40. The Very Best of Prince (2001)

There is no worse idea in this universe than trying to condense the entire career of Prince into a 17-song, money-grubbing compilation disc. Here was a man who made glorious, unadulterated albums, that deserve to be listened to from front to back until the end of time. There are B-sides, hidden treasures, and mind-boggling musical experiments across Prince’s four decade career, and he deserves better than this. No songs from Dirty Mind or Controversy? No “Soft and Wet?” The worst thing that came from Prince’s death was that this half-hearted compilation (with ugly “edited” versions of classic songs) became the best-selling album on iTunes, ahead of masterpieces like 1999 and Purple Rain. The iTunes description of the album literally states, “When Doves Cry’ serves as a reminder that Prince is also a stellar guitarist.” Gee, thanks for the reminder….

39. One Nite Alone (2001)

A bunch of schmaltzy piano ballads that equate to nothing, while also containing a song that seems to imply Abraham Lincoln was actually a racist who didn’t want the 13th Amendment passed, even though he actively fought for and pushed the 13th Amendment through a hostile Congress. Whatever. Originally released exclusively through his early 2000s NPG Music Club website, One Nite Alone is now only available through Jay-Z’s Tidal streaming service, which seems to specialize in exclusively streaming terrible music. If you’re looking for something better, I recommend an iTunes account, and literally any of the 38 albums listed below this one.

38. Chaos and Disorder (1996)

A purposely shitty album released by The Artist Formerly Known As Prince (or TAFKAP, as he came to be known) during his legal battles with Warner Brothers in the 1990s, Chaos and Disorder is an album of throwaway material that was never intended for public release (a fact that is blatantly admitted in the liner notes). This particular offering is a guitar-heavy collection of disjointed songs that Rolling Stone Magazine described as, “Like the work of a Prince impersonator — someone who has closely studied the star’s moves and mannerisms but has nothing new or substantial of his own to say.” Even still, when he was trying to be bad, he came away with one decent song; the anthem of personal empowerment, “I Rock, Therefore I Am.”

Key Tracks: “I Rock, Therefore I Am”

37. The Vault: Old Friends 4 Sale (1999)

The last of TAFKAP’s purposely terrible albums submitted to Warner Brothers to fulfill his contract, The Vault was presented to the record label at the same time as Chaos and Disorder in 1996, but was held for three years and released to little fanfare as the decade ended. Many fans complained that the supposed “vault” recordings were simply reworked compositions that had circulated in bootleg form for many years. The only highlight is the title track, “Old Friends 4 Sale,” which sounds like a long-lost James Bond theme song. A partnership that lasted over two decades, this would be Prince’s final Warner Brothers release until their renewed partnership for Art Official Age in 2014.

Key Tracks: “Old Friends 4 Sale”

36. The Truth (1998)

Prince’s skills as an acoustic guitarist were one of his greatest assets, highlighting his ability to play intimate settings, in stark contrast to the arena-dominating performances he was known for. So it’s a wonder that his only all-acoustic album, which was released in 1998 as a special fourth disc with the Crystal Ball package, is such a bore. Where live acoustic performances saw Prince as upbeat, and even quite funny in his banter with the audience, The Truth is a depressing showcase of low-energy songs that calls to mind a second-year graduate student pouring out his feelings in a coffee shop, instead of the most captivating performer of our generation. All the same, “Don’t Play Me” is an interesting take on the perils of fame from a man who tried to keep his private life very private.

Key Tracks: “Don’t Play Me,” “One of Your Tears”

35. The Slaughterhouse (2004)

Another NPG Music Club release of the 2000s, The Slaughterhouse might have proved more popular with fans had it been marketed for what it was — Musicology leftovers that didn’t make the cut. “2045: Radical Man” was included on the soundtrack for Spike Lee’s controversial film Bamboozled, though there was little promotion or even mention of the album outside Prince’s official website. “S&M Groove” plays with muffled guitar distortion, and “Props ’n’ Pounds” bounces along on a steady guitar lick. Strangely, the best moment of the album comes from the track “Peace,” which finishes with Prince speaking in an old man voice as he pokes fun at his name change while members of his band in the studio wail in uncontrollable laughter.

Key Tracks: “S&M Groove,” “Props ’n’ Pounds,” “Peace,” “2045: Radical Man”

34. The Rainbow Children (2001)

Look, I tried. Prince’s manifesto on his conversion to Jehovah’s Witnesses divides fans enough that some people think it a masterpiece, and others think it an overwrought jazz cluster that makes about as much sense as, well, the beliefs and doctrines of Jehovah’s Witnesses. Where Prince was spiritual in a metaphorical sense in the past, here he is downright Bible thumping. “Accurate knowledge of Christ and the Father will bring the everlasting now,” he sings, without ever revealing details of what that accurate knowledge actually is; and that’s from the most obvious song on the record (“The Everlasting Now”). For a guy who wanted everyone to get into Heaven, he could have made instructions more clear than, “Just like the sun, the rainbow children rise; flying upon the wings of the new translation.” Is someone else taking notes, cause I’m lost.

