You know that feeling when you hear a song and you’re 100% sure you know who sang it, only to realize the "obvious" answer is actually a bit of a trick? That’s exactly what happens with Frank Sinatra Swinging on a Star. Most people associate that catchy, whimsical tune about pigs and monkeys with Bing Crosby. And they should! Bing won an Oscar for it in 1944. But if you’ve ever found yourself humming the Sinatra version, you aren't crazy.
He did record it.
It just took him twenty years to get around to it.
Frank didn't touch the song when it was a chart-topping juggernaut during World War II. At that time, he was the skinny kid from Hoboken trying to claw his way out of Bing’s enormous shadow. Singing Bing’s signature song back then would have been professional suicide, or at least a very bad look. But by 1964, things were different. Sinatra was the Chairman of the Board. He owned the label. He did whatever he wanted.
Why Frank Sinatra Swinging on a Star Finally Happened in 1964
The 1960s were a weird time for the Rat Pack. Rock and roll was eating the world, and the old guard had to figure out how to stay relevant without looking like they were trying too hard. Frank’s solution? The album Academy Award Winners.
Basically, he decided to take a victory lap through the history of film music.
This is where Frank Sinatra Swinging on a Star finally makes its entrance. The track was recorded on January 28, 1964. If you listen closely to the Reprise recording, you can hear a massive difference between Frank’s vibe and the original 1944 Bing Crosby version. Bing’s was a lesson for kids—sweet, instructional, very "Father O'Malley."
Frank? Frank makes it swing.
Working with the legendary Nelson Riddle, Sinatra turned a nursery-rhyme-adjacent pop song into a mid-tempo masterpiece. It’s got that classic Riddle "walking" bassline and a brass section that punches through the melody. Honestly, Sinatra sounds like he's having a blast, even if he's singing about being a "fish" or a "mule."
The Nelson Riddle Connection
You can't talk about this recording without mentioning Nelson Riddle. He was the architect of the Sinatra sound at Capitol and followed him over to Reprise. For Frank Sinatra Swinging on a Star, Riddle had a challenge: how do you make a song that is fundamentally "corny" sound cool?
He didn't overthink it.
The arrangement is lean. It’s not over-produced. It relies on Frank's phrasing—the way he hits the word "jar" or lingers on the "better off than you are." It’s a masterclass in how to handle "novelty" material without losing your dignity.
What the Critics Said (And Why They Were Wrong)
Some purists at the time thought Frank was slumming it. They wanted "In the Wee Small Hours" or "One for My Baby." They didn't want the Chairman singing about a pig who "doesn't care a feather which way he blows."
But they missed the point.
Sinatra was a storyteller. He treated the lyrics by Johnny Burke and the music by Jimmy Van Heusen with the same respect he gave a Gershwin ballad. He knew Van Heusen personally—they were drinking buddies and roommates. In fact, Jimmy Van Heusen wrote some of Sinatra's biggest hits, like "Come Fly with Me." There was a deep personal connection to this music that Bing Crosby just didn't have in the same way.
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Why People Get the Two Versions Confused
The Mandela Effect is real in the world of the Great American Songbook. Since both Bing and Frank are the "Kings of Croon," their catalogs often bleed together in the public imagination.
Bing’s version is the one you hear in the movie Going My Way. It’s got the choir. It’s very wholesome.
The Frank Sinatra Swinging on a Star version is the one you’d play at a cocktail party. It’s shorter, punchier, and lacks the "Sunday School" sincerity of the original. Frank’s version is essentially a tribute to his mentor and rival. It was a "hand-off" moment in music history—the younger lion finally acknowledging the older one’s territory, but marking it as his own.
The Technical Specs of the Session
If you’re a gearhead or a discography nerd, here are the nuts and bolts. The session took place at United Western Recorders in Los Angeles. This was the same room where The Beach Boys were tinkering with Pet Sounds just a couple of years later.
- Recording Date: January 28, 1964.
- Orchestra: Conducted by Nelson Riddle.
- Original Album: Days of Wine and Roses, Moon River and Other Academy Award Winners.
- Label: Reprise Records.
Interestingly, this wasn't just a one-off single. It was part of a focused effort to capture the "Gold Standard" of American songwriting before the British Invasion completely took over the charts.
Is the Sinatra Version Better?
That's the million-dollar question. "Better" is subjective, but "different" is a fact.
If you want the nostalgia of the 1940s, go with Bing. If you want the swagger of 1960s Vegas, the Frank Sinatra Swinging on a Star recording is your winner. Sinatra brings a certain irony to the lyrics. When he sings "you may grow up to be a pig," you can almost hear him winking at the microphone.
It's less about the moral of the story and more about the joy of the rhythm.
How to Listen to it Today
You won't find this on every "Greatest Hits" compilation. Usually, those are packed with "My Way" and "New York, New York." To find the high-quality version of Frank Sinatra Swinging on a Star, you need to look for the 2009 remastered version of the Academy Award Winners album.
The audio is crisp. You can hear the separation in the horns. Most importantly, you can hear Frank's breathing—the mark of a truly "human" recording that modern AI and auto-tune just can't replicate.
To truly appreciate the song, try listening to the Bing Crosby original and the Sinatra cover back-to-back. Notice the tempo. Notice the way the strings swell. You’ll see that Sinatra wasn't just copying a hit; he was translating a 1940s sentiment into a 1960s reality.
Check out the original 1964 Reprise vinyl pressings if you can find them. They have a warmth that digital files often lose, especially in the mid-range where Frank’s voice lives. Grab a copy of Days of Wine and Roses and listen to the whole record—it’s a snapshot of a legend at the absolute peak of his powers, having fun with the songs that built the industry.