Prince – Timeless: Ten Songs, Five Decades and One Big Question: Who Is This For?
Lifelong Prince obsessive, Vault trainspotter and the kind of fan who got his Prince tattoo on April 21, 2016, the very day Prince died. For Timeless, Ben goes track by track through five decades of unreleased Prince, placing every song in its era and asking the question the Estate still hasn’t entirely answered: who is this actually for?
Prince,Timeless: Ten Songs, Five Decades and One Big Question: Who Is This For?
Ten years.
It still feels faintly ridiculous writing that.
Ten years since Prince walked into whatever comes next, leaving behind one of the most extraordinary recorded legacies in popular music and, somewhere inside Paisley Park and its associated archives, enough unreleased music to keep those of us afflicted with this particular purple disease occupied for the rest of our natural lives.
So you might have expected 2026 to be enormous.
Not grotesque. Not exploitative. Nobody needs Prince-branded breakfast cereal and a hologram residency at the Sphere. But significant. Thoughtful. A year in which the people now charged with protecting his work reminded the world, particularly a world increasingly discovering twentieth-century artists through algorithms, television syncs and thirty-second clips, just what we lost on April 21, 2016.
Instead, after several frustratingly quiet years, we haveTimeless. And I have questions.
The frustration among Prince fans hasn't exactly materialised from nowhere. Prince'Timeless is the first collection of previously unheard recordings since 2023. Indeed, 2024 and 2025 became the first two consecutive full calendar years since Prince died without an album containing newly released Vault recordings. There were mitigating circumstances, including the protracted Netflix documentary dispute and its complicated relationship with access to Vault material, but fans don't experience contractual gridlock. They experience silence.
Then came Timeless, released on August 28, ten tracks spanning 1977 to 2016, deliberately chosen to represent five decades of Prince's creative life. Estate co-manager L. Londell McMillan has essentially described the concept as ten unreleased recordings for the tenth anniversary, while arguing that a concise release is easier for younger listeners to approach than another enormous, expensive Super Deluxe box. Fair enough.
Except...
Who is Timeless actually for?
Is some Prince-curious 22-year-old who has just heard ‘Purple Rain’ in Stranger Things really going to begin their journey with an unreleased 1977 recording, an abandoned 1985 song, a demo Prince eventually gave Céline Dion, an obscure 2003 funk workout and a live B-side from 2016?
Of course not.
They’ll (hopefully) start with Purple Rain. Or ‘Kiss’. Or ‘1999’. Or Sign O’ The Times. Or a playlist. And they should.
Timeless is for us tragics. The trainspotters. The people who see 1981, Kiowa Trail Home Studio in the liner notes and immediately sit upright. And that’s perfectly fine. Just call it what it is.
Because Timeless isn’t really a new Prince album. Prince didn’t conceive it, sequence it or choose these songs to speak to one another. It’s an archival compilation and it plays accordingly, with no real thematic through-line beyond the fact that the songs run chronologically through his career.
With ‘With This Tear’ and ‘Stone’ released in advance, both good songs but hardly mind-blowing revelations, my apprehensions were high. The awful artwork and clichéd title didn’t help matters. Nor did seeing ‘Tick Tick Bang’ and a live version of ‘How Come U Don’t Call Me Anymore?’ on the tracklist do much to raise my confidence. Neither title was exactly new to us. One is a live rendition of a B-side, albeit one of my favourite Prince songs, while the other had already been officially released in a very different form. Several of the other titles had also circulated among fans for years on unofficial bootlegs.
So, yes, I went in wary.
But here we are, a week later, and I’ve barely played anything else. I’ve absolutely rinsed Timeless, and it needs to be admitted: this is an extraordinarily intriguing ten-stop tour through Prince’s working life. Once you accept it on those terms, rather than expecting some great lost Prince album to suddenly reveal itself, it becomes much easier to enjoy.
And there is plenty here for a Prince obsessive to enjoy, so let’s journey through the tracks rather than judge Timeless as a conventional album, because that's where the real intrigue lies. There is some real gold in here.
1. ‘I Am You’
1977: Before For You. Before everything.