Key Tracks: “The Everlasting Now,” “Last December”

33. Plectrumelectrum (2014)

Since the early 80s, when he was flanked on each side by Wendy Melvoin and Lisa Coleman, Prince was always fond of multi-gender band dynamics. But where Wendy and Lisa gave Prince direction and musical spirit, his last all girl band, 3rdEyeGirl, produced nothing but muffled funk/rock confusion. No doubt the women of 3rdEyeGirl are talented musicians, but when their jam-band philosophy was put to an album, the entire effort comes off disorganized and soulless. Not surprisingly, their best songs come from moments in which they abandon their principles entirely and let Prince lead them in structured pop tunes.

Key Tracks: “StopThisTrain,” “AnotherLove”

32. The Chocolate Invasion (2004)

Released at the same time, and a virtual carbon copy of The Slaughterhouse in form and function, The Chocolate Invasion is ranked higher due to the inclusion of one of the great lost Prince tracks, “Supercute,” which is driven by a guitar over minimal production before climaxing into a chorus with as catchy of a hook as Prince released in the 21st century. How it was determined that the song wasn’t strong enough for Musicology or 3121 is beyond me. Another song, “The Dance,” was indeed reworked for release on 3121. Why Prince promoted this number and buried “Supercute” is just one of the countless mysteries of Prince song selection over the years. It remains one of his hottest tracks of the new millennium.

Key Tracks: “Supercute,” “The Dance”

31. HITnRUN Phase Two (2015)

Prince’s final studio album is a mix grab bag of old tricks that have worked better on previous efforts. From social consciousness (“Baltimore”), to hard rock (“Screwdriver”), Prince made better versions of these songs throughout his career, though one has to admire his ability to keep trying. “Xtraloveable” is a rework of a popular bootleg that was long overdue for release, while “RocknRoll Love Affair” is the highlight of the album — a straightforward pop/rock tune that works its way around an infectious saxophone hook before building to a singalong chorus that wins you over after a few listens, and proves that he still had the x-factor of songwriting craft until the day he died.

Key Tracks: “RocknRoll Love Affair,” “Xtraloveable,” “Groovy Potential”

30. HITnRUN Phase One (2015)

Released earlier in 2015 , and a slightly better original than HITnRUN Phase Two, Phase One stands out with the inclusion of “1000 X’s & O’s,” a deep R&B groove that recalls his early 90s work with the original lineup of the New Power Generation. “Hardrocklover” showcases his shredding abilities, while “Fallinlove2nite,” which was originally recorded with actress Zooey Deshanel, is a house dance song that plays with a synthesizer hook over pulsating beats. It’s Prince at his most fun, and it fit the scene perfectly when he premiered it during an episode of Deshanel’s Fox sitcom New Girl, in which Prince plays himself offering relationship advice. Did it make sense? No. Did I watch it? Yeah. It’s Prince…

Key Tracks: “Fallinlove2Nite,” “Hardrocklover,” “1000 X’s & O’s”

29. The Black Album (1988)

Recorded and ready for release in 1988, Prince’s last-minute shelving of his supposed “Funk Bible” generated perhaps slightly more mystery than it deserved (at one time it was considered the most bootlegged album in history). Prince’s reasoning for suddenly pulling the album range from a crisis of conscience to a bad ecstasy trip, but regardless, its sudden disappearance from the market made it a collector’s item until its official release in 1994. The bookends “Le Grind” and “Rockhard in a Funky Place” do indeed funk hard, but the curious moments are reserved for the hip-hop parody “Dead On It,” and the satirically violent “Bob George,” in which a deep-voiced Prince alter-ego imagines himself as a jealous husband whose wife is cheating on him with Prince, and the fight escalates into a shootout with police. Perhaps the weirdest song in the man’s entire catalog; and my friends, that’s saying something…

Key Tracks: “Le Grind,” “Cindy C,” “Bob George,” “Rockhard in a Funky Place”

28. 20Ten (2010)

20Ten had solid moments, if you could find it. In one of his final instances of inexplicable weirdness, Prince refused to release the album in the United States, instead including it with copies of the Daily Mirror in the United Kingdom (who, in exchange, wrote a suspiciously glowing review for the album). It’s a shame, because it actually has a few stellar tracks, including the vision of “Future Soul Song,” and the minimalist “Sticky Like Glue.” But the real winner is “Lavaux,” an upbeat journey across Europe in which Prince searches for the home he was never able to find. It’s a poignant moment disguised as a layered synthesizer hook.

Key Tracks: “Future Soul Song,” “Sticky Like Glue,” “Lavaux,” “Laydown”

27. LotusFlow3r (2009)

As the first decade of the new millennium came to a close, Prince was coming off a period of career-resurgence that was capped by the 3-disc set of LotusFlow3r, MPLSound, and Elixer (an album by protege Bria Valente), all released exclusively through Target retail stores. Though less polished than the rejuvenation trifecta of Musicology(2004), 3121 (2006), and Planet Earth(2007) before it, LotusFlow3r was still a solid rock effort, with the clever “Wall of Berlin” and uncomfortable history lesson of “Colonized Mind.” On “Dreamer,” Prince channels his inner-Hendrix as a like-minded guitar God should.

Key Tracks: “Colonized Mind,” “Feel Good, Feel Better, Feel Wonderful,” “Wall of Berlin,” “Dreamer”

26. Prince (1979)

The self-titled sophomore album from Prince was recorded before the Minneapolis prodigy could legally drink, but that didn’t stop him from being nasty from the start. “I Wanna Be Your Lover” is a straightforward R&B classic, while “Why You Wanna Treat me So Bad” showcases early guitar skills that would be brought front and center on later releases. Playing every instrument on the album at the age of 20, Prince also managed to write and record an early version of “I Feel For You,” which became a massive hit for singer Chaka Khan in the mid-1980s. Listening to the mellow earlier version demonstrates how Prince’s sound evolved rapidly and radically in a very short period of time. Prince is the sound of a young man on his way up.

