You know that feeling when you're flipping through a bin of CDs or scrolling through a digital library and you see that iconic, sepia-toned cover of Lenny Kravitz staring back at you? That’s the one. The Lenny Kravitz Greatest Hits album, released back in 2000, is basically the "gateway drug" to 90s rock and soul fusion. But honestly, most people treat it like a background playlist for a backyard BBQ without realizing how weird and risky it actually was at the time.
It’s easy to dismiss a "Best Of" collection as a corporate cash grab. For Lenny, though, this wasn't just a victory lap. It was a career-saving pivot.
The Record That Shouldn't Have Worked
By 1998, Lenny Kravitz was kinda hitting a wall. His 1995 album Circus was heavy, dark, and—to be blunt—didn’t move the needle like his earlier stuff. People were starting to write him off as a "retro" act who just copied Jimi Hendrix and John Lennon. Then he dropped 5.
That album changed everything because he finally embraced digital tech, Pro Tools, and synthesizers. When the Lenny Kravitz Greatest Hits compilation arrived two years later, it captured that specific moment where his old-school soul met his new-school electronic experimentation. It wasn't just a list of songs; it was proof that he had survived the 90s.
Why the tracklist is actually a mess (and why we love it)
If you look at the tracklist, it’s not chronological. It’s a sonic roller coaster. You go from the crunchy, 70s-style riff of "Are You Gonna Go My Way" straight into the polished, radio-ready sheen of "Fly Away."
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- "Again" was the brand new track for this release. It won him a Grammy. Think about that: a song added to a "hits" album became one of his biggest hits ever.
- "American Woman" wasn't even on the original version of the 5 album. It was a cover for the Austin Powers soundtrack that got so big they had to tack it onto the Greatest Hits.
- "It Ain't Over 'Til It's Over" sounds like it was recorded in 1972 at Motown, but it was 1991.
Most people don't realize that Lenny played almost every single instrument on these tracks. Drums, bass, guitar, keys—all him. He’s basically the Prince of rock and roll in that regard, but he rarely gets the credit for the sheer technicality of his studio work.
The "Derivative" Argument: Let's Get Real
Critics have spent thirty years calling Lenny a copycat. "He sounds too much like Led Zeppelin!" "He's just doing a Curtis Mayfield impression!"
Okay, sure. He wears his influences on his velvet sleeves. But there's a nuance here that the haters miss. In the early 90s, when everyone was wearing flannel and screaming about angst in Seattle, Lenny was out here wearing boas and singing about "Let Love Rule." He was a master synthesist. He took the analog warmth of the 60s and 70s and made it work for a generation that was starting to listen to techno.
The Lenny Kravitz Greatest Hits album sold over 10 million copies worldwide. You don't do those numbers just by being a "cover artist." You do them because people missed the feeling of a real guitar solo and a soulful falsetto.
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The Vinyl vs. Digital Dilemma
If you're a collector, the experience of this album changes depending on how you listen to it. The original CD and digital versions have a specific flow, but if you can find the double LP vinyl (the 180g Simply Vinyl pressing is the holy grail for some), the pacing feels different.
The bass on "Mr. Cab Driver" hits harder through a needle. The psych-rock ending of "Are You Gonna Go My Way" feels wider. It’s a tactile experience that matches the "vintage" ethos Lenny has chased his whole life.
What’s Missing?
No compilation is perfect. Fans usually grumble about the "deep cuts" that got left on the cutting room floor. Personally, I think "Is There Any Love in Your Heart" from the 1993 era deserved a spot over "Black Velveteen." "Black Velveteen" is cool, don't get me wrong—it's very Matrix-era industrial funk—but it doesn't have that raw, bleeding heart energy that defined Lenny's early career.
Also, if you're looking for his later work like "Dig In" or "California," you won't find them here. This collection stops right at the peak of his commercial powers in 2000.
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Actionable Tips for the Ultimate Listen
To really appreciate the Lenny Kravitz Greatest Hits, don't just shuffle it.
- Check the credits. Look up which songs he recorded in his home studio using vintage gear from the 60s. It changes how you hear the "fuzz" on the guitars.
- Compare the covers. Listen to "American Woman" by The Guess Who and then Lenny’s version. He took a classic rock staple and turned it into a gritty, sexy stomp.
- Watch the videos. The visual aesthetic of the "Again" video (directed by Paul Hunter) or "Are You Gonna Go My Way" (Mark Romanek) is inseparable from the music.
If you want to understand the bridge between classic rock and modern pop, this album is the blueprint. It’s not just a collection of radio songs; it’s a masterclass in how to stay relevant by looking backward while moving forward.
Start with "Always on the Run" for the Slash guitar feature, then move to "Believe" for the spiritual epicness. It’s a wild ride.