How to Reimagine a Classic Song (And Why You Should Try It)

There’s something magical about a great cover song—one that doesn’t just imitate the original but transforms it. A reimagined cover has the power to reveal hidden possibilities in the music, to shift its emotional core, or to shine a spotlight on a rhythmic, melodic, or harmonic element that might have gone unnoticed before.

One of my all-time favorite examples of this is Manfred Mann’s cover of Bruce Springsteen’s Blinded by the Light. It’s one of those rare cases where the reinterpretation takes the raw material and launches it into an entirely different realm—sonically, emotionally, and creatively. It’s more than a rendition—it’s a reinvention.

That’s what I love about doing covers: the chance to say something new with something old.

My Journey with “Autumn Leaves”

Recently, I revisited the classic Autumn Leaves—a tune with a seemingly infinite number of renditions already in existence. What could I possibly add to that conversation?

I found inspiration in a YouTube video where ten well-known guitarists each gave their take on the song. The video ran nearly an hour long, and the variety of approaches was staggering. But watching it sparked an important question for me: What would I do if I were asked to contribute a version for a channel like that?

I knew I couldn’t quite play like those guys—each had their own brilliant voice. But I thought, What’s my voice? That led me to a rhythmic concept I’d been exploring: modulating between straight 16th notes and swung 8th-note triplets.

It reminded me of the tune “We Got the Fu*k” by Horacio “El Negro” Hernández, with Robby Ameen on drums. In that song, the band modulates seamlessly between these two rhythmic feels, and I wanted to incorporate a similar approach into Autumn Leaves. So I crafted an arrangement with four bars of 4/4 in 16th-note subdivisions, followed by three bars of swung 4/4, where the subdivision becomes 8th-note triplets.

Here is my version of “Autumn Left.”

Building the Backing Track

The hardest part wasn’t the playing—it was building the backing track. I had to create a track at 100 BPM for the 16ths and then shift to a faster tempo—specifically 133.33 BPM—to match the feel of the triplets.

That meant some serious time-stretching to keep everything lined up. I chopped, matched, nudged, and stretched, alternating the tempo and subdivision in the track itself. Once it was done, though, it felt great to play over. I’d already practiced the rhythmic modulation, so improvising over it felt natural—musical, even.

Later, I even wrote a new tune called All Funked Up Blues that used the same rhythmic concept. I had hoped to try it live with my band Now from Brooklyn, but the piece was a little rhythmically complex, and since we hadn’t rehearsed it, we decided to save it for another time. I’m all about sending the material in advance, but if the band isn’t comfortable with it yet, it’s better not to force it.

Still, Autumn Leaves ended up getting some likes on YouTube and Instagram. More importantly, it taught me that reimagining a classic doesn’t have to mean going “bigger” or “fancier”—just more you.

Covering Jennifer Lopez (No, Seriously)

At another point, I was taking a course that emphasized building a following by covering trending songs. The idea was to anticipate what people would be searching for and be ready with a creative take. I saw that Jennifer Lopez had a movie coming out called Marry Me, with a title song of the same name. So I asked myself again: How could I make this artistically fulfilling for myself?

The answer: put it in 7/4.

That one decision opened up a whole new world for the arrangement. I mapped the melody onto the 7/4 time signature, creating a sort of rhythmic asymmetry that made the tune feel fresh. For the solo, I used my PRS CE guitar (which I no longer own—it always felt a bit too bright for my taste), and the whole thing ended up being a lot of fun to record.

It goes to show: whether you’re working with jazz standards or current pop hits, there’s always a way to inject your own artistry.

Here is my version of “On My Way (Marry Me)” by Jennifer Lopez.

Three Main Approaches to Reimagining Songs

From my experience—and from studying the greats—there are three main ways you can reimagine a song: rhythm, harmony, and melody.

1. Rhythmic Transformation

This is my go-to. Whether it’s subdividing differently, changing meter (as in 4/4 to 7/4), or playing with feel (straight vs. swing), rhythm has an incredible power to change how a song hits.

Think about how different Autumn Leaves feels with the rhythmic modulation I described. Or how Marry Me in 7/4 creates a sense of tension and release that wouldn’t be there in a conventional 4/4 groove.

Rhythmic transformations often require adjusting other elements—melody and harmony—to fit. But the result can be a completely new groove or mood.

2. Harmonic Reharmonization

Jazz musicians have long been masters of this. One great example is Herbie Hancock’s Possibilities album, where he brings jazz sensibility to pop tunes through harmonic innovation.

Reharmonization can be subtle—changing a few chords to reflect alternate emotional colors—or dramatic, replacing the original progression entirely. Either way, it can turn a simple song into something rich and complex.

One fun exercise is to take a tune you know well and try harmonizing it in a different mode or tonal center. What happens to the mood? The storytelling? The melodic choices?

3. Melodic Alteration

This includes changing the phrasing, ornamentation, or even tonal character of the melody. Singers do this all the time—think of how Billie Holiday rephrased melodies to reflect her own emotional world.

Or take the example of the Sound of Music classic “Do-Re-Mi” done in a minor key. I once heard a hilarious version of that, and it was striking how just changing the tonality made it feel like a completely different song—quirky, haunting, and funny all at once.

Melody can also be abstracted—sung or played over a vamp, stretched rhythmically, or even turned into a counterpoint line. There’s so much room to be inventive.

Other Creative Approaches

There are many more ways to personalize a cover:

• Change the lyrics (à la Weird Al)

• Strip it down to just voice and one instrument

• Mash it up with another song

• Change the genre entirely (ever heard a heavy metal Billie Jean?)

• Use unconventional instrumentation (ukulele, kora, cello, beatboxing, etc.)

• Loop and layer using modern production tools

Ultimately, the question becomes: What can I bring to this song that only I can bring?

Final Thoughts: Cover with a Purpose

Too often, cover songs are treated as filler, something to do when you don’t have your own material. But I believe they can be a creative goldmine—opportunities to connect, reinterpret, and grow.

When considering your own cover, ask yourself:

• What do I love about this song?

• What would make this feel artistically fulfilling to me?

• What can I bring out in this tune that others haven’t?

• What do I wish this song had that it doesn’t—and can I add it?

The possibilities are endless. That’s the beauty of music: it’s alive, and it keeps evolving through the hands, hearts, and imaginations of those who play it.

So don’t be afraid to dig into a classic. Flip it inside out. Warp the rhythm. Bend the harmony. Twist the melody. Or keep it simple—but deeply personal.

Make it yours.

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