Ranking the Grammy Winners for Best Pop Vocal Album

When the worst album that Steely Dan ever released ends up not only winning Best Pop Vocal Album but also Album of the Year, you know that the votes aren't necessarily about the music so much as they are about the narrative. After all, the Dan has a litany of legendary albums under its belt, but out of the six nominations received in the '70s and '80s, the band had always entered Grammy afterparties without a single trophy in hand. Thus, the Grammy Award's 43rd iteration served as a severe case of course-correction, acknowledging the Dan just for being the Dan without listening to any of the music itself, as the lifeless, horned-up, bland and forgettable "Two Against Nature" only illustrated why some artists maybe shouldn't reunite after a decade's absence.

Anyone who follows the Black Eyed Peas knows that they started so earnestly, as their first two albums were genuine, fun-filled throwback rap records with a deep-seated knowledge of hip-hop's storied past. Then with 2003's "Elephunk", the introduction of Fergie also meant the group started leaning into a pop-heavy sound; a textbook case of selling out. Leader will.i.am dumbed down his lyrics to an astounding degree, but the platinum plaques kept stacking up, no more so than on "The E.N.D.", their biggest album to date. To be honest, once you get past boneheaded smashes like "I Gotta Feeling" and album-track dreck like "Missing You," there's some fun takeaway moments on here ("Meet Me Halfway," that beat switch on "Imma Be"), but the Black Eyed Peas' so-dumb-it's-fun run of hits has definitely hit its expiration date, which is why a decade later, their sound truly feels three-thousand-and-late.

No one here is disputing Ed Sheeran's popularity or his ability to write an endless stream of songs that are exclusively designed to be played as the first dance at a wedding. What is surprising, however, is how this earnest busker with a sweet charisma has turned into a full-on pop star, and as such, has started believing his own hype to an unfortunate degree. "÷" (or "Divide" as it is sometimes referred to) is without a question Sheeran's biggest album ever, and while not as blatantly commercial nor as shallow as his dreadful 2019 effort, "No. 6 Collaborations Project," "÷" feels less like a record of new songs so much as a playlist — one where every track ties in some element meant to appeal to listeners outside his fan base. From the Irish fiddlework in the slightly problematic "Galway Girl" to the U2-isms of "Castle on the Hill" to the oh-god-he's-rapping-again pose of "New Man" (to say nothing of the Deluxe Edition tracks like "Bibia Be Ye Ye"), "÷" feels less like the work of an artist and more like that of a businessman who will corner you in a pub and drunkenly tell you all the exciting and cynical ways in which he's now "expanding his brand." To his credit, his roadmap-to-superstar-status gambit worked here, but his real fans are keenly aware that the more popular Ed gets, the worse his albums become.

Long lost in the commercial wilderness for the longest time, Ray Charles was staging a comeback in 2004 but sadly never got to see any of it come to fruition, as he passed away in June of that year at age 73. In August, his long-in-the-works "Genius Loves Company" appeared, where Ray duetted with a who's-who of adult contemporary favorites, from Bonnie Raitt to James Taylor to Diana Krall to Michael McDonald. In October, the Jamie Foxx-starring biopic "Ray" was released and soon netted Foxx an Oscar for his performance, right after "Genius Loves Company" won the Grammy for Album of the Year. It was a sweet vote to acknowledge a true legend, but at the end of the day, "Genius Loves Company" amounts to little more than pleasant background music, as the on-the-nose Phil Ramone production brings in cinematic string sections that blanket the album in a professional sheen that ends up vacuum sealing every vocal performance into nothing more than cold, hard product. "Genius Loves Company" is both polished and pandering at the same time, with the end result being a career grace note that's both inoffensive and utterly inessential.

Bonnie Raitt struggled to find an audience for her modern blues-rock sound for most of her early career, not securing true commercial success until her 10th full-length, which partnered her with the great Don Was, the man who backed Raitt's guitar solos and songwriting with just the right amount of color to make it pop on the radio. That resulting album, "Nick of Time," was a monster smash that netted Raitt the Grammy for Album of the Year, with her two follow-up albums reuniting her with Was to basically deliver more of the same. Truly a trilogy of "if it ain't broke, don't fix it" records, "Longing in Their Hearts" netted Raitt her first-ever Canadian chart-topper with the hit "Love Sneakin' Up On You," and most of "Longing" careens between safe blues-rock fair and earnest balladeering on tracks like "Dimming of the Day" and "Storm Warning." Very much a product of its era, "Longing" hasn't aged particularly well with its stilted production and keyboard textures, but it remains an enjoyable (if somewhat forgettable) listen regardless.