We begin almost absurdly early and here lies the compilation's greatest revelation. ‘I Am You’ was recorded at Sound 80 in Minneapolis in March 1977, when Prince was still a teenager and before the release of For You. David Rivkin engineered the session and Prince handles the instruments and vocals. Fascinatingly, the song isn't known to have appeared on a configuration of For You, although Prince later performed it during his first proper solo concerts at Minneapolis' Capri Theatre on January 7, 1979 (fun fact - the day this scribe and #1 Prince fan was born).
This is why Timeless immediately works on me despite all my reservations. You're not simply hearing another Prince song. You're hearing Prince becoming Prince. All the ingredients haven't completely fused yet, but they're sitting there on the bench. The rhythmic obsession. The falsetto. The slightly filthy little guitar movements. The confidence that seems ludicrous coming from someone so young.
There are even musical ideas here that would later resurface in music associated with The Time.
If U Dig: ‘Soft and Wet’, 'I Wanna Be Your Lover', 'Lady Cab Driver'
2. ‘Tick Tick Bang’
1981: This is Controversy Prince, still sharpening the knife
We skip the Prince and Dirty Mind eras, but NOW we’re cooking. This is not the ‘Tick, Tick, Bang’ most people know from 1990’s Graffiti Bridge. This is its younger, nastier ancestor. It begins with an otherworldly 1-2-3-4 scream and rips straight into something moving at breakneck speed, almost, dare I say it, metal.
Prince originally recorded the song in the spring or summer of 1981 at his Kiowa Trail home studio, during the same session as ‘Controversy’ and the unreleased ‘Poppa Grooves’. Nearly a decade later, he went back to it and re-recorded the song from scratch for Graffiti Bridge, with mostly new lyrics and a much more hip-hop-inflected feel.
And the distinction matters.
This belongs to that thrilling moment when Prince had stopped merely being precociously talented and started becoming dangerous.
Dirty Mind had blown the doors off. Controversy was taking sex, race, religion, identity and technology and feeding them through one skinny man’s increasingly alien understanding of funk and rock.
This ‘Tick Tick Bang’ sounds like it belongs right there in that room.
For collectors who have known versions of this material through bootlegs and murky files for years, hearing an official release is itself part of the thrill. This is precisely the kind of excavation the Vault should be doing.
If U dig: ‘Controversy’, ‘Bambi’ and ‘Let’s Pretend We’re Married’
3. ‘Heaven’
1985: Prince walks out of Purple Rain and refuses to stay there
We skip Purple Rain and land on May 26, 1985. Sunset Sound, Studio 3. And that date alone places ‘Heaven’ in one of the most fascinating periods of Prince’s entire career. The Purple Rain tour had ended less than two months earlier, on April 7. Around The World In A Day had then arrived on April 22, barely two weeks later, while work on what would become Parade had already begun that very same month. The rest of the planet was still trying to process what Prince had just done and Prince, being Prince and much to his team's dismay, was already several moves ahead.
Into that ridiculous burst of activity comes ‘Heaven’.
Prince recorded, overdubbed and mixed the song at Sunset Sound on May 26, handling all the vocals and instruments himself. And it wasn’t the only thing occupying him that day. He also recorded the still-unreleased ‘Come Elektra Tuesday’, featuring Jill Jones on backing vocals, while ‘Hello’, the wonderfully pissed-off response to the controversy surrounding ‘We Are The World’, had been recorded just two days earlier and was being worked on again on the 26th.
That’s the context in which you need to hear ‘Heaven’: not as some isolated song Prince tossed into the Vault, but as another piece flying off the machine while the machine was operating at frankly ludicrous speed.
And musically, you can hear why this period remains such a rabbit hole for Prince obsessives. The psychedelic colours of Around The World In A Day are still swirling around, but there’s also something more nocturnal and hypnotic creeping in. You can hear Prince moving towards Parade and, beyond that, the extraordinary creative free-for-all that would eventually produce Dream Factory, Crystal Ball, Camille and Sign O’ The Times. Except Prince wasn’t finished with ‘Heaven’.
More than a year later, in November 1986, Susannah Melvoin added vocals to the track, either at Sunset Sound or Prince’s Galpin Boulevard home studio. Even the precise location remains uncertain. By then The Revolution was effectively over and Prince’s life, band and music had shifted again completely.
