The Should-Be-Bigger Bracket: 32 Artists Square Off for the Honor of Pop's Most Underappreciated Star

The Should-Be-Bigger Bracket: 32 Artists Square Off for the Honor of Pop's Most Underappreciated Star

March Madness is officially upon us, and while college basketball's marquee tournament will eventually see its field whittled down to the heavy hitters, everyone knows what the event is really all about in its first few weeks -- the underdogs. You want to see the squads that everyone has written off (or underrated, or never heard of in the first place) rise up and triumph over the front-runners, the A-listers and the established perennials.

We here at Billboard are taking this opportunity to salute our own pop Cinderellas: a pool of 32 artists -- think of them as the potential upset picks for pop's overall field of 64 -- who we feel have gone overlooked, to some degree, in the mainstream. And we're going to use the next few weeks to determine which of them is the most underappreciated pop star of them all. We present: The Should-Be-Bigger Bracket.

Now of course, we're not saying all these artists are as obscure as Jacksonville State and Northern Kentucky -- some of them have had tremendous runs in the past, and most of them have devout, even rabid fan bases. But we love all of these artists at Billboard, and we feel they haven't gotten their proper due outside the confines of the Pop Internet. They've had one or two crossover hits when they should have had a dozen by now. They've had mixtape success, but they should be going platinum. They're playing festivals, but they should be headlining them. They, quite simply -- in our entirely subjective, unscientific opinion -- should be bigger.

So we'll be squaring off these 32 artists over the next few weeks in one-on-one, NCAA tournament-style competition, with our crack edit team casting their votes in each round to determine who advances to the next round. We'll do eight of our 16 first-round competitions today, and eight tomorrow. But before we get into that, let's introduce our 32 teams -- since, if you all already knew who all of them were, there would be no point in doing this in the first place.

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ONE SEEDS:

Tinashe: Irresistibly genre-blurring singles and a future-classic full-length, but just one Top 40 crossover to date.

Charli XCX: Dynamic and innovative shape-shifter, had misfortune of giving her biggest solo hit to The Fault in Our Stars.

Carly Rae Jepsen: Unquestioned queen of pop blogs, radio still waiting for the next "Call Me Maybe."

Little Mix: British girl group as big as Fifth Harmony in home country, U.S. mainstream yet to catch up.

TWO SEEDS:

Tove Lo: "Habits (Stay High)" was a rightful left-field smash, multiple Lady Wood singles were just as alluring.

JoJo: Made successful transition from teen TRL fav to pop cult hero, your mom still only knows "Leave (Get Out)."

Vince Staples: Critically adored and Internet-irresistible, dude should be headlining Coachella by now.

Kacey Musgraves: Cool enough to be The Fader's first country cover star, but her biggest chart hit was performed by Miranda Lambert.

THREE SEEDS:

Betty Who: Big enough to soundtrack viral videos and top club charts, rest of the world still reads her name with a question mark.

Sky Ferreira: Underground star closed the door on her early dalliance with Top 40, may not even want to be that much bigger.

Dawn Richard: Danity Kane alum makes some of the most challenging pop right now -- too challenging for the mainstream, thus far.

: Several flawless electro-pop singles, but none on the Hot 100 without Major Lazer or Iggy Azalea's name first.

FOUR SEEDS:

Sampha: Collabs with Drake and Solange preceded a stellar 2017 debut LP, his own headliner status remains uncertain.

Years & Years: Blockbuster U.K. success and an unofficial Zac Efron co-sign, but no U.S. top 40 smashes just yet.

Christine & the Queens: French art-pop sorceress has conquered Europe, will her rule extend Stateside?

Bleachers: Jack Antonoff scaled pop's highest highs writing for and with others, his own project has peaks yet to reach.

FIVE SEEDS:

Marina and the Diamonds: Established cult and festival favorite, still lacks That One Song to make her a household name.

Lizzo: Prolific and versatile talent, Barbershop: The Next Cut single "Good As Hell" should've owned last summer.

Tegan and Sara: Indie icons, and your favorite pop star's favorite not-quite-pop stars since targeting the mainstream two albums ago.

Nao: Commercial syncs and critical acclaim have yet to lead to mainstream visibility.

SIX SEEDS:

Vic Mensa: As gifted and promising as his name implies, the Kanye-approved MC has yet to capture headlines like his mentor.

Sevyn Streeter: "It Won't Stop" was the most undeniable of her beguiling R&B singles, but radio still required a Chris Brown verse before playing it.

Jidenna: Surprise hit "Classic Man" got treated as novelty, while chameleonic debut LP The Chief proved he deserves better.

Hey Violet: "Guys My Age" was too edgy and brilliant a rock crossover to be kept off the Hot 100, but No. 68 is still as high as it's gotten.