Key Tracks: “I Wanna Be Your Lover,” “Why You Wanna Treat Me So Bad,” “I Feel For You”

25. Come (1994)

By the far the best and most structured of Prince’s contract-filler throwaways, Come is also his darkest album in tone and theme (the cover design is literally a tombstone marker, displaying the name “Prince,” with birth and death dates of 1958–1993). There are songs addressing issues of “Race,” while “Papa” seems to describe physical abuse Prince may have been subjected to during childhood. All of that is pushed aside though for the 90s R&B groove of “Letitgo,” one of his finest songs of the decade, and a personal career testament of troubled egos and mismanaged priorities. Putting his own behavior in check, it’s as honest and thoughtful a song as Prince ever wrote.

Key Tracks: “Come,” “Space,” “Race,” “Letitgo”

24. Lovesexy (1988)

Remembered more today for its controversial album cover and the circumstances surrounding its release, Lovesexy was by some accounts the final landmark of Prince’s “classic” period, starting in the early 80s and spanning nearly the entire decade. Filling in for The Black Album, which was shelved at the last minute, Lovesexy included the hit single “Alphabet Street,” as well as a leftover from The Black Album, “When 2 R In Love.” Contrasting the violence of The Black Album is “Anna Stesia,” a piano-driven allegory of religion and love that ends with the repeated refrain, ‘Love is God, God is love, girls and boys love God above.” Maddeningly, Prince envisioned the album as single sequence LP, and CD pressings were issued with every song bundled together in a single track, not allowing listeners to skip forward or backward. Despite several attempts at different points in my life, as a whole album, it’s the one piece from his classic period I’ve never been able to get into like the others. I can already imagine the message board comments…

Key Tracks: “Alphabet Street,” “Anna Stesia,” “When 2 R In Love”

23. Rave Un2 the Joy Fantastic (1999)

Rave Un2 The Joy Fantastic was TAFKAP’s attempt to re-emerge into the spotlight after a quiet period of his career, during which time he struggled with personal issues (including the death of his and Mayte Garcia’s son, and their later divorce). Originally structured as a “comeback” album of sorts, the collection of radio-friendly songs failed to make the impact Prince and Arista Records had hoped for, particularly after the sensational “So Far, So Pleased,” a duet with Gwen Stefani, was unable to be released as a single when Stefani’s own label blocked it. Still, there are positive moments sprinkled throughout the album. The title track is a reworked version of a song that had been in the vault since at least 1990, while “The Greatest Romance Ever Sold” is one of the more curious ballads in a career full of them. A cover of Sheryl Crow’s “Everyday is a Winding Road,” gets turned into an NPG funk jam, while the best moment is probably “Wherever You Go, Whatever You Do,” a final parting ballad to a former lover.

Key tracks: “Rave Un2 the Joy Fantastic,” “The Greatest Romance Ever Sold,” “Tangerine,” “So far, So Pleased,” “Everyday is a Winding Road,” “Wherever You Go, Whatever You Do,” “Prettyman”

22. For You (1978)

Prince’s debut album is a sort of nostalgic wonder. Here is an album entirely written, produced, and performed by a 19-year-old kid, who was allowed full creative control of his artistic vision by a major record company that bent to his will based on sheer talent alone. Even if the album sucked, that would still be impressive. Instead, it’s as polished of a record as a teenager can make. Though not well-received at the time, it has since become a necessity for any Prince collector, as the career that was to come is previewed across nine simple R&B tunes. The obvious highlight is Prince’s first single, “Soft and Wet,” a classic to this day, and probably the sexiest thing a teenager has ever conjured.

Key Tracks: “In Love,” “Soft and Wet,” “Just as Long as We’re Together”

21. MPLSound (2009)

Easily the best disc from the Target exclusive LotusFlow3r/MPLSound/Elixer package, MPLSound sees Prince returning to the minimalist synthesizers of his early 80s work, often to great effect. “(There’ll Never B) Another Like Me” is a sadly true declaration of fact, while “Dance 4 Me” builds on keyboard hooks and drum machines before reaching R&B euphoria. “Valentina” is an ode to actress Salma Hayek’s daughter, in which Prince sings, “Hey Valentina, tell your momma she should give me a call, when she gets tired of running after you down the hall.” I’ve got no other way to interpret that one: Prince really wanted to have sex with Salma Hayek.

Key Tracks: “(There’ll Never B) Another Like Me,” “Dance 4 Me,” “Valentina,” “Ol’ Skool Company”

20. Graffiti Bridge (1990)

Graffiti Bridge was the official soundtrack to the film of the same name, written and directed by Prince, and probably the worst movie ever made (seriously, it makes Under the Cherry Moon look like Citizen Kane). That said, as a standalone album, it was a strong effort that included, among others, “Thieves in the Temple,” a top 10 hit in the US. “New Power Generation” gave Prince’s backing band an official name, while “Round and Round” introduced the world to a young Tevin Campell. The Time, Mavis Staples, and George Clinton all make guest appearances, though the hidden gem on Graffiti Bridge is the Joni Mitchell-esque wordplay of “Joy in Repetition,” which turns into a searing guitar solo that lurks underneath Prince’s vocal pleas. It remains one of his great songs of the 1990s, and live renditions of it killed.