The song was subsequently considered for The Dawn, one of those great abandoned Prince projects that could swallow an obsessive for an afternoon. The proposed musical or film was never completed and its exact shape remains murky, but songs associated with it included ‘All My Dreams’, ‘Others Here With Us’, ‘God Is Everywhere’, ‘Crucial’, ‘The Cocoa Boys’ and ‘When The Dawn Of The Morning Comes’.
Just look at those titles.
Yo, Estate - give me that bloody album!!
There’s another treat here for those of us who have lived with bootlegs for years. The 4:29 version finally released on Timeless isn’t the only ‘Heaven’ sitting in the Vault. A longer version also exists without Susannah’s later backing vocals, meaning the song itself provides a neat little example of how Prince would return to an idea, reshape it and then potentially pull it into an entirely different project more than a year after first recording it.
And, remarkably, ‘Heaven’ is not believed to have ever been performed live. So what we have on Timeless is effectively a snapshot of something that Prince kept circling but never allowed out into the world.
That makes it fascinating before you’ve even decided whether it’s a masterpiece.
This is the Prince era I could happily have an entire Vault release devoted to: Around The World In A Day bleeding into Parade, The Revolution mutating, Wendy and Lisa stretching his musical vocabulary, Susannah entering the emotional landscape and Dream Factory somewhere over the horizon.
A whole universe.
And Timeless gives us one postcard from it.
That’s both wonderful and maddening.
If U dig: ‘Erotic City’, ‘Joy In Repetition’ and ‘Paisley Park’
4. ‘I Wonder’
1989: Somewhere between Batman and the next reinvention
Now here’s a real highlight. ‘I Wonder’ is a wide-eyed love song seemingly full of joy, Prince wondering aloud whether the woman occupying his thoughts knows just how deeply he feels about her. It’s immediate, melodic and ridiculously easy to fall for.
Which raises an obvious question: why wouldn’t our beloved Estate have led with something like this?
It could’ve been a moment.
‘I Wonder’ was recorded at Paisley Park on August 5, 1989, with Prince handling all the vocals and instruments himself. Think about where he was. Batman had been released only weeks earlier and was sitting at the centre of pop culture. Lovesexy and its enormous tour were behind him. Graffiti Bridge was beginning to take shape. The Revolution was long gone, but the New Power Generation didn’t yet exist in the form we’d come to know.
And given Prince’s romantic involvement with Batman star Kim Basinger around this period, it’s certainly tempting to wonder whether she might be the object of all this affection.
Prince was between worlds again.
And ‘I Wonder’ seems to suit that position beautifully. It doesn’t scream Batman, it's too light hearted. Nor does it quite sound like the NPG-heavy Prince who would emerge with Diamonds And Pearls a couple of years later. It’s Prince floating between the two, still essentially doing everything himself, with this wonderfully buoyant mid-tempo groove, stacked vocals and an almost disarmingly straightforward romanticism. At points, it almost feels like Prince wandered into a Disney soundtrack.
Then, because this is Prince, the story gets complicated. Additional work was done on ‘I Wonder’ in late 1991 or 1992 at Paisley Park, adding to a song that had already been sitting around for a couple of years. A sparser early version is also known to exist, while the later version was retitled ‘Wonder’.
And here comes one of those wonderfully nerdy disputes that Prince’s Vault seems destined to produce forever. The official Timeless campaign dates the released track to 1989, and current Prince Vault documentation identifies the 4:11 version on the album as the original 1989 recording. Yet some longtime collectors familiar with the earlier bootlegged version hear keyboards, piano and percussion associated with the later 1991–92 work on what has now been released. In other words, even among the people who have been trading this stuff for decades, exactly which stage of ‘I Wonder’ we’ve finally been handed is being debated.
Welcome to Prince fandom.
What we do know is that Prince never completely forgot about the song. In June 2000, during Prince: A Celebration at Paisley Park, visitors were presented with computer screens containing titles from the Vault and invited to vote for songs they wanted included on a proposed Crystal Ball Volume II. ‘I Wonder’, by then listed as ‘Wonder’, was among the selections.
Fans chose it.
Crystal Ball Volume II never came out.
So the song disappeared back into the Vault. Again.