The James Taylor of the '70s was a soft-rock behemoth, consistently putting out pleasant puffs of folk-inflected soul-pop like a machine, topping charts and moving units by the truckload. The James Taylor of the '80s and '90s, however, was more reserved, and the span between 1991's "New Moon Shine" and 1997's "Hourglass" was his longest break between albums at the time. Stripped-down (well, as stripped-down as you could get for a James Taylor album) and sometimes bordering on confessional, "Hourglass," more than anything, was an agreeable record that honestly felt like a return to form simply because his fans hadn't heard from him in so long. There were guests aplenty (Stevie Wonder, Branford Marsalis, Yo-Yo Ma, Sting), and "Little More Time with You" was a soft hit, but tracks like the warm "Gaia" and the slow-dance favorite "Up From Your Life" balance out dated fluff like "Jump Up Behind Me," all of this adding up to a perfectly palatable new James Taylor record.

No matter what you think of former *NSYNC frontman Justin Timberlake's musical output, the man, especially at his peak, had undeniable charisma, working extremely hard to make us like him. His first solo album, "Justified," is a bit bloated (no track is under four minutes), and some of The Neptunes productions sound a bit stale some two decades later, but the moments that work still sound fresh. "Señorita" rides a startling-minimal Latin groove to seductive success, and "Cry Me a River," unsurprisingly, remains a generational pop music touchstone. Heck, it was an album that was so charming, there was even a track made out of Timberlake's beatboxing and a Bubba Sparxxx verse ("Right for Me") and we, as a species, still gave JT a pass. Guess he was "Justified" in going solo after all.

Following 1992's acclaimed "Love Deluxe," the members of Sade all went to pursue other projects, forming bands like Sweetback and getting heavily involved with neo-soul pioneer Maxwell. That 1992 hit single, "No Ordinary Love," remained a radio staple for years down the line, which is why as the new millennium approached, the band decided to get back together, resulting in the long-overdue "Lovers Rock." Aiming straight for that Quiet Storm sweet-spot, Sade has perfected the art of making a good Sade album, and "Lovers Rock" is no exception, as "Flow" features some drum work straight out of a trip-hop number and "By Your Side" serving as this record's big play for radio. Of note, however, are the times when Sade injected a bit more political passion in the subject matter, as addressed on "Slave Song" and especially the powerful "Immigrant," proving that after all this time, there are still small new innovations that Sade is finding in its sound.

In Bruno Mars' surprisingly sparse discography, undeniable pop gems ("Just the Way You Are", "Finesse") rub shoulders with records that, to put it simply, can sometimes be amateur's night in the lyric department ("The Lazy Song", "24K Magic"). These awkward ends mean that no album of his is truly consistent, and "Unorthodox Jukebox," his sophomore effort, remains that awkward middle child. The highlights are undeniable: the throwback dance-soul of "Treasure," the deliberate Police tribute "Locked Out of Heaven," the earnest piano ballad "When I Was Your Man," etc. The awkward moments this time out aren't outright horrible (although "Gorilla" is a hell of a curiosity), but the stylistic detours swerve between the obvious (the reggae-kissed "Show Me") and the extraordinary (who knew the alt-rock of "Moonshine" would fit Bruno so well?), ensuring that of all his albums, "Unorthodox Jukebox" is his most aptly titled.

For a whole generation of youths, Celine Dion is always going to be known as that singer with that song from "Titanic" and may gloss over the fact that before her heart went on, she was already one of the biggest pop stars on the planet, and "Falling Into You" was her American coronation as the Queen of Adult Contemporary. Essentially one of the biggest soft-rock albums in history, "Falling Into You" was anchored by smashes like "Because You Loved Me" and her other signature hit, "It's All Coming Back to Me Now." Lyrically, the album can traverse across some surprisingly dark themes, even if some of the production choices — particularly the tinny horn sections — have aged terribly. Yet what's never in dispute is Celine's vocal prowess, and across all of this record, she is at the peak of her powers, perhaps no better exemplified by her extraordinary, rafter-shaking rendition of "All by Myself," which proves why Cline put the "Vocal" in Best Pop Vocal Album 

In the Great British Diva Sweepstakes of the late 2000s, Duffy got off to a strong start with her debut album, "Rockferry," before falling under the shadows of both Amy Winehouse and Adele. It's a real shame, too, as "Rockferry" is a lovely, now-forgotten album that was so much more than her plucky hit single, "Mercy." Working with some slightly unusual collaborators (like Suede's Bernard Butler), Duffy crafted a record that belonged to no particular style or decade, instead hand-picking sounds from her favorite eras and playing around with them to suit her needs. Whether it be sassy girl group numbers (like on the mid-tempo strut of "Delayed Devotion"), Motown soul ("Warwick Avenue," which is constantly on the verge of breaking out into "Sittin' On the Dock of the Bay"), or even contemporary takes on disco ballad aesthetics ("Serious"), Duffy's debut remains an undeniable delight, even if it was a flash in the pan, as her sophomore effort flopped and she has put out few songs since then. 