Key Tracks: “New Power Generation,” “The Question of U,” “Round and Round,” “We Can Funk,” “Joy in Repetition,” “Thieves in the Temple,” “The Latest Fashion”

19. Newpower Soul (1998)

Though technically an album credited to the “band” New Power Generation, Newpower Soul is a de facto Prince album, all the way down to the cover, which features only Prince and no one else. Consistently ranked as one of his worst albums, I find myself enjoying it more with each passing year for reasons passing understanding. In many ways, it’s greatest strength was its brevity, as fans were coming off the triple album of Emancipation (1996) and the 4-disc set of Crystal Ball (1998). As silly as it is lyrically, the title track got more than one party started in college, while “Come On” remains one of the great forgotten treasures of Prince’s career, in which he fawns over a woman, marries her, then begins to wonder if she’s a lesbian: “Could it be your girlfriend, who’s never ever been straight; when I ask you are you hungry, you say you already ate.” Meanwhile, “The One,” with a video directed by then wife Mayte Garcia, is a slow burner for the ages.

Key Tracks: “Newpower Soul,” “Mad Sex,” “Until U’re in My Arms Again,” “Come On,” “The One,” “Wasted Kisses”

18. Planet Earth (2007)

Following the greatest Super Bowl halftime show there will ever be (basically, a football game bookended a Prince concert), His Royal Badness had to come up with something a little more accessible than the religious meanderings he was prone to later in his career. So he straps on the guitar for “Planet Earth” and the aptly named “Guitar,” shows every R&B wannabe what a ballad is on “Future Baby Mama,” and reunites with some old friends for the good, clean, pop fun of “The One U Wanna C,” featuring Wendy and Lisa of The Revolution. “Chelsea Rodgers” is a pure funk workout from the last man who did it right, and just for good measure, he throws in a little mack-daddy hip-hop with “Mr. Goodnight,” which lays out Prince’s long-game seduction methods, involving a limousine, a transfer to a private jet, and something about a pool with a waterfall. He’s got me beat.

Key Tracks: “Planet Earth,” “Guitar,” “Somewhere Here on Earth,” “The One U Wanna C,” “Future Baby Mama,” “Mr. Goodnight,” “Chelsea Rodgers”

17. Emancipation (1996)

Finally free of his contractual obligation to Warner Brothers, TAFKAP celebrated with the most ambitious R&B album of its time — A triple disc set of all new music, featuring uptempo jams (“Jam of the Year”), some hip-hop sprinkled in (“Right Back Here In My Arms”), shots at his former record label (“Face Down”), a few killer covers (“One of Us,” “La, La, La Means I Love You”), and an album’s worth of material in dedication to his new wife, Mayte Garcia (the whole second disc). Some of it works, some of it doesn’t, but it’s never not interesting; and when the greatest musician of his generation is given 36 tracks to work with, he’s bound to land some punches. The one that hits hardest is “Somebody’s Somebody,” in which the song’s lonely narrator begs to have someone care about him. Anyone who’s ever been the awkward fifth wheel can relate.

Key Tracks: “Jam of the Year,” “Right Back Here in My Arms,” “Somebody’s Somebody,” “White Mansion,” “Sex in the Summer,” “Face Down,” “La, La, La Means I Love You,” “Style,” “Sleep Around,” “My Computer,” “One of Us,” “Emancipation”

16. 3121 (2006)

Anyone thinking Prince ever lost his touch should listen to the first four songs of 3121, which are as rich and varied as any four songs he put in sequence together his whole career (and this was two decades after his most popular output). From experimental rock (“3121”), to bouncy pop (“Lolita”), to acoustic island balladry (“Te Amo Corazon”), to synth-driven R&B (“Black Sweat”), 3121 is a Hall of Fame inductee still in control, with no sign of stopping. Even the church stuff works on “The Word,” which is a genuinely cool song about the Bible, as well as the horn blasts of “Get on the Boat,” which has a pretty obvious Judeo-Christian allusion. And if you never saw what he made that guitar do on Saturday Night Live with “Fury,” you need to remedy that right now.

Key Tracks: “3121,” “Lolita,” “Te Amo Corazon,” “Black Sweat,” “Fury,” “The Word,” “The Dance”

15. The Gold Experience (1995)

So he changed his name to an unpronounceable symbol, feuded endlessly with his record label, and did as much as he could to alienate every last casual fan still hanging on from the 80s. But for those diehards, could he still make a great album? Hell. Yes. This guy showed up in public with the word “slave” scrawled on his face and still managed to win the casuals back with the dreamy “The Most Beautiful Girl in the World.” If there was ever any worry that Prince’s genius had evaded him in the same manner that Stevie Wonder lost the magic after his 1970s output, The Gold Experience effectively ended it. “Pussy Control” is forward-thinking feminist hip-hop that has yet to be equaled by actual rappers, while “Shhh” remains his most underrated “get to the bedroom” plea. There’s still the Prince of old, trying to guide us to some heavenly realm with the guitar solo at the end of “Gold,” which doesn’t quite muster that “Purple Rain” aura, but it tries. And if you want to hear Prince the storyteller, look no further than the exquisite “Shy,” which dances on a twangy guitar lick and begins like a guilty-pleasure book: “After a month of just being alone, he said, ‘I wonder what LA’s thinkin?” Anyone who thought the Purple Maestro was down for the count would have been pleased to learn this son of a bitch wasn’t even 50% through his career yet.