It’s not believed that Prince ever performed ‘I Wonder’ live either, making its paper trail even stranger. A song this warm, accessible and apparently fully formed survived multiple rounds of studio work, was remembered by Prince more than a decade after he first recorded it, was actively chosen by his fans for release, and still somehow remained officially unheard during his lifetime.
Twenty-six years after that Crystal Ball II vote, here it finally is.
This is the stuff that makes Prince fandom feel faintly archaeological. A title appears on a list. Then a bootleg. Then another version. Then a rumour. Then an abandoned compilation. Decades pass.
Eventually, the song walks through the front door.
And in the case of ‘I Wonder’, you’re left wondering why it took so bloody long. It's that good!
If U dig: ‘Starfish & Coffee’, ‘Elephants & Flowers’ and ‘I Wish U Heaven’
5. ‘With This Tear’
1991: Diamonds And Pearls, the NPG and a song destined for Céline Dion
I understand why people love this, but it’s not where my Prince pleasure-centre lights up. I’ve never been particularly drawn to the oversentimental ballads, unless we’re talking ‘Diamonds And Pearls’, which somehow gets a permanent exemption.
This one already has mythology attached. Prince recorded ‘With This Tear’ at Paisley Park on November 19, 1991, only weeks after Diamonds And Pearls was released. Clare Fischer subsequently arranged the orchestration, giving it the sort of sweeping, unapologetically romantic grandeur that makes its eventual destination feel almost inevitable.
The song appears to have first been intended for Jevetta Steele before Prince ultimately gave it to Céline Dion. Her version appeared on her 1992 self-titled album, with Prince credited as writer and producer.
And for decades, that’s essentially how the wider world knew ‘With This Tear’.
Now, finally, we get Prince.
Perhaps this is exactly the sort of thing that should have appeared on 2019’s Originals, or better yet, a sequel. Because what interests me about ‘With This Tear’ isn’t simply the novelty of hearing Prince sing a song we associate with Céline Dion. It’s hearing the enormous stylistic distance between what another artist could make of a Prince composition and the strange emotional architecture contained in Prince’s own version. You can suddenly hear the DNA.
I admire it more than I love it. It’s beautifully constructed, Prince sounds terrific and Clare Fischer’s orchestration gives it enormous emotional weight. But if I’m reaching for Prince at his most romantic, there are quite a few songs I’m putting on first.
If U dig: ‘Diamonds And Pearls’, ‘Nothing Compares 2 U’ and ‘Adore’
6. ‘Stone’
1995: The Artist, Warner Bros. and the road toward Emancipation
A real grower, this one.
By 1995, we are nowhere near the Prince who opened Timeless.
He has become the symbol.
‘SLAVE’ has appeared on his face.
The relationship with Warner Bros. is poisoned.
The Gold Experience exists but is still caught in the machinery of that fight, sitting unreleased while Prince continues making music at a rate that must have terrified everyone tasked with trying to sell it.
And he is recording at a ludicrous pace.
‘Stone’ has an especially interesting origin. It began life as ‘Nothing Left To Give’, one of a group of songs songwriter and vocalist Sandra St. Victor sent to Prince in the spring of 1995 after the pair agreed to explore working together. Prince took her material, added lyrics and music of his own and recorded his version at Paisley Park on April 30, 1995.
Kirk Johnson, soon to become an increasingly important presence in Prince’s musical world, is credited with drums and percussion programming, while Prince handles the rest.
And here’s where the Prince archaeology gets particularly good.
‘Stone’ didn’t immediately disappear into the Vault. It was placed on Playtime By Versace, a wonderfully obscure 1995 project compiled from Prince’s rapidly expanding pile of new material. The collection included tracks such as ‘Soul Sanctuary’, ‘I Like It There’, ‘Dinner With Delores’, ‘Van Gogh’ and ‘I’ll Never B Another Fool’, and appears to have been conceived as a special art-and-music gift connected with Gianni and Donatella Versace rather than a conventional commercial Prince album.
Even the artwork survives.
Of course it does.
‘Stone’ then refused to die.
By March or April 1996 it had made its way onto a configuration of Emancipation, sitting as track four on disc three, track 26 overall. That is wonderfully specific evidence that Prince still saw something in it nearly a year after recording it.
And then it vanished again.