SEVEN SEEDS:

Gallant: Debut Ology was intriguing enough to draw a Grammy nod, he should be performing at the ceremonies in a couple years' time.

K.Flay: Longtime indie rapper has set her sights on the rock mainstream, "Blood in the Cut" was a hell of a first strike.

Maggie Rogers: New York singer-songwriter went viral enrapturing Pharrell, rest of U.S. may be on verge of similar bewitching.

Andrew McMahon: Something Corporate and Jack's Mannequin frontman has yet to rise above cult stardom, enthralling pop solo work may represent his best shot yet.

EIGHT SEEDS:

Against the Current: Explosive pop-punk band courting the mainstream's fringes, yet to really rocket onto charts.

Shura: Nothing's Real was among 2016's best pop LPs, though far too few people outside the blogosphere noticed.

Kelela: "Rewind" was just named one of NYT's 25 songs telling us where pop is going, tellingly, the song came out in '15.

St. Lucia: Just wait 'til their muscular brand of synth-rock finds its way to the right movie montage.

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Got it? OK, get in your appropriate cheering section, check out our Spotify playlist of all the artists involved below, and let the true March Madness begin.

(1) TINASHE VS. (8) AGAINST THE CURRENT

Adelle Platon: Against The Current’s rebellious In Our Bones LP packs many fine young-and-wild anthems. Still, Tinashe’s sultry, weed-induced hits a la “2 On,” which landed a remix from Drake, and “Party Favors” hold more gravity. VERDICT: TINASHE

Xander Zellner: Against the Current brings an unparalleled pop-punk energy to their debut album -- last year’s In Our Bones -- that I haven’t heard since Paramore. VERDICT: AGAINST THE CURRENT

Andrew Unterberger: Like few other artists in this bracket, Tinashe’s a true triple-threat, and as effective on ecstatic radio singles as she is on hypnotic nocturnal mixtape ballads. Here’s to perpetually hoping her next project is the one that’s going put her permanently on top. VERDICT: TINASHE

Chris Payne: I’ve straight up told people from Against the Current and Paramore’s label, “Wouldn’t it be great if Paramore took them out on tour?” -- so yeah, there wasn’t really much in this bracket, or any bracket for that matter, that was going to get me to not vote for these kids. Tinashe’s been on a handful of familiar songs between her own stuff and fancy features, whereas ATC is relatively unknown to those who aren’t dialed into the Warped Tour/Alternative Press scene. They’re a rock band that can channel “Misery Business” or Katy Perry’s “Roar” onstage; crossover status should be theirs. VERDICT: AGAINST THE CURRENT

Joe Lynch: Tinashe's Aquarius came out in 2014, and even though the proper follow-up still isn't on the calendar, fans and critics can't stop talking about it. That kind of lasting excitement is rare in the online era. VERDICT: TINASHE

 

WINNER: TINASHE

 

(4) SAMPHA VS. (5) MARINA AND THE DIAMONDS

Jason Lipshutz: Sampha's Process album is equal parts loss and euphoria, and makes good on years of hype. That said, Marina Diamandis has been making good on her early singles for years, and can command rooms (which should be larger) better than most pop artists. VERDICT: MARINA AND THE DIAMONDS

Adelle Platon: British songbird Marina and the Diamonds’ latest full-length Froot is ripe with edgy pop songs but, Sampha’s Process feeds the soul with consecutive rounds of hearty alternative R&B. VERDICT: SAMPHA

Andrew Unterberger: Marina's sensational, but I'd be lying if I said any one of her shimmering synth-pop crystals ever affected half as much as even the first minute of "(No One Knows Me) Like the Piano." VERDICT: SAMPHA

Katie Atkinson: Sampha has serious star power on his side, writing and providing vocals for Kanye, Drake, Frank Ocean and more, but it's time for the U.S. to fully embrace what the U.K. has known for eight years: Marina Diamandis is flawless. VERDICT: MARINA AND THE DIAMONDS

Lyndsey Havens: Marina and the Diamonds deliver synth-soaked bangers -- some of which are memorable. Sampha, on the other hand, relies lightly on synths, allowing his soulful vocals to take a front seat, and resulting in whole album worth of songs that stick with you permanently. VERDICT: SAMPHA

 

WINNER: SAMPHA

 

(3) BETTY WHO VS. (6) VIC MENSA

Jason Lipshutz: Love Vic and “Down On My Luck” especially, but Betty Who’s 2014 debut Take Me When You Go was filled with immaculate hooks built around a wholly charming personality. The pun is too easy here: no, Betty, somebody loves you. VERDICT: BETTY WHO