With 11 Grammy nominations under her belt, it's surprising that "Sweetener" earned the pint-size pop diva's first win. But as big as "Sweetener" was upon release, it was a shadow of the planet-swallowing monster she would drop on us months later in the form of "thank u, next," her finest full-length. As many critics noted at the time, "thank u, next" was the album that Ariana fans wanted from her instead of "Sweetener," which, to be honest, was still a lot of fun despite some obvious flaws. "Sweetener" suffers under the weight of some truly atrocious Pharrell productions (including "the light is coming" — arguably the worst song she's ever released), but epic pop numbers like "God is a woman," "everytime," and "breathin" helped solidify Ariana as arguably the defining pop diva of the decade. While each of Ariana's albums is stacked deep with a new year's worth of Top 40 fodder, "Dangerous Woman" and "Sweetener" really showed Ari truly discovering her own artistic voice — something that she perfected with "thank u, next." While "Sweetener" is not without some bloat, it's still a thrill to hear big-budget dance-pop done right, and "Sweetener" remains stuffed with some truly sweet moments. 

The thing about a Kelly Clarkson album is that when she aims for that big pop spectacle, it damn near feels like no one can do it better. Tied with Justin Timberlake as the single most nominated artist in this category (and sharing the same space with Adele with two wins apiece), Kelly knows how to deliver a showstopper and manages to do so here with ballads like "Standing in Front of You" and "Breaking Your Own Heart." This isn't Kelly's strongest album (tracks like "Mr. Know It All" and the profoundly stupid "Einstein" hinge on terrible lyrical conceits), but when she leans into her classic rock-pop sound on "I Forgive You" or teams up with uber-producer Greg Kurstin on tracks like "What Doesn't Kill You" and "Dark Side," it feels like Kelly is the definitive diva of the moment, and all of pop music is "Stronger" because of it.

If Sam Smith's debut album is anything, it's incredibly earnest (and perhaps maybe even a little pretentious, given the Deluxe Edition rerelease was subtitled "The Drowning Shadows Edition"). Crafting many (many) tales of heartbreak across its 10 tracks, "In the Lonely Hour" walks a fine line by giving some moody, heartbreaking lyrics a real pop accessibility, because on subject matter alone, this is the kind of record that could very easily just wallow in its own misery. Yet songs like the beautifully paced "I'm Not the Only One" and the skittering "Life Support" wear their emotions on their sleeves without resorting to mopey string sections. (Although make no mistake: String sections appear often here.) It's a well-balanced pop effort that has a specific point of view — a strong statement for an artist's debut album, nonetheless. Even if Smith is lonely, he would soon have Grammy Awards, and an Oscar, and more than a few platinum plaques to keep him company shortly after its release.

One of the most unassuming blockbusters in history, few could've guessed that a folk-affected jazz-pop album sung by Ravi Shankar's daughter would go on to become one of the best-selling albums of all time. Yet "Come Away with Me" hit at a perfect moment in a post-9/11 world, offering sweet relief with a series of songs that were modest in scope but lovingly rendered. Anchored by her smokey-smooth voice, Jones brought a set of new tunes penned by her ace music partners Jesse Harris and Lee Alexander to life (to say nothing of her own contributions, like on the dreamy title track), with her practiced delivery imbuing every word with meaning and emotion. "Come Away with Me" has seen its reputation fade away in recent years, but it remains an affecting, careful gem of a record that, if we're being honest, Jones never bettered. (To her credit, she changed her sound on each of her subsequent albums so much that it seems like she never even tried to recapture that moment.)

To put it simply, Joni Mitchell's output in the '80s was nothing more than a shadow of her generation-defining, sometimes confounding but always successful run of records in the '70s. For being a songwriter who married acoustic folk stylings to jazz idioms in fascinating ways, hearing Mitchell play around with synths and duets with Billy Idol wasn't anyone's idea of a good time. So for 1994's "Turbulent Indigo," Mitchell went back to the basics with acoustic guitar in hand. While not as dynamic as her legendary full-lengths "Blue" or "Court and Spark," "Turbulent Indigo" was nonetheless a return to form, with Mitchell lamenting over society's ills on tracks like "Sunny Sunday" and "Sex Kills" over some wise and wonderful chord changes. Yet by the time the liquid synths swoop in under her tender strums on "The Magdalene Laundries," it feels like we have recaptured a bit of that Joni magic that was missing for nearly an entire decade.