When Emancipation finally arrived in November 1996, ‘Stone’ was nowhere to be found. Sandra St. Victor eventually released her own original ‘Nothing Left To Give’ in 2018 as part of Sanctuary, which means we can now hear the seed Prince started with and just how thoroughly he Prince-ified it.
And musically, ‘Stone’ raises another possibility about why it might have remained on the cutting-room floor. Because tell me you don’t hear ‘Cream’.
That cowbell. That same lazy, sexy, mid-tempo strut is all over it. Prince sits slightly behind the groove, letting the bass and programmed drums do the walking while his vocal practically smirks over the top.
And perhaps that was part of the problem.
Prince had already made ‘Cream’.
A much better ‘Cream’.
That doesn’t make ‘Stone’ a failure. Quite the opposite. After initially leaving me fairly unmoved when it arrived as an advance track, this thing has grown enormously with repeated plays. But you can also imagine Prince listening back and deciding he had already perfected this particular shade of swagger a few years earlier.
That may be pure speculation, of course. Prince never left us a note saying, “too much like ‘Cream’, chuck it in the Vault”. But sometimes hearing the unreleased material helps explain the choices almost as much as it reveals what we missed.
And zoom out from the song for a moment and ‘Stone’ becomes something more interesting still.
Prince was making records faster than Warner could release them, changing his name, fighting publicly for ownership and freedom, assembling and abandoning projects, feeding songs to other artists, stockpiling music and already moving towards the moment when he could finally declare himself emancipated. ‘Stone’ isn’t merely a Vault curiosity. It’s debris from the explosion.
If U dig: ‘Cream’
7. ‘Calabama’
2003: Between the wilderness years and Musicology
A kinda wonderful horn-driven jam, an old school joint 4 the true funk soldiers with Prince rapping like it’s still 1995 and that angsty spike from the Warner wars hasn’t completely left his throat. There’s something wonderfully belligerent about it, but also something much looser and funkier beginning to emerge. You can almost hear the road towards the great mainstream return of Musicology opening up in front of him.
And then things get complicated.
‘Calabama’ was recorded at Paisley Park on January 21, 2003, with John Blackwell on drums, during that fascinating period between the adventurous The Rainbow Children / One Nite Alone... world and Prince’s re-emergence into the wider pop-cultural conversation with Musicology the following year. Intriguingly, Calabama may have been more than just a song.
At the 2024 Celebration at Paisley Park, the track was reportedly played during a Vault listening session and described as the title track of an album Prince had been developing before Musicology. Almost nothing else is known about the project. No sequence has surfaced. No definitive list of songs. Just the tantalising suggestion that somewhere in Prince’s impossibly tangled 2003 output there was another album taking shape.
There’s also another little piece of connective tissue buried inside the track: towards the end, ‘Calabama’ moves into a rap drawing from the previously recorded ‘Prince And The Band’.
Exactly the sort of fragment Vault obsessives live for.
Except the version of ‘Calabama’ released on Timeless also presents the Estate with its biggest problem.
Because at least some of the horns we are hearing were not recorded while Prince was alive.
The album credits list former NPG trombonist Greg Boyer alongside Adrian Crutchfield and Lynn Grissett. That alone raised eyebrows among serious Prince trainspotters: Crutchfield and Grissett aren’t known to have begun working with Prince until 2012, almost a decade after ‘Calabama’ was recorded.
Then Greg Boyer revealed that his own horn contribution had actually been recorded only several months before the release of Timeless.
In 2026.
Ten years after Prince died.
And it gets worse.
Estate co-chair Charles Spicer had previously stated that nothing had been added to ‘Calabama’. After Boyer’s revelation, Spicer publicly corrected himself, acknowledging that the released version does contain additional horns and taking responsibility for his earlier statement.
And I’m sorry, but that matters enormously.
Mix Prince’s multitracks? Of course.
Restore them? Absolutely.
Master them properly? Please.
But adding newly recorded instrumentation to a Prince recording ten years after Prince died crosses into entirely different territory.
Maybe the horns improve ‘Calabama’.
They probably do.
That’s almost irrelevant.
Prince was one of the most famously controlling recording artists who ever lived. He could obsess over a drum sound, change a bass part, remove an entire musician, rebuild a track overnight or scrap a finished record because something no longer felt right to him.
Arrangement wasn’t decoration.
Arrangement was composition.