Key Tracks: “Pussy Control,” “Shhh,” “We March,” “The Most Beautiful Girl in the World,” “Now,” “Shy,” “Billy Jack Bitch,” “Eye Hate U,” “Gold”

14. Crystal Ball (1998)

Try to ignore the fact that the release of Crystal Ball was the most innovative and the most disorganized release by a major recording artist of all time. Try to ignore that Prince preceded the iTunes revolution by selling his album online in an era before household internet was commonplace, and also try to ignore that it nearly killed any semblance of a devoted fanbase he had left. Of all the things written about TAFKAP’s most notorious 90s release, try to remember that underneath it all was a pretty stellar collection of songs. Yes, the release of Prince’s official bootleg collection, featuring Prince-approved vault recordings, was a disaster (many fans received their 3-disc set months after promised delivery dates), but the music more than made up for it. The avant-garde “Crystal Ball” and wicked “Dream Factory” are leftovers from the aborted Crystal Ball project of 1987, which was cut down to a double album and turned into Sign O’ the Times, while “Movie Star” (originally written for The Time) is as tremendously silly as Prince could get. “Da Bang,” which was written and recorded in one day, is stop-start speed rock at its finest, and a live rendition of the “The Ride” remains his greatest blues-rock accomplishment. With so much varied material, I often wonder why I come back to “Acknowledge Me” more than any other song. Over a looped horn sample, Prince creates the 90s R&B jam to end them all. All he wants is a little acknowledgement: “I was here in the beginning, and I’ll be here forevermore.” Truer words were never spoken.

Key Tracks: “Crystal Ball,” “Dream Factory,” “Acknowledge Me,” “Love Sign, “2morrow,” “Movie Star,” “Interactive,” “Da Bang,” “Calhoun Square,” “Crucial,” “Sexual Suicide,” “Good Love,” “Days of Wild,” “Last Heart,” “18 & Over,” “The Ride (Live)”

13. Controversy (1981)

It’s difficult to court controversy when you still haven’t landed a top 10 hit four albums into your career, but already Prince was turning heads. “I just can’t believe all the things people say,” he sings on the opening title track, “Am I black or white, am I straight or gay?” He never answers the question, and so we’re left with the mystique of the man we called Prince — The one who says, “Sexuality” is all he’ll ever need, amidst cries of “Do Me, Baby.” But there’s something slightly more sensual than you might expect from the sex-crazed sultriness of this early Prince masterpiece. On “Private Joy,” he walks a very thin line between devoted and creepy, declaring, “I strangled Valentino, you been mine ever since; if anybody asks, you belong to Prince.” Somehow, in the middle of all the baby-making, he gets more overtly political than he did his entire career: “Ronnie talk to Russia before it’s too late, before they blow up the world.” Solid advice, but I’m not sure what a full rendition of the Lord’s Prayer is doing in the middle of “Controversy” except to be, you know, controversial. But at the end of the day, he wasn’t above grand gestures. “I can’t give you everything you want, but I can take you to a restaurant,” he sings over rockabilly synths, “If you’re not hungry, I’ll jack you off.” That’s….sweet of you? Let’s be real; Controversy is as filthy of an album as the day it came out, and with scratchy synthesizers and guitar work that moved from needlepoint funk to shredded distortion, it’s still the most fascinating indicator of what was about to happen over the next three years. Controversy is what genius sounds like as it’s coming to a boil.

Key Tracks: “Controversy,” “Sexuality,” “Do Me, Baby,” “Private Joy,” “Let’s Work,” “Jack U Off”

12. Diamonds and Pearls (1991)

The first of two albums officially credited to “Prince & The New Power Generation,” Diamonds and Pearls is an unabashed return to R&B, and perhaps his “blackest” album in over a decade, as he sought to regain the prominent African-African audience he had lost with the European influences of Around the World in a Day and Parade. The pure sexuality of “Cream” returned Prince to the top of the Billboard charts with his fifth #1 single, and he later turns up the nastiness with the funk/rock of “Gett Off.” Then there’s “Daddy Pop,” an early foray into hip-hop culture, where Prince talks smack with an astonishing vocal range that moves from deep baritone to falsetto on the same measure: “See all my critics wastin’ time; worrying ‘bout the daddy while he beat you blind.” (The live performance on the Arsenio Hall Show is perhaps the most underrated television appearance of his career, in which Prince jumps, splits, dances on a piano, and funks out with an energy that would tire James Brown). And after all the free love, uptempo numbers have left you in a sweat, there’s “Diamonds and Pearls,” the song that rewards age and maturity more than anything in his catalog. “There will come a time, when love will blow your mind, and everything you look for, you’ll find.” I’ve listened to it my whole life, and only now, as a married man, am I starting to get it. Even the social-consciousness of “Money Don’t Matter 2 Night” still seems relevant more than two decades on, as Prince ties in gambling addictions with America’s penchant for foreign wars where oil is concerned. If nothing else, Diamonds and Pearls was an album of bona fide hits that politely reminded the world that Prince could make himself relevant like regular people flip on a light switch.