Dan Rys: I don't even know how else to say it, but when Vic Mensa is on point, he's one of the most dynamic and riveting artists and performers of his generation. Look, don't ask me where his debut album is, or why we've only gotten 10 new Vic songs since his 2013 project Innanetape. He should be huge by now, but somehow, he just isn't yet. VERDICT: VIC MENSA

Lyndsey Havens: In June of 2016, Betty Who delivered an electropop cover of “I Love You Always Forever.” Also in June of 2016, Vic Mensa dropped the powerful track “16 Shots” that sees the Chicago bred, Grammy-nominated MC ask: “Shot 'em 16 times, how f--ked up is that?” Another valid question: Is there really any competition? VERDICT: VIC MENSA

Taylor Weatherby: Creating an earworm is definitely a different beast for a synth-pop artist versus a rapper. But when pitting Betty Who’s glittery ‘80s vibe and melodies (that are catchy AF) up against Vic’s all-over-the-map style, Betty has the upper hand on this one. VERDICT: BETTY WHO

Andrew Unterberger: Last year's There's Alot Going On EP from Vic Mensa was a little more promising than the singles we've heard from Betty Who's upcoming second album, so maybe this switches in a year or two. But when the dust settles on the mid-'10s, there might not be five pop albums more perfect than Betty's Take Me When You Go, which should've had Katy Perry opening for her, not the other way around. VERDICT: BETTY WHO

 

WINNER: BETTY WHO

 

(2) TOVE LO VS. (7) GALLANT

Adelle Platon: Gallant is an R&B savant who can sing the roof off of any soundscape his crisp vocals touch. Whether gliding on dubstep-tinged beats or futuristic slow jams, his falsetto commands your full attention. VERDICT: GALLANT

Jason Lipshutz: Tove’s confessional pop hit a new level of combustibility on last year’s sorely overlooked Lady Wood. Gallant and his heavenly pipes scream promise, but seriously, have you heard “Keep It Simple”?! VERDICT: TOVE LO

Katie Atkinson: Gallant outdid himself with debut album Ology (and scored the Grammy nomination to prove it), but I'm giving this one to Tove based on the underappreciated perfection of "Cool Girl" alone. VERDICT: TOVE LO

Dan Rys: Have you seen this kid perform live? He's a goddamn superstar. No studio gymnastics can touch the raw power of his unaltered voice. VERDICT: GALLANT

Chris Payne: Does Tove Lo really belong in this bracket? Two very real hit songs from the not-too-distant years of 2014 and 2015 is enough for me, even if last year’s Lady Wood was underappreciated. If she never rises above playing the second-to-last set on the second biggest stage at Coachella, that’s not exactly going to keep me up at night. But from the moment I saw Seal belt along with Christopher Gallant at Coachella last year, I was along for the ride, with follow-up listens of Ology and a proper theater show confirming the pop world’s been sleeping. Give this guy some more attention. VERDICT: GALLANT

 

WINNER: GALLANT

 

(1) CHARLI XCX VS. (8) SHURA

Jason Lipshutz: Shura may be the unofficial leader of Dreamy ‘80s Technicolor Pop’s new school, but this is like bringing a knife to a gun fight. Charli has been on three Top 10 hits on the Hot 100 and STILL should be way bigger. VERDICT: CHARLI XCX

Xander Zellner: Charli XCX has been a part of some of the best pop smashes of the decade’s first half (see: “I Love It” with Icona Pop, “Fancy” with Iggy Azalea, and of course, “Boom Clap”), but despite not being as chart-crashing, plenty of gems from more recent efforts like Sucker and the Vroom Vroom EP deserved to be nearly as big. Even for just those three songs, though, this would be a no-brainer. VERDICT: CHARLI XCX

Chris Payne: I love both of these British ladies, so to make my decision, I really broke down the meaning of “Should Be Bigger.” Charli’s already had a nice career — plenty of cool looks and critical acclaim, to go along with a couple big hits, counting “Boom Clap” and her guest spot on “Fancy.” She should be bigger, but how much bigger? Like, 3.5 hits instead of 1.5? An album that sold a little more? Shura’s whirlwind John-Hughes-synthpop-made-for-2016-debut Nothing’s Real is better than any Charli album and she’s had about 5 percent of the attention stateside. VERDICT: SHURA

Lyndsey Havens: Shura honed her songwriting skills during her gap year in the Amazon. Meanwhile, Charli XCX cut her teeth performing at warehouse raves in London -- and it shows. VERDICT: CHARLI XCX

Andrew Unterberger: Shura’s Nothing’s Real debut LP from last year is an overpowering collection of perfect pop songs. Charli’s got about three and a half of those already. VERDICT: CHARLI XCX

 

WINNER: CHARLI XCX

 

(4) YEARS & YEARS VS. (5) LIZZO

Adelle Platon: Blending Beyonce-levels of confidence (“Scuse Me”) with meme-worthy realness (“Phone”), Lizzo’s razor-sharp yet comedic bars deserve worship hands in the air. VERDICT: LIZZO