After absolutely obliterating all expectations for what a pop star was capable of with her sophomore album, "21," the anticipation for Adele's third record was so explosive that her opening sales week for "25" destroyed every record in existence, going triple platinum in a mere seven days — a feat that we're positive will never be broken again in our lifetime. At the end of the day, however, "25" doesn't hold the same cultural sway as "21" but is still a very, very good pop full-length. Opening herself to more mainstream concessions with tracks like "Send My Love (To Your New Lover)" and the striking "Water Under the Bridge," the ballads remain her strong suit, with the closing anthem, "Sweetest Devotion," and especially the lovely "When We Were Young" proving to be new touchstones for the world's favorite diva. Yet amid all the records and Grammy wins, "25" excels by going a bit out of Adele's established sound, with the percussive "I Miss You" even bordering on the sinister side of things. All we know is that we are still quite excited to see what Adele does next.

Kelly Clarkson's debut album, "Thankful," is a perfectly acceptable pop record, but given her fame came from a reality TV show, many doubted her credentials as a long-term musician and performer. With her follow-up, "Breakaway," however, the "American Idol" winner finally figured out the "sound" of Kelly Clarkson, which ended up being pop numbers that dressed and acted like rock songs. "Since U Been Gone," one of the greatest singles of the decade, will forever be her signature, but the bratty "Gone," the evocative "Behind These Hazel Eyes" and even the piano ballad "Where Is Your Heart" all sounded more like "Kelly Clarkson songs" than anything off her debut. Straight up and down, "Walk Away" still struts, "Because of You" remains an unmissable power ballad and, as an album, "Breakaway" is nothing short of a giddy Top 40 triumph.

When Taylor Swift referred to "1989" as her "first official pop album," some scoffed at such a declaration. Swift, if anything, though, is calculating, and her gradual embrace of decidedly non-country elements to her sound led her to this moment, and it's no wonder that the hits off of this album remain some of the most defining and popular of her career. While certainly not perfect ( "Welcome to New York" remains a bizarre opener), this record features radio staples like "Blank Space," the retro-leaning "Style," the thundering "Out of the Woods" and "Shake It Off" — her purest pop moment (well, second to the Deluxe Edition bonus track "New Romantics"). Even when she gets warm and synth-y on the Imogen Heap-indebted closer "Clean," it doesn't feel like a ploy, as Swift is smart enough to avoid "changing genre" and instead "evolving her sound" — and in the eyes of some, her sound was never better than on "1989."

While Lady Gaga's debut album, "The Fame," turned her into a star, looking back on it shows just how disjointed it was, with shoehorned guest spots and a swath of genre experiments that appear force-fed by the label. It was a hit regardless, but with "The Fame Monster," Gaga finally got to show the world her true artistic voice — and honestly, we're still reeling. From one of the best singles of the decade ("Bad Romance") to full-on Queen audio cosplay ("Speechless"), Gaga finally sounded in her element, capable of unleashing dance-pop songs so-dumb-they-were-brilliant ("Telephone") to spry little numbers that had a lot of bite ("Teeth"). In the minds of some monsters, "The Fame Monster" is Gaga's absolute artistic high point, and depending on the day, we might even be inclined to agree.

While 1996's "Mercury Falling" album was a critical miss for Sting, the former Police frontman was still very much playing to an aging boomer fan base that always made sure his records went platinum. Yet Sting was no dummy and could read the writing on the wall: Without reinvention, he truly would fade into obscurity. With that in mind, "Brand New Day" ended up surprising damn near everyone with its globetrotting but unmistakably contemporary sounds. "Desert Rose" became one of the decade's most hypnotizing sleeper singles in existence, and Stevie Wonder's harmonica practically takes a starring role in the uplifting title track, but the "Brand New Day" album cuts remain especially striking. The moody opener, "A Thousand Years," thrusts Sting into a new contemplative light, while the jazzy lover's lament "Big Lie Small World" works against all odds. Sure, Sting could still write anthems like nobody's business (see: "After the Rain Has Fallen"), but by the time the French rapper comes in during the beatnik lounge number "Perfect Love...Gone Wrong," it's clear that Sting has pulled off a truly radical artistic rebirth that is genuinely worth celebrating.