So if somebody is going to add new musical performances to an archival Prince recording after his death, we need to know.
Clearly.
On the sleeve.
Not after a musician casually reveals it on Facebook four days after the album comes out.
Better still, give us both versions. Give us Prince’s 2003 recording as he left it, then, if there is genuine historical justification for completing or augmenting something, present that separately and explain exactly what was done and why.
Because once you start quietly “finishing” Prince recordings, where exactly is the line?
A horn overdub?
A guitar part?
Backing vocals?
A new drum track?
At what point does an unreleased Prince recording stop being an archival document and start becoming somebody else’s interpretation of what Prince might have wanted?
That’s dangerous territory.
The Vault should preserve Prince’s decisions, including the strange ones, the unfinished ones and even the ones we might think we can improve.
Especially those.
Which makes ‘Calabama’ a strange contradiction. Musically, it’s one of the most enjoyable discoveries on Timeless, a funky, horn-soaked little monster that makes me wish we knew infinitely more about this mysterious abandoned 2003 project.
But historically, it may also become the song Timeless is remembered for.
And not for the reason the Estate would have wanted.
If U dig: ‘Musicology’, ‘Sexy MF’ and ‘Days of Wild’
8. ‘The Guilty Ones’
2007: The 21 Nights machine still operating at full throttle
He loves you, baby, but not like he loves his guitar.
It’s October 26, 2007. Prince had only just come off those extraordinary 21 nights at London’s O2 Arena and the energy here is palpable.
‘The Guilty Ones’ is a ferocious slice of guitar-led funk-rock, all muscular rhythm section, stabbing guitar and Prince seemingly delighted to remind everybody that, yes, he could still absolutely crush you with six strings whenever he felt like it. There’s some ‘Fury’ in its teeth, some ‘Peach’ in its strut and plenty of the harder rock attack he’d just unleashed on ‘Guitar’.
And listen to that band.
Prince recorded ‘The Guilty Ones’ at Paisley Park with Cora Coleman-Dunham on drums, Josh Dunham on bass and Marva King and Shelby J. on backing vocals, with Ian Boxill engineering the session. Prince, naturally, produced, arranged, composed and performed everything else.
This wasn’t some randomly assembled studio crew either. These were musicians who had just been helping Prince tear through London.
His record-breaking O2 residency had run from August 1 to September 21, selling out all 21 shows, with plenty of legendary late-night aftershows at the nearby IndigO2 thrown in for good measure. Prince then played another aftershow in the early hours of September 22 before leaving London. Barely five weeks later, he was back at Paisley Park recording ‘The Guilty Ones’.
No wonder it sounds like a band that hasn’t cooled down yet.
And there’s a lovely little historical breadcrumb here too. Prince clearly didn’t completely forget the song after putting it away. Portions of its lyrics subsequently resurfaced in 21 Nights, the lavish photography book documenting that London residency, published the following year. At the time, of course, readers weren’t told they were looking at words from an unreleased song called ‘The Guilty Ones’.
Another Prince clue hiding in plain sight for nearly two decades.
There’s something almost self-mythologising about the song too. Prince sings of proving that he is still the master, with guitar and drums as the evidence, which feels especially pointed coming at this moment in his career.
Because 2007 Prince had very little left to prove.
He’d already engineered his huge Musicology comeback. 3121 had become his first US number one album since Batman. Planet Earth had arrived that July, including the appropriately titled ‘Guitar’, and Prince had then marched into a brand-new London arena and sold it out 21 bloody times.
The supposedly difficult, commercially wayward artist of the late ’90s and early 2000s was now a colossal live attraction again.
Which brings us back to one of the reasons the chronological idea behind Timeless actually works.
Listen to where we’ve travelled.
The 18-year-old making virtually everything himself in 1977 has become this extraordinary bandleader three decades later. Prince was still capable of playing nearly anything you put in front of him, but by this stage he also knew precisely how to assemble a band that could turn on his signals instantaneously.
And ‘The Guilty Ones’ captures that beautifully.
It isn’t necessarily some missing cornerstone of the Prince catalogue, but it absolutely sounds like a photograph of Prince in 2007: confident, combative, guitar in hand and surrounded by musicians capable of following him wherever he decided to go.
