11 Sad Songs by Frank Sinatra: Feel the Blues

Hey there, music lovers and fellow DJs! It’s TBone here, the heartbeat behind Level Tunes.

With 20 years in the music industry, I’ve spun records, curated playlists, and shared the soundtracks that move our souls.

Today, I’m diving deep into the emotional world of Frank Sinatra, a legend whose voice has painted the backdrop of countless memories. I’ve always had a soft spot for the crooner genre, and Sinatra, with his unparalleled ability to convey heartache, has been a constant on my playlists.

So, I’ve decided to share with you my personal list of 11 sad Sinatra songs that have touched me deeply. These tracks aren’t just songs; they’re stories, emotions, and experiences wrapped in melody.

Whether you’re a die-hard Sinatra fan or just love to feel the music, these selections promise to take you on a journey through the tender, poignant moments of Ol’ Blue Eyes’ career. Let’s dive into the heartstrings of Sinatra’s world together.

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

List Of Sad Songs by Frank Sinatra

Sad songs by Frank Sinatra in a list format:

“In the Wee Small Hours of the Morning”

Written by David Mann and Bob Hilliard, “In the Wee Small Hours of the Morning” is the title track from Sinatra’s 1955 album released under Capitol Records. This song, a cornerstone of Sinatra’s “In the Wee Small Hours” album, encapsulates the essence of loneliness and longing like no other. Its release marked a pivotal moment in Sinatra’s career, showcasing his ability to convey deep emotional landscapes. The lush orchestration, arranged by Nelson Riddle, perfectly complements Sinatra’s smooth, melancholic vocals. I chose this song for its hauntingly beautiful melody and Sinatra’s ability to make you feel the solitude of those early morning hours. The way his voice intertwines with the soft, slow strings pulls at the heartstrings, making it a timeless classic for those reflective, late-night moments.

“One for My Baby (and One More for the Road)”

A masterpiece by Harold Arlen and Johnny Mercer, “One for My Baby (and One More for the Road)” is featured on the 1958 album “Frank Sinatra Sings for Only the Lonely,” another gem under Capitol Records. This song is the epitome of a late-night lament to a bartender, capturing the raw, unfiltered emotion of someone pouring out their heart along with their drink. Sinatra’s interpretation is nothing short of legendary, delivering each line with a depth of feeling that’s almost tangible. The minimalist arrangement, led by Nelson Riddle, allows Sinatra’s voice to take center stage, showcasing his unique ability to tell a story through song. I’m drawn to the narrative quality of this track, the way Sinatra brings to life the character’s solitude and despair, making it an unforgettable piece of musical storytelling.

“Angel Eyes”

Also from “Frank Sinatra Sings for Only the Lonely” (1958, Capitol Records), “Angel Eyes” is a haunting ballad composed by Matt Dennis with lyrics by Earl Brent. Sinatra’s rendition of this song is widely regarded as one of his finest performances, thanks to its lyrical depth and the emotional intensity he brings to the recording. The song’s arrangement, dark and moody, sets the perfect backdrop for Sinatra’s voice as he sings about the pain of lost love. What makes “Angel Eyes” stand out is not just the beautiful, melancholic melody, but also Sinatra’s ability to convey a sense of profound loss and longing. The closing line, “Excuse me while I disappear,” leaves a lasting impact, embodying the song’s theme of isolation. This track is a personal favorite for its intricate blend of melody, lyrics, and Sinatra’s unparalleled emotive expression.

“I’m a Fool to Want You”

“I’m a Fool to Want You” is a deeply personal song for Sinatra, co-written by him, Jack Wolf, and Joel Herron. Featured on the 1957 album “Where Are You?” under Capitol Records, this song delves into the complexities of love and longing. Sinatra’s performance is raw and heartfelt, reflecting his own tumultuous relationship with Ava Gardner. The orchestration, arranged by Gordon Jenkins, complements Sinatra’s vulnerable delivery with lush, somber strings. I chose this song for its emotional honesty and Sinatra’s ability to convey the torment of wanting someone you can’t have. His delivery is so authentic that it resonates on a personal level, showcasing his gift for connecting with listeners through shared human experiences.

