He was a genius. A literal, multi-instrumental, one-man-studio-operation genius. But when you try to play the best of Prince, you realize pretty quickly that a "Best Of" collection is basically an impossible task. How do you cram a guy who wrote over 1,000 songs, played 27 instruments on his debut album, and switched genres faster than he changed silk suits into a single playlist? You don't. You can't.
Prince Rogers Nelson didn't make music for casual listening; he built a religion of funk, rock, and soul.
Honestly, most people start with Purple Rain. It's the obvious choice. It’s the safe choice. But if you stop there, you’re missing the gritty, DIY Minneapolis sound that defined the early 80s or the psychedelic sprawl of his later work with the New Power Generation. You've gotta dig deeper than the radio edits.
The Problem with "Greatest Hits" Mentality
Most streaming services will point you toward the 4Ever compilation or the Ultimate collection. These are fine. They’re "okay." But Prince hated the idea of his work being chopped up into bite-sized pieces for mass consumption. He was an album artist. To truly play the best of Prince, you have to understand the context of the eras.
Take the 1980 release Dirty Mind. It’s raw. It’s thin. It sounds like it was recorded in a basement because, well, it mostly was. Contrast that with the lush, over-produced (in a good way) layering of Diamonds and Pearls. If you just shuffle a hits list, the jump between the lo-fi funk of "Head" and the stadium pop of "Cream" is enough to give you whiplash.
The man lived in Paisley Park, a $10 million complex in Chanhassen, Minnesota, that acted as his sanctuary and his prison. He was constantly recording. There are thousands of tracks in "The Vault" that we are only just beginning to hear. When we talk about his "best," we are looking at a moving target that changes every time the estate releases a new "Super Deluxe" edition of a classic album.
The Warner Bros. War and the Name Change
You remember the "Artist Formerly Known as Prince" era, right? People laughed. They thought it was a gimmick. It wasn't. It was a desperate, legally fueled protest against a contract he felt made him a slave. During this time, he was releasing music at a breakneck pace just to get out of his deal.
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Some of his best work is buried in this era of "spite releases." Albums like The Gold Experience contain "The Most Beautiful Girl in the World," which is a masterpiece of melodic pop, yet it's often skipped because of the messy legal history surrounding that time period. To play the best of Prince means acknowledging the struggle he went through to own his masters. He was a pioneer in artist rights, long before it was trendy for pop stars to re-record their catalogs.
How to Actually Play the Best of Prince for a Real Vibe
If you're hosting a party or just sitting in your room with some high-end headphones, don't just hit "shuffle." You need a strategy. The Prince catalog is divided into distinct "flavors."
The Revolution Era (1984–1986)
This is the peak of the Minneapolis Sound. It’s synth-heavy, tight, and incredibly melodic. Think Around the World in a Day and Parade. This is where you find "Kiss" and "Raspberry Beret." It’s quirky. It’s psychedelic. It’s the sound of a band that was actually a band, not just Prince playing everything himself. Wendy Melvoin and Lisa Coleman added a sophisticated, Joni Mitchell-influenced texture that he never quite replicated after he fired them.
The Solo Mastery (1987)
Then comes Sign o' the Times. Ask any hardcore fan (a "Purple Yoda," as some call themselves), and they’ll tell you this is the actual best of Prince. It’s a double album that covers everything: social commentary, gender-bending identity, heartbreaking ballads, and the heaviest funk known to man. "Housequake" alone is worth the price of admission.
- 1999: The apocalyptic dance party.
- Controversy: The bridge between disco and the future.
- Lovesexy: The spiritual, weird, one-track-CD experiment.
- Musicology: The 2004 comeback that proved he still had the chops.
The Live Experience is Essential
You haven't really heard Prince until you've heard him live. The studio versions were often just the blueprints. On stage, he was a guitar god. People forget that. He was arguably on the same level as Jimi Hendrix or Eddie Van Halen.
Watch the 2004 Rock and Roll Hall of Fame performance of "While My Guitar Gently Weeps." He shows up, melts everyone's faces with a solo that defies physics, and then tosses his guitar into the air where it seemingly disappears. That’s Prince. If you want to play the best of Prince, you need to find the live recordings from the Lovesexy tour or the One Nite Alone acoustic sets. The intimacy he could command in a room of 10,000 people was spooky.
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Why the B-Sides Often Win
Prince was so prolific that his "throwaway" tracks were better than most people's lead singles. "Erotic City" was a B-side. "17 Days" was a B-side. "How Come U Don't Call Me Anymore?" was a B-side.
There is a depth to the catalog that rewards the "deep diver." If you only stay on the surface with "Little Red Corvette," you’re getting the polished, radio-ready version of a man who was actually much weirder and more interesting than the Top 40 charts allowed him to be. He challenged everything: religion, sex, race, and the music industry itself.
He was a vegetarian who didn't swear in his later years due to his faith as a Jehovah’s Witness, yet he wrote some of the most provocative lyrics in the history of the Billboard 100. That duality is why we are still talking about him. He was a walking contradiction wrapped in purple lace.
The Sonic Architecture of Paisley Park
When you listen to a Prince track, listen for the "space." Unlike modern pop that is compressed to death, Prince let his songs breathe. He often stripped out the bass entirely—look at "When Doves Cry." It’s a revolutionary move. A funk song with no bass guitar? It shouldn't work. But because it was Prince, it became the biggest song of 1984.
He used the Linn LM-1 drum machine like a lead instrument. He detuned it, ran it through guitar pedals, and created a signature "knock" that identified a Prince track within three seconds. That technical innovation is part of why his music doesn't age the way other 80s productions do. It sounds like it’s from the future, even forty years later.
Actionable Steps for the Ultimate Prince Sessions
To truly appreciate the scope of his work, move beyond the standard hits and follow this progression to build your own definitive collection.
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1. Start with the "Big Three" Albums
Don't just buy a hits disc. Listen to 1999, Purple Rain, and Sign o' the Times in their entirety. These three records represent the holy trinity of his creative output. They show his transition from a synth-pop innovator to a global superstar and finally to a visionary auteur.
2. Hunt for the Extended Versions
Prince was a master of the 12-inch remix. In the 80s, these weren't just dance beats added to a song; they were entirely new movements. The 10-minute version of "I Would Die 4 U" or the extended "Mountains" are essential listening. They show the improvisational "jam band" side of his personality.
3. Explore the Side Projects
Prince wrote and produced hits for other people that he never took credit for on the cover. The Time's 777-9311, Sheena Easton’s "Sugar Walls," and The Bangles' "Manic Monday" are all Prince songs. Playing the best of Prince involves recognizing his DNA in the entire 1980s pop landscape.
4. Check out the Aftershows
The "real" Prince fans know that the concert wasn't over when the arena emptied. He would go to a small club at 2:00 AM and play for another three hours. Bootlegs of these aftershows are legendary. They feature him playing jazz, blues, and deep funk covers that he never touched in his main sets.
5. Visit the Vault Releases
Since his passing in 2016, the estate has been curated by people who actually care about the legacy. The Originals album, which features Prince’s own versions of songs he gave to others, is a must-hear. It’s fascinating to hear him sing "Nothing Compares 2 U" and realize how much of the "Sinead O'Connor sound" was actually just Prince's demo.
Music is subjective, but Prince is an objective standard of excellence. Whether you’re into the leather-jacket-and-motorcycle vibe of his early days or the refined, orchestral arrangements of his final years, there is something in the catalog that will stick. Just remember: it’s a marathon, not a sprint. You don't "finish" listening to Prince. You just find new layers every time you press play.