This is late-period Prince before anybody thought of him as late-period Prince.
If U dig: ‘Fury’, ‘Peach’ and ‘Guitar’
9. ‘Bestest Friend’
2012: The last great reinvention begins stirring
Now this is what I want from the Vault. ‘Bestest Friend’ was recorded at Paisley Park on September 3, 2012, and unlike several of the songs we’ve already encountered on Timeless, this one didn’t arrive trailing decades of bootlegs, fan mythology and alternate versions behind it.
For most of us, this really is a new Prince song.
And what a strange, beautiful thing it is.
A lush, bittersweet slice of late-period soul, ‘Bestest Friend’ finds Prince singing about a relationship that has gone badly wrong, addressing someone who was once his closest companion, his “perfect blend”, but has now left him wounded and betrayed. The music, meanwhile, is almost perversely gorgeous: mellow electric piano, sweeping horns, falsetto and that familiar Prince trick of wrapping emotional damage in something sumptuous.
Prince handles the vocals and instruments, but the NPG Hornz give the track much of its character: Michael B. Nelson on trombone, Kathy Jensen and Kenni Holmen on saxophones, Dave Jensen and Steve Strand on trumpets.
And there’s a neat connection to Timeless itself. The engineer sitting behind the desk at Paisley Park that day was Chris James, who worked with Prince during this later period and would go on to contribute to Plectrumelectrum, Art Official Age and HITnRUN Phase Two. Fourteen years later, James is the man the Estate brought back to mix and master Timeless.
So on ‘Bestest Friend’, at least, there’s a reassuring continuity: the person presenting this recording to us in 2026 was actually there when Prince made it. And September 2012 is another fascinating little hinge in Prince history.
We’re just months away from 3RDEYEGIRL beginning to take shape and the renewed late-career creative sprint that would eventually give us Plectrumelectrum, Art Official Age, HITnRUN Phase One and HITnRUN Phase Two. Prince was about to re-embrace the guitar with Donna Grantis, Hannah Welton and Ida Nielsen, start experimenting with Twitter and guerrilla releases, sign another major-label deal and generally become wonderfully difficult to predict all over again.
Yet ‘Bestest Friend’ doesn’t really point towards the garage-rock crunch of 3RDEYEGIRL.
Instead, it reminds you that Prince never moved neatly from one style to another. Even while one musical personality was beginning to form, another could be sitting at Paisley Park making this huge, sophisticated, horn-drenched soul ballad.
And then there’s the song’s relative obscurity.
Unlike ‘Heaven’, ‘I Wonder’ or ‘Tick Tick Bang’, this wasn’t one of those titles Prince collectors had been staring at on bootleg tracklists since the days of dial-up internet. There wasn’t some legendary seven-minute version everybody had already mentally canonised.
It simply turns up.
Fourteen years after it was recorded.
Fully formed.
And that’s exactly what I want from the Vault.
Not simply better-sounding versions of things Prince obsessives have already owned in dubious quality for thirty years.
Surprise me.
Give me the songs we didn’t even know enough to ask for.
Show me rooms in Paisley Park I didn’t know existed.
‘Bestest Friend’ does exactly that.
If U dig: ‘Future Soul Song’, ‘The Beautiful Ones’ and ‘Breakdown’
10. ‘How Come U Don’t Call Me Anymore?’ (Live)
2016: The final tour
And then there is this, one of the least interesting inclusions is head and shoulders the finest. March 4, 2016. Oracle Arena, Oakland. Prince alone at the piano on the Piano & A Microphone tour, just weeks after I had watched him play four of these extraordinary shows myself, and only weeks before he would be gone.
And he’s playing one of my favourite Prince songs.
‘How Come U Don’t Call Me Anymore?’ had first appeared way back in 1982 as the B-side to ‘1999’, one of those ridiculous Prince B-sides that would constitute a career highlight for most other artists. Alicia Keys then carried it to another generation, recording her own version for Songs In A Minor in 2001 and releasing it as a single the following year.
But Prince never really let the song go either.
He performed it regularly on the 1999 and Purple Rain tours, returned to it throughout the ’90s, made it a fixture of the One Nite Alone... shows in 2002 and was still singing it on Piano & A Microphone in 2016.
