get lost in “My Way,” there’s a trove of Sinatra tracks that don’t get the limelight they deserve.

These songs showcase his incredible range, emotion, and that timeless charm.

Whether you’re a fellow DJ looking for some unique tracks to spin or a music lover eager to explore, join me on this journey through the lesser-known but equally captivating side of Sinatra’s legendary repertoire. Let’s dive into the world of smooth melodies and classic charisma!

Here are the underrated Frank Sinatra songs that you can check out:

List Of Underrated Frank Sinatra Songs

Underrated Frank Sinatra songs in a list format:

1. “Forget Domani”

Album: “Sinatra ’65: The Singer Today” (1965)
Label: Reprise Records
“Forget Domani” is a hidden jewel from the album “Sinatra ’65: The Singer Today.” Composed by Riz Ortolani for the film “The Yellow Rolls-Royce,” this song captures Sinatra’s ability to infuse cinematic storytelling into his music. Released in 1965 under Reprise Records, it’s a track that showcases Sinatra’s smooth, expressive vocals against a backdrop of lush orchestration. The reason I’ve chosen this song is its blend of classic Sinatra charm with a cinematic touch, offering a different flavor from his more famous hits. It’s a perfect example of Sinatra’s versatility and his knack for turning any song into a personal narrative.

2. “I’ll Be Seeing You”

Album: “Point of No Return” (1962)
Label: Capitol Records
“I’ll Be Seeing You” from the 1962 album “Point of No Return” is a tender, heartfelt rendition by Sinatra. This song, originally popularized during WWII, is given a new, poignant depth by Sinatra’s emotive voice. Released under Capitol Records, it features subtle yet captivating orchestration, allowing Sinatra’s vocals to take center stage. I included this track for its emotional resonance and Sinatra’s ability to convey deep longing and sentimentality, making it a timeless piece that often goes unnoticed in his vast discography.

3. “Moonlight Serenade”

Album: “Moonlight Sinatra” (1966)
Label: Reprise Records
“Moonlight Serenade” is a standout track from the 1966 album “Moonlight Sinatra.” This song, originally an instrumental by Glenn Miller, is transformed into a vocal masterpiece by Sinatra. Under Reprise Records, Sinatra’s version adds a layer of romantic crooning to the classic melody. The reason for its inclusion in this list is its magical blend of Sinatra’s voice with the nostalgic tune, creating a dreamy, moonlit atmosphere. It’s a track that exemplifies Sinatra’s ability to reinterpret and elevate already beloved music.

4. “This Nearly Was Mine”

Album: “The Concert Sinatra” (1963)
Label: Reprise Records
“This Nearly Was Mine” from “The Concert Sinatra” album, released in 1963 under Reprise Records, is a lesser-known but powerful Sinatra performance. Originating from the musical “South Pacific,” Sinatra’s version is a showcase of his dramatic vocal prowess. The song’s orchestral arrangement, conducted by Nelson Riddle, complements Sinatra’s expressive delivery perfectly. I chose this song for its theatrical quality and Sinatra’s ability to bring a Broadway standard to life with his unique style, making it a hidden gem in his repertoire.

5. “Softly, As I Leave You”

Album: “Sinatra’s Sinatra” (1963)
Label: Reprise Records
“Softly, As I Leave You,” from the 1963 album “Sinatra’s Sinatra,” is a poignant and beautifully understated track. Released under Reprise Records, this song features Sinatra’s tender and introspective vocal interpretation of a love story ending. The choice of this song is due to its emotional depth and simplicity, which stands in contrast to Sinatra’s more grandiose numbers. It’s a testament to his ability to convey powerful emotions in a subtle and intimate manner.

6. “The Last Dance”

Album: “Come Dance with Me!” (1959)
Label: Capitol Records
“The Last Dance” from the 1959 album “Come Dance with Me!” is a vibrant and rhythmic Sinatra classic. Released under Capitol Records, this track showcases Sinatra’s ability to deliver swing tunes with an effortless charm. The song, arranged by Billy May, has an infectious energy that’s hard to resist. I included “The Last Dance” for its representation of Sinatra’s upbeat, danceable side, a facet often overshadowed by his more somber ballads. It’s a track that invites listeners to the dance floor, Sinatra-style.

7. “The September of My Years”

Album: “September of My Years” (1965)
Label: Reprise Records
“The September of My Years,” the title track from his 1965 album under Reprise Records, is a reflective and deeply moving song. Sinatra’s vocal delivery is imbued with a sense of nostalgia and introspection, perfectly capturing the essence of aging and reminiscence. This song is chosen for its poetic lyrics and Sinatra’s ability to infuse them with genuine emotion, creating a poignant and touching listening experience.