Andrew Unterberger: For a song that never cracked the Hot 100, Years & Years' "King" has shown impressive legs, racking up nearly a quarter-billion Spotify plays and presaging big things to come for the U.K. trio stateside. But Lizzo should've been a star for some time now -- not many pop artists have the personality to make a shaggy-dog joke like "Phone" not only likable, but damn near irresistible. VERDICT: LIZZO

Katie Atkinson: t's hard to disagree with both Andre 3000 and (especially) with the late great Prince, but even though both raved about body-positive rapper Lizzo, the U.K. has it right (again) in its support for electronic trio Years & Years. VERDICT: YEARS & YEARS

Lyndsey Havens: Lizzo sings the sassy truth on “Good as Hell,” a catchy track that can be played thin. Years & Years rather covered all bases on hit “Desire,” with a co-signed version from Tove Lo and an infectious remix from Gryffin. Something for everyone. VERDICT: YEARS & YEARS

Joe Lynch: Years & Years is an alluring British electronic trio, but the Minneapolis-based rapper Lizzo very well may be the future of hip-hop to come. VERDICT: LIZZO

 

WINNER: LIZZO

 

(3) SKY FERREIRA VS. (6) SEVYN STREETER

Adelle Platon: Sky’s the limit for Sevyn Streeter, who has written for the likes of Alicia Keys and Ariana Grande, but keeps her own material on the sexier side of R&B, with unfiltered love songs fit for breakups and the bedroom. VERDICT: SEVYN STREETER

Xander Zellner: Ferreira’s Night Time, My Time, her debut album from 2013, is the perfect mix of synth-pop mixed with indie rock. Here’s to hoping her upcoming sophomore album Masochism launches her into the mainstream. VERDICT: SKY FERREIRA

Andrew Unterberger: Sky Ferreira might be the closest thing the 2010s have to a '90s style alt-rock superstar, even though (or maybe because) her music carries virtually no obvious influence from any Clinton-era megabands. Sevyn Streeter's probably already had a bigger chart hit than Sky ever will, but what the latter's going for just feels more indelible. VERDICT: SKY FERREIRA

Chris Payne: You can absolutely say that Sevyn has been trying for a hit more than Sky Ferreira. Honestly, I’ve been trying for Top 40 airplay more than Sky Ferreira. That doesn’t change the fact that 2013’s Night Time, My Time is a dazzling update on new wave that’s aged incredibly well, considering October 2013 is pretty much a decade and a half in internet time. VERDICT: SKY FERREIRA

Joe Lynch: Sevyn Streeter is criminally underrated, but the fact that radio hasn't afforded Sky Ferreira the chance for a radio hit should be punishable by up to seven years in prison. VERDICT: SKY FERREIRA

 

WINNER: SKY FERREIRA

 

(2) JOJO VS. (7) K.FLAY

Jason Lipshutz: Ignore the tortured label history, and set aside the (still-great) throwback tracks like “Too Little Too Late” and “Leave (Get Out).” The fact is, JoJo has a voice that blows one away in a live setting, and deserves to be playing much bigger venues now that her comeback is complete. K.Flay is great! But her bid here is too little, too la-- [falls off cliff] VERDICT: JOJO

Xander Zellner: The multifaceted, genre-bending K.Flay is unlike anyone else in this bracket. She fuses alternative with hip-hop to create a sound that’s dark, edgy and, well, different. Is she a good fit for pop radio? We'll see. But her 2014 debut album Life as a Dog is certainly worth your time, and her upcoming follow-up Every Where Is Some Where could be even better. VERDICT: K.FLAY

Taylor Weatherby: In the era of Auto-tune, there’s something to be said about a pop singer who actually has the vocal vigor to back up their material. K.Flay’s edgy vibe and croaky voice offers a unique sound, but JoJo established her powerhouse prowess more than a decade ago – and further demonstrated that with her comeback LP Mad Love, which is even more impressive than her early records. VERDICT: JOJO

Andrew Unterberger: Secretly, K.Flay's been around as long as JoJo -- both released their debut projects in 2004 -- but while the long-overdue latter's pop comeback feels like making good on the sins of the past, the former's thrilling, genre-muddying ascent truly feels like the future, and is even more exciting as a result. VERDICT: K.FLAY

Katie Atkinson: Sorry, K.Flay, but JoJo epitomizes everything this bracket stands for: An artist with huge talent and incredible songs who just can't turn her level of online adoration into similar mainstream recognition. VERDICT: JOJO, ALWAYS AND FOREVER

 

WINNER: JOJO

 

Check back tomorrow (Mar. 17) for the results of the other eight first-round matchups.

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