An official live version from Portland in 2002 had already appeared on One Nite Alone... Live!, while another performance from the legendary 1985 Syracuse show would eventually be released as part of Prince And The Revolution: Live.
So yes, seeing another live ‘How Come U Don’t Call Me Anymore?’ sitting at the end of a supposed album of Vault discoveries initially felt peculiar.
We know this song.
We already have live versions.
Why is it here?
Then you hear it.
The Timeless performance runs 5:54 and is Prince sitting alone at the piano and doing what he had always done with this song: pulling it apart, stretching the silences, changing the phrasing, moving from wounded vulnerability to gospel testifying and back again. There is no band to hide behind and absolutely nowhere for the emotion to go.
And now, of course, it is impossible to hear without knowing what comes next.
Six weeks later, Prince was dead.
This was not his final performance of ‘How Come U Don’t Call Me Anymore?’. He would return to it at his final full concert, the second show at Atlanta’s Fox Theatre on April 14. In fact, he had attempted it during the first Atlanta performance that night before abandoning it, then came back and played it properly during the second.
That second concert became Prince’s final full show.
Three days later, he appeared briefly at Paisley Park and played two songs at the piano during a party.
Four days after that, he was gone.
Knowing all of that gives the Oakland recording a weight it obviously did not possess when Prince performed it.
But I don’t want to turn every note he played in 2016 into prophecy.
That does him a disservice too.
Because what you actually hear on ‘How Come U Don’t Call Me Anymore?’ is not a man delivering some conscious farewell. You hear Prince doing what he had been doing for more than three decades: taking a song he knew intimately and finding another way inside it.
And that may be why it ultimately earns its strange place at the end of Timeless.
As sequencing, it is still peculiar.
Nine studio Vault recordings followed by one live performance of a song we’ve known since 1982.
Again, album?
Not really.
But as the final stop on this chronological journey, there is something quietly devastating about Prince reaching all the way back to the beginning of his imperial period, sitting at a piano in 2016 and discovering that the song can still tell him something.
We began Timeless with an 18-year-old Prince in 1977, playing everything himself and still figuring out exactly what Prince music might become.
Thirty-nine years later, almost everything has changed.
The fame. The bands. The clothes. The labels. The name. The fights. The lovers. The studios. The technology. The entire bloody music industry.
Strip it all away and here he is again.
One man.
One instrument.
One song.
The young man from track one is still in there.
And perhaps that is the thread Timeless occasionally finds.
If U dig: ‘Sometimes It Snows In April’, ‘Nothing Compares 2 U’ and ‘The Beautiful Ones’
So Who Is It For?
This is the paradox.
Another is the thought of a posthumous album in general. E
There is fantastic Prince music on Timeless.
There are fascinating discoveries. Historical rabbit holes. Moments when forty years collapse into seconds and you hear the same musical brain interrogating funk, rock, gospel, jazz, soul and pop from completely different points in his life.
For an obsessive, that’s heaven.
But Timeless still doesn’t convince me that this is how you introduce Prince to the next generation.
The Estate says one of its challenges is reaching younger listeners and argues, reasonably enough, that a ten-track record is more approachable than a sixty-track box set costing more than a hundred dollars.
But accessibility isn’t the same thing as brevity.
A young listener doesn’t need Prince made shorter.
They need Prince made inescapable.
Put Sign O’ The Times in films. Put ‘Erotic City’ somewhere nobody expects it. Get ‘Controversy’ into games, shows and culture. Make the live footage impossible to ignore. Let people encounter the astonishing finished work first.
Then, when they’ve lost their minds over Purple Rain, 1999, Parade, Sign O’ The Times and The Gold Experience, tell them there’s a song called ‘Heaven’ sitting in a Vault from May 1985.
They’ll come running.
That’s how Timeless makes sense.
Not as the front door.
As the secret staircase behind the bookshelf.
And perhaps that’s ultimately why I’m irritated by it while simultaneously knowing I’ll return to it endlessly.
I don’t need Timeless to prove Prince was a genius.
I already know.
I want the people controlling his extraordinary archive to understand what they possess.
Ten years after his death, Prince deserves more than content.
He deserves context.
Timeless contains five decades of it.
Sometimes beautifully.
But ten songs only leave me asking the same question Prince fans have been asking for years:
What else is in there?
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