Key Tracks: “Thunder,” “Daddy Pop,” “Diamonds and Pearls,” “Cream,” “Get Off,” “Walk Don’t Walk,” “Money Don’t Matter 2 Night,” “Push”

11. Art Official Age (2014)

Call it revisionist history (or over sentimentality), no album looks better in retrospect than Art Official Age. It has grown in stature so fast in such a short amount of time, one has to do a double-take of the release year just to make sure they aren’t mistaking this space-age odyssey for some long-lost 80s masterpiece stolen from the Paisley Park vault. No, this is the Prince of this decade; 54-year-old Prince, still setting the bar for everyone from Janelle Monae to Daft Punk. “The gold standard, crazy amazing, upper echelon of groove,” he chants on “The Gold Standard,” before proceeding into a electric funk workout that sounds as if it time traveled from Side A of Sign O’ the Times, like some sort of 21st century “Housequake.” “Art Official Cage” morphs from disco guitar licks into opera-suite storytelling into the sound of a man being waterboarded. “We need you to tell us what you know,” says the torturer, voiced by Prince, as he ostensibly works to bring some truth out of himself. The man who resisted computer culture with “Something in the Water (Does Not Compute)” three decades before seems to have woken from a deep sleep (“Mr. Nelson, can you hear my voice”), but offers the same hesitation in the era of texting romance. “We’re getting high on something that doesn’t require clouds,” he sings on the superb “Clouds,” as he offers more intimate advice: “You should never underestimate the power of a kiss on her neck, when she doesn’t expect.” It’s quite possibly the best song he released this century, but even Prince understood all grooves come to an end. On the ethereal “Way Back Home,” the most guarded musician of our time opens his soul for the world to interpret: “Most people in this world are born dead, but I was born alive; with a dream outside my head, that I could find my way back home.” His home planet? That purple Heaven in the sky? Wherever home is, with a final parting masterstroke of this quality, I like to think he found it.

Key Tracks: “Art Official Cage,” “Clouds,” “The Gold Standard,” “U Know,” “Breakfast Can Wait,” “This Could Be Us,” “Way Back Home,” “FunknRoll”

10. Musicology (2004)

The full scope of Musicology on Prince’s career and legacy is still dramatically under-appreciated. In the wake of his death, with never-ending coverage and countless tributes by fellow musicians, it’s easy to forget that as the year 2004 began, Prince’s career was effectively over. It had been nearly a decade since Emancipation, his last decently promoted album, while his final commercial effort of the 1990s, Rave Un2 the Joy Fantastic, fell flat with fans and audiences. His last two efforts had been his ode to Jehovah’s Witnesses (The Rainbow Children) and the all-instrumental N.E.W.S. Furthermore, other artists were beginning to move into Prince territory with their own work (namely, D’Angelo’s Voodoo and Andre 3000’s The Love Below), positioning themselves as natural successors to a genius who had long ago lost himself in his own ego. Without Musicology, our lasting image of Prince may have been Kevin Smith’s hilarious story about trying to shoot a documentary at Paisley Park (“Prince has been living in Prince-world for some time now.”)

Then, like a scream out of the night, there he was. There was the Grammy performance with Beyonce, then the Rock and Roll Hall of Fame induction, then Musicology, his most polished, straightforward work since who could remember when. “Musicology” opens with that trademark wail before bouncing over a funky bassline. “Illusion, Coma, Pimp & Circumstance” displays a sense of humor rarely found on funk of this magnitude, as an older woman takes in a young stud, exchanging her acquired wealth for his good time, while “A Million Days” sees Prince pleading with his woman to return over guitars and vocal harmonies. The double knockout of “The Marrying Kind” and “If Eye Was the Man In Ur Life” is a pop/rock composition of the highest order, though “Life O’ the Party” offers a breakdown unlike anything in his catalog, calling out critics and addressing his legacy in the most entertaining manner possible (“He don’t play the hits no more, plus I thought he was gay?”). Then there’s “Cinnamon Girl,” which tells the story of a young American Muslim facing discrimination after 9/11: “9–1–1 turned that all around, when she got accused of this crime; so began the mass illusion, war on terror alibi.” An easy thing to say in 2016, but not so easy in the early days of the Iraq War. Though it’s not all so serious — The album ends with “Reflection,” one of the more beautiful and tender acoustic ballads of his career (the live version with Wendy Melvoin says it all).

I’m sure some purists think I’m ranking Musicology too high, but it shouldn’t be forgotten how this album pulled Prince from the nostalgic depths of my parents’ generation and re-introduced him to an entirely new fanbase who had grown up on his hits, but had failed to understand the man in the living flesh. In one fell swoop, he went from weird personality of the past to elder statesmen of rock and roll, setting up a series of albums and television appearances that cemented him as the most talented performer of the era. Without Musicology there is no Super Bowl halftime show, no “Black Sweat,” no surprise American Idol appearances. In one crucial moment of his career, Prince made the decision to not die, but rather, dance his life away.