The drum beats roll like '90s hip-hop samples, and the horns and orchestrations evoke the best '70s soul singles, but that attitude — that's what separated Amy Winehouse from the rest of the pack. For her sophomore effort (and, tragically, her last album), the smart and sarcastic Winehouse worked with Mark Ronson, Salaam Remi and the Dap-Kings horn section to craft a stunning set of songs with a keenly nostalgic edge. "Rehab" was the big smash, but the soap opera-ready "You Know I'm No Good," sockhop lament over rapper Nas "Me & Mr. Jones" and the Ashford & Simpson-quoting "Tears Dry On Their Own" are truly transportive pop numbers, all stuffed with heartbreak and served with a swinging rhythm section. While losing Winehouse at such a young age will forever color our feelings about this long-player, we at least take solace in the fact that she went out with a bang, delivering a game-changing masterpiece of a record that's so often imitated but rarely, if ever, bettered.

There's a certain caste of people for whom the phrase "John Mayer's best album" means close to nothing, but for all of his controversial statements and questionable public choices, goodness gracious the kid could write some songs. Removed from the preciousness of his debut album, "Room for Squares," but before he got lost in the jam-band wilderness, "Continuum" is better than it has any right to be, with Mayer perfecting the solid, mid-tempo groove for a record that's built on regrets, heartbreak and faint hints of optimism. There's no overpowering radio concessions or fiery guitar solos here: just well-considered pop accented with just the right amount of blues. From the painfully honest groove of "I Don't Trust Myself (With Loving You)" to the soulful "Vultures" to the lovely acoustic number "Stop This Train" to the downtempo shuffle of "Slow Dancing in a Burning Room," "Continuum" is clearly, so obviously Mayer's best album that it's a shame that it hasn't come to define his career more than some of the donkey-headed statements to tabloids and press.

Adele's "21" arrived at a perfect moment, improving upon her winsome and promising debut in every way to become a four-quadrant hit, appealing to tastemakers and tweens, Top 40 listeners and people who still buy CDs — you name it. While part of that appeal can be traced to the back-to-back genre-span of her rock-tinged lead single, "Rolling in the Deep," and the tear-jerking ballad "Someone Like You," the rest of "21" still has far-reaching allure, from the thundering stomp of the take-me-back anthem "Rumour Has It" to the stop-start soul of "He Won't Go" to her perfectly picked cover of The Cure's "Lovesong." Some may poke holes in her lyrical conceits, but Adele more than makes up for it with her sheer vocal prowess, as that key-change in the chorus of "Someone Like You" still affects listeners every time they hear it. In an age of techno synths and SoundCloud trap beats, Adele's reign on radio felt like a true blast from the past, making many people nostalgic for a time when it was less about the producer behind the boards and more about that stunning, raw vocal talent.

When Madonna traces trends, her songs suffer under the weight of her own self-imposed commercial expectations. However, when she leans outside the mainstream to instead maybe start her own trends, she ends up with some of the most engaging pop music of any given era, and with her electronica reinvention on "Ray of Light," she rewrote the pop diva rulebook and changed the shape of what was acceptable on radio. While the title track is one of her all-time greatest anthems, "Ray of Light" truly is worthy of the Best Pop Vocal Album moniker because this, unquestionably, has Madonna's greatest vocal performances straight through. Having come off the musical "Evita," which required intense vocal training, she is looser and freer with her pipes here, and when paired with a wide range of songs, we end up getting every Madonna personality type rolled into a single, satisfying record. From playing it coy on "Candy Perfume Girl" to whispering her heartbreaks on "Frozen" to turning into the drum-and-bass diva we never knew we wanted in "Little Star," "Ray of Light" isn't only one of the best albums of the '90s, but it is also arguably Madonna's best record — full stop.

During the 10th Annual Grammy Awards, the category of Best Contemporary Album was conceived, soon shuttered and then left alone until its surprising mid-'90s revival, where it's now known as the award for Best Pop Vocal Album. It's a bit odd to rank a bunch of albums from the '90s and 2000s with a single entry from the '60s, and no offense to Madonna, but when you're ranking albums of a particular stripe and one of them just so happens to be The Beatles — you're putting The Beatles at No. 1. One of the earliest rock concept albums that just so happened to be embraced by the record-buying public, "Sgt. Pepper's" was the Fab Four's notorious band-inside-a-band gambit, affording the Liverpudlians a certain artistic freedom that they felt wasn't afforded in their prior configurations. Even if it sounds heady, the result is a record chock-full of songs that would help shape the entirety of pop music as a whole: "Getting Better," "With a Little Help From My Friends," "Lucy in the Sky With Diamonds" and the note-perfect closing suite of "A Day in the Life" — just to name a few. It was another masterpiece in a discography littered with masterpieces, and it's truly deserving of the title of Best Contemporary Album.