8. “When No One Cares”

Album: “No One Cares” (1959)
Label: Capitol Records
“When No One Cares” from the 1959 album “No One Cares” is a melancholic masterpiece. Under Capitol Records, Sinatra delivers this song with a raw and vulnerable emotion that’s palpable. The track’s arrangement, featuring lush strings and a gentle rhythm, complements Sinatra’s somber tone. This song is included for its emotive depth and the way it showcases Sinatra’s skill in conveying the feelings of loneliness and despair, making it a powerful and moving piece.

9. “It’s a Lonesome Old Town”

Album: “Sinatra Sings for Only the Lonely” (1958)
Label: Capitol Records
“It’s a Lonesome Old Town” from the 1958 album “Sinatra Sings for Only the Lonely” is a song that resonates with a haunting beauty. Released under Capitol Records, Sinatra’s rendition brings a melancholic depth to this classic tune. The choice of this song is due to its atmospheric quality and Sinatra’s ability to bring a sense of longing and solitude to life through his voice, creating an immersive and emotionally rich experience.

10. “Ol’ Macdonald”

Album: “Sinatra’s Swingin’ Session!!!” (1961)
Label: Capitol Records
“Ol’ Macdonald” from the 1961 album “Sinatra’s Swingin’ Session!!!” is a fun, upbeat track that showcases a different side of Sinatra. Released under Capitol Records, this song is a swingin’ take on the classic children’s tune. I chose this song for its playful energy and Sinatra’s ability to transform a familiar melody into a jazzy, toe-tapping number. It’s a testament to his versatility and his knack for bringing a fresh perspective to any song.

11. “I Could Have Told You”

Album: “No One Cares” (1959)
Label: Capitol Records
“I Could Have Told You” from the 1959 album “No One Cares” is a soulful and introspective ballad. Under Capitol Records, Sinatra’s rendition is filled with a sense of regret and melancholy. The song’s arrangement, featuring soft strings and a gentle piano, complements Sinatra’s reflective mood. This track is selected for its emotional resonance and Sinatra’s ability to convey a sense of heartfelt sorrow, making it a deeply moving and underrated piece in his collection.

Fun Facts: Underrated Frank Sinatra Songs

1. “Forget Domani”

• Oscar Winner: “Forget Domani” won the Oscar for Best Original Song in 1965 for its use in the film “The Yellow Rolls-Royce.” It’s a rare instance where a Sinatra track is directly linked to an Academy Award.

2. “I’ll Be Seeing You”

• War-Time Classic: Originally popular during WWII, “I’ll Be Seeing You” became an anthem for soldiers and their loved ones. Sinatra’s version added a new layer of nostalgia to this classic, resonating with those who remembered the war years.

3. “Moonlight Serenade”

• A Tribute to Glenn Miller: Sinatra’s vocal version of “Moonlight Serenade” is a homage to Glenn Miller, whose orchestra made the song famous. It showcases Sinatra’s respect for other music legends and his ability to reinterpret instrumental classics.

4. “This Nearly Was Mine”

• Broadway Connection: This song is from the Rodgers and Hammerstein musical “South Pacific.” Sinatra’s rendition is noted for bringing a cinematic and dramatic quality to a Broadway standard, blending the worlds of musical theatre and popular music.

5. “Softly, As I Leave You”

• An Italian Connection: Originally an Italian song, “Softly, As I Leave You” was translated into English and covered by Sinatra. This track highlights Sinatra’s affinity for Italian music, reflecting his own heritage.

6. “The Last Dance”

• Energetic Arrangement: The song’s arranger, Billy May, was known for his brassy, upbeat arrangements. “The Last Dance” is a perfect example of how his lively style complemented Sinatra’s vocals, creating a vibrant and danceable track.

7. “The September of My Years”

• Reflecting on Life: Released when Sinatra was 50, this song reflects on aging and looking back on life’s moments. It’s often seen as Sinatra’s personal reflection on his own life and career.

8. “When No One Cares”

• The Lonely Heart: This song is a standout in Sinatra’s “saloon song” repertoire, a style where he excelled at portraying a lone, introspective figure in a quiet bar setting, reflecting on past loves and losses.

9. “It’s a Lonesome Old Town”

• Emotionally Rich: Sinatra’s ability to convey a deep sense of loneliness makes this track a standout. It’s often praised for its emotional depth and Sinatra’s skill in evoking a sense of solitude.

10. “Ol’ Macdonald”

• A Swingin’ Twist: Sinatra’s unique take on the children’s song “Ol’ Macdonald” demonstrates his ability to inject a sense of fun and swing into even the most unexpected tunes, showcasing his playful side.

11. “I Could Have Told You”

• A Sense of Regret: This song is noted for its melancholic tone, with Sinatra conveying a deep sense of regret. It’s a testament to his ability to express complex emotions through his music, making even a simple ballad resonate deeply with listeners.

And there you have it, folks — a journey through the hidden treasures of Frank Sinatra’s illustrious career. These 11 songs might not top the charts, but they certainly capture the heart. Here’s to the timeless tunes of Sinatra, the ones that linger in the shadows of his spotlight. Cheers to the underrated classics!

Thanks for reading.

TBone