Key Tracks: “Musicology,” “Illusion, Coma, Pimp & Circumstance,” “A Million Days,” “Life O’ the Party,” “Call My Name,” “Cinnamon Girls,” “What Do U Want Me 2 Do?” “The Marrying Kind,” “If Eye Was the Man in Ur Life,” “Reflection”

9. Dirty Mind (1980)

Certainly the Beatles, the Rolling Stones, and Stevie Wonder evolved their sound from record to record; but no artist, before or since, has ever made the type of 180-degree turn 22-year-old Prince Rogers Nelson made with his first masterpiece, Dirty Mind. On his first two albums, Prince was a Stevie Wonder prototype — a significant talent for sure — but one playing relatively standard R&B for the 1970s. With a new decade in front of him, Prince flipped the script of an entire career, changing his sound, image, and clothing choices into that of a Minneapolis sex freak who was going to push the boundary of what black musicians were allowed to do. Rather than use traditional horns for emphasis, Prince structured melodies around synthesizers, recording the entire album in his home studio and cutting the tracks down to their bare-bone parts. Indeed, Dirty Mind still sounds like a collection of brilliant demos recorded in a basement. It solidified his songwriting template (later known as the “Minneapolis Sound”) and changed the lives of those who heard it, as Prince began to establish himself as the adult-alternative to Michael Jackson. Halfway across the country, Anthony Kiedis heard the title track and decided to start a group called the Red Hot Chili Peppers.

“Dirty Mind” sets the tone early: “There’s something about you baby, it happens every time; whenever I’m around you baby, I get a dirty mind.” And folks, that’s about as tame as it gets. “When You Were Mine” is an emo-lovers dream (influencing every song Fall Out Boy ever recorded), as Prince talks about a threesome gone awry when his girlfriend seems to take more to the second man. “Do It All Night” is piano-driven funk that dares you not to dance to it, while “Uptown” celebrates the androgynous Minneapolis music scene that would be immortalized four years later in the film Purple Rain: “She said ‘Are you gay?’ Kinda took me by surprise, didn’t know what to do; just looked her in her eyes, and I said, ‘No, are you?” Then there’s “Head,” which literally caused early-Revolution keyboardist Gayle Chapman to quit the band when she refused to perform lyrics about a woman who gets picked up by Prince on her way to her own wedding and loses her virginity to him instead. Chapman was replaced by Lisa Coleman, beginning an important six year partnership that helped Prince expand his musical palate. And then there’s “Sister.” Yeah, I’m not even touching that one…

Key Tracks: “Dirty Mind,” “When You Were Mine,” “Do It All Night,” “Uptown,” “Head,” “Partyup”

8. Parade (1986)

Parade represents Prince at the height of his talents as a musical collaborator. Though known as a solo genius who played every instrument on many of his songs (including songs here), much of Prince’s musical direction at the peak of his fame was guided by the greatest band he ever assembled — The Revolution. It’s no wonder that many members of The Revolution name Parade as their favorite album from their time with Prince. A sprawling piece of psychedelia, segueing from European suites to orchestral instrumentals to minimalist pop, Parade remains the grandest experiment ever concocted by His Royal Badness, and unlike anything a major recording artist has released at the height of their fame.

As the soundtrack to the film Under the Cherry Moon (a conversation for another time, but let’s just say, the music is better than the movie), Prince expanded on the European sound previously explored on Around the World in a Day, incorporating a full orchestra for the first time in his career. The first four tracks operate as a single suite, and the drum pattern for all four was laid down in a single continuous take by Prince, who kept the tempo and measures in his head, knowing when to slow down and accelerate based on the time signature change (I can’t make this up). Of course, “Kiss” was the hit, Prince’s third #1 single. The spare, bass-less track began as a 60-second demo Prince recorded with an acoustic guitar, giving the tape to funk band Mazarati and producer David Z, who reworked it substantially before sending it back to Prince, who appreciated the work so much he kept Mazarati’s background vocals in his final mix. Though “Kiss” gave the album it’s most noteworthy song, Parade has deep cuts that deserve to be heard. “Sometimes It Snows in April” is perhaps the most heartbreaking song of his career, and D’Angelo’s performance of the song on The Tonight Show is the finest tribute to Prince I’ve seen thus far. But the best moment is reserved for “Mountains,” one of the most criminally underrated singles of the 1980s. Written by Revolution members Wendy and Lisa, “Mountains,” builds on a drum machine pattern over layered synths, creating a surprising jam that seems to carry on indefinitely, though never outstaying it’s welcome. It’s one of the best Prince songs you’ve never heard.

Key Tracks: “New Position,” “Girls & Boys,” “Venus de Milo,” “Mountains,” “Kiss,” “Anotherloverholenyohead,” “Sometimes It Snows in April”

7. Around the World in a Day (1985)

“Open your heart, open your mind,” Prince instructs his listeners on the opening title track of Around the World in a Day — valid instructions coming from a man looking to abandon the very foundation of what made him a star. Less than a year after the release of the multi-platinum mega-success of Purple Rain, Prince sent copies of Around the World in a Day to radio stations with no instructions for singles, and no indication of what to think. The biggest rock star on the planet had just thrown his next curve ball, vacating the pop/rock of Purple Rain and replacing it with Beatles-esque 60s pop, complete with Middle-Eastern influences and psychedelic experiments. Certainly, Prince could have rested on his laurels and released some version of Purple Rain 2, but the man who had changed the course of popular music at least twice by the age of 27 could not be put in a box. Around the World in a Day is a stunning declaration — Prince was willing to sacrifice both casual fans and critical consensus to realize his vision. There were no corporate strings dictating the next move. At no point was there any doubt that this was the music Prince wanted to make.

