Covering a song as beloved and iconic as “Fly Me To The Moon” is truly one of music’s riskiest endeavors. Certain songs loom so large in the cultural imagination that reinterpretations can feel unnecessary, or worse, pale imitations of the original. Yet every so often an artist approaches a classic not with the intent to replicate it, but to reveal something hidden within it. That’s exactly what Australian singer-songwriter Simon Orton accomplishes on this timeless track.

From the very first notes, it becomes clear that this is not an attempt to recreate the sophistication of Frank Sinatra’s legendary rendition. Simon Orton wisely takes a different path entirely. He slows the song down, strips away its big-band sheen, and transforms it into something remarkably intimate. Believe us when we say it’s a bold artistic choice, but one that pays off beautifully.

The greatest strength of this version has to be its restraint. Rather than overwhelming you with dramatic flourishes or ornate arrangements, Orton allows space to do much of the heavy lifting. At the center of it all though is Orton’s voice, which carries the weight of the entire performance with remarkable confidence. His vocals are rich and deeply expressive! There’s surely a warmth to his delivery that immediately draws you, but also an undercurrent of vulnerability that gives the performance its depth.

Interestingly, while Orton’s reinterpretation carries traces of country storytelling and warmth, it never fully settles into traditional country territory. Instead, it exists in a more timeless space, somewhere between folk intimacy, classic balladry, and understated Americana. That ambiguity works in the song’s favor, allowing the performance to feel universal rather than genre bound.

Reimagining a standard of this stature requires courage, but it also requires vision. Orton possesses both. He understands that the best covers don’t compete with the original, they converse with it. His rendition honors the legacy of the song while uncovering emotional layers that have always been there, waiting for someone to slow down long enough to find them.

“Fly Me To The Moon” has endured for generations because its message remains timeless. We’ve heard the original a thousand times, but because of him, we listened a little bit closer this time around and it really showed off some of the song’s subtleties. We urge you to give it a spin, so please, click those links below to listen in, follow along, and of course to stay tuned for more.

Listen to “Fly Me To The Moon”

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Simon Orton puts a new spin on Frank Sinatra's timeless “Fly Me To The Moon”