“Only the Lonely”

Title track of the 1958 album “Frank Sinatra Sings for Only the Lonely,” “Only the Lonely” is a song composed by Sammy Cahn and Jimmy Van Heusen. This album is often cited as Sinatra’s greatest, with this track highlighting his ability to embody the loneliness and despair of the human condition. The orchestral arrangement by Nelson Riddle provides a lush, dramatic backdrop that enhances the song’s emotional weight. Sinatra’s interpretation is masterful, delivering each word with a depth of feeling that’s both captivating and heart-wrenching. I’m drawn to this song for its poignant lyrics and Sinatra’s performance, which together create a powerful expression of solitude and longing.

“What’s New?”

“What’s New?” is a song from the 1959 album “No One Cares,” again a collaboration with Capitol Records and arranged by Gordon Jenkins. Composed by Bob Haggart with lyrics by Johnny Burke, this song explores themes of heartbreak and loneliness. Sinatra’s rendition is notable for its reflective, introspective mood, complemented by Jenkins’ lush, string-laden arrangement. I admire how Sinatra transforms the song into a narrative of personal introspection, his voice conveying a deep sense of resignation and melancholy. This track stands out for its beautiful melody and Sinatra’s emotive delivery, making it a perfect addition to any collection of sad songs.

Fun Facts: Sad Songs by Frank Sinatra

“In the Wee Small Hours of the Morning”

• Fact 1: The album “In the Wee Small Hours” is often considered one of the first concept albums in music history, with all the songs revolving around themes of loneliness, lost love, and introspection.
• Fact 2: This song, and the album it belongs to, marked a significant turning point in Sinatra’s career, helping to reestablish him as a major artist after a period of professional decline.

“One for My Baby (and One More for the Road)”

• Fact 1: “One for My Baby” is one of Sinatra’s signature songs, often performed as the closing number in his live shows, creating an intimate “saloon song” atmosphere even in large venues.
• Fact 2: The song is set in a bar and addresses a bartender named Joe, which has led to a popular belief that every bartender should be called Joe, at least in the context of this song.

“Angel Eyes”

• Fact 1: Sinatra often referred to “Angel Eyes” as his favorite ballad, and it was a staple in his concerts, often highlighted by a dramatic stage setup where all lights would be turned off except for a single spotlight on him.
• Fact 2: The song’s ending line, “Excuse me while I disappear,” is iconic and was Sinatra’s way of concluding the performance of this song in a manner that left audiences in awe of the emotional journey he had taken them on.

“I’m a Fool to Want You”

• Fact 1: Sinatra recorded “I’m a Fool to Want You” shortly after his tumultuous separation from Ava Gardner, and it’s said that he was very emotional during the recording sessions, which added to the depth and authenticity of his performance.
• Fact 2: Sinatra was so connected to the song that he re-recorded it several years later for his “Sinatra & Strings” album (1962), offering a slightly different interpretation that still retained the song’s emotional core.

“Only the Lonely”

• Fact 1: The “Only the Lonely” album cover features Sinatra as a sad clown, which is a visual representation of the album’s themes of loneliness and the sadness behind the entertainment industry’s glamour.
• Fact 2: This album won the Grammy Award for Best Album Cover, highlighting not just the musical but also the visual impact of Sinatra’s work on popular culture.

“What’s New?”

• Fact 1: “What’s New?” is actually a song from the 1930s, originally an instrumental track. The lyrics were added later by Johnny Burke, making it a perfect fit for Sinatra’s exploration of themes of heartbreak and longing decades later.
• Fact 2: The album “No One Cares” is considered by many fans and critics to be one of Sinatra’s most somber and emotionally resonant albums, with “What’s New?” being a standout track for its melancholic beauty.

“Goodbye”

• Fact 1: “Goodbye” is one of the few tracks where Sinatra collaborated directly with the song’s composer, Gordon Jenkins, for the arrangement, creating a deeply personal and reflective musical piece.
• Fact 2: Despite being less known than some of Sinatra’s other sad songs, “Goodbye” is often cited by Sinatra aficionados as a hidden gem that showcases his ability to convey deep emotional narratives.

And there you have it, a journey through the melancholy magic of Frank Sinatra’s most poignant songs. These tracks are more than just music; they’re emotional experiences, each telling a story that resonates deeply. Dive into Sinatra’s world, and let these songs touch your heart.

Thanks for reading.

TBone