“Around the World in the Day” immediately transports the listener far from the safe confines of Minneapolis with its Middle-Eastern flute, almost designed as a polar opposite sound to the church organ that “Let’s Go Crazy” opened with a year before. “Paisley Park” would give his future recording studio a name, utilizing Beatles melodies against Prince vocal layers. “America” is a funk workout that lifts a chord progression from “America the Beautiful” before using the recognizable melody to satirize 1980s American culture and the fear of nuclear war (“Nothing made Jimmy proud, now Jimmy lives on a mushroom cloud”). Then we have “Pop Life,” another seriously underrated Prince single, in which he contemplates his new-found fame and comes to terms with the realization that some people will never appreciate him. Notably, the songs cuts to an actual audio recording of a 1981 concert in which Prince, opening for the Rolling Stones, is booed off the stage by Stones fans who didn’t understand what they were seeing (I’ll avoid commenting on the unbearable irony of Rolling Stones fans, a band completely indebted to black popular music and huge Prince fans themselves, booing the man who would eventually be one of the greatest black musicians of all time). Between political statements, and grand genre swings, it’s all a very avant-garde affair, until you get to “Raspberry Beret.” Perhaps the single most accessible song in Prince’s entire catalog, it tells a rather normal story of teenage romance and losing virginity that, though we’ll never know if it truly came from Prince’s life, he makes the listener feel like it did. It is an infectious, addictive, pop song for the ages, and one of the great hallmarks of an illustrious career.

Key Tracks: “Around the World in a Day,” “Paisley Park,” “Raspberry Beret,” “America,” “Pop Life,” “The Ladder”

6. Batman (1989)

Whoa, whoa, whoa…Batman ranked ahead of classic recordings like Parade and Controversy? Batman ranked ahead of career-defining hits like Diamonds and Pearls and Musicology? The Batman soundtrack….ranked ahead of Dirty Mind??? Yes, yes, and yes. Say what you will, Prince’s mind-boggling soundtrack for Tim Burton’s 1989 vision of Batman, starring Michael Keaton as the Caped Crusader, is one of the greatest mass-marketing experiments of all time, and is Prince’s reigning misunderstood masterpiece. The Batman soundtrack is a popular culture event that will never, I mean never, exist again in any form. It would be the equivalent of Taylor Swift writing the soundtrack for Captain America. Never again will a popular recording artist be given free creative control in interpreting a classic comic book hero in musical form for a major motion picture (and no, U2's disastrous Spider-Man Broadway musical does not even come close to the scope of what this was). This was the shot — history’s one moment to achieve a type of studio crossover success that has not been replicated since, and Prince absolutely nails it to the fucking wall.

Working as a sort of “Batman opera,” Prince utilizes audio clips from the film to write songs from the perspective of different characters. The album opens with the ambient noise of Gotham and a soft piano interlude before we hear Keaton’s Batman telling a criminal, “I’m not going to kill you. I want you to tell all your friends about me.” The drum and bass kick in for “The Future,” then we hear Bruce Wayne’s declaration: “I’m Batman.” “Electric Chair” is a psychological breakdown of fractured Gotham citizens (“If a man is considered guilty for what goes on in his mind, give me electric chair for all my future crimes”), while “The Arms of Orion” is essentially a Broadway show-tune about Batman and Vicki Vale, which would annoy a listener if they weren’t so surprised by the fact that Prince actually has this club in his bag, and it works. “Partyman” is all Joker, and the song itself is used in the film for the scene in which Jack Nicholson and his cronies vandalize an art museum, though the music video went deeper, with Prince in a half-Batman, half-Joker costume, of which filmmaker and culture critic Kevin Smith summarized, “He’s the motherfucker that was talking about the dichotomy of Batman, and Bruce Wayne, and the Joker, long before anyone else.”

Then there’s the sensational “Vicki Waiting,” from the perspective of Bruce Wayne, who can’t commit to a relationship due to his alter-ego. It makes the billionaire sound somewhat normal (“The talk of children still frightens me”) as he accepts that the chaos of his beloved city may never go away (“All is well in Gotham City, the sound of terror is all you hear”). The album concludes with the reprise of “Batdance,” which recalls elements from all the tracks before spiraling into an industrial funk climax. Somehow, it became Prince’s fourth #1 single; far and away the strangest song in contemporary music to ever top the charts.

Finally, if there is any reason to appreciate Batman, it’s this: It is, without question, Prince’s most underrated guitar album. Previous efforts like Around the World in a Day and Parade had seen him abandon the instrument almost entirely. Here, there is an unparalleled mix of funk guitar licks and serious axe-shredding. Check out the rhythm guitar of “Electric Chair,” or the undercurrent of emotion with the six-string on “Vicki Waiting.” Meanwhile, “Batdance” flips back and forth between rock showmanship and eclectic funk in a way no other musician could ever equal. In one song, he creates a testament to his ability to play multiple genres and styles without missing a beat. It’s the most daring, fearless work of Prince’s career. Or, maybe I’m just a little bit crazy. Ever dance with the Devil in the pale moonlight?

Key Tracks: “The Future,” “Electric Chair,” “The Arms of Orion,” “Partyman,” “Vicki Waiting,” “Lemon Crush,” “Scandalous,” “Batdance”