The Should-Be-Bigger Bracket: The Sweet Sixteen

Patrick Crowley
  

Tinashe vs. Sampha, Carly Rae Jepsen vs. Tegan and Sara, and more match-ups to help decide pop's most underappreciated artist.

Last week (Mar. 16), we kicked off the Should-Be-Bigger Bracket, our March Madness-style tournament between 32 artists who we feel have gone overlooked, to some degree, in the mainstream -- artists who, in our entirely subjective opinion, should have better sales, higher festival placement and radio play commiserate with their Internet adulation. We're going to use the next few weeks to determine which of them is the most underappreciated pop star of them all.

We narrowed our field of 32 to 16 last week, with upsets from Gallant (over Tove Lo) and Hey Violet (over MØ), and eighth-seeded Against the Current taking top seed Tinashe down to the wire. Today (Mar. 23), read on to find out who our edit team determined as the winners of our eight Sweet Sixteen matchups.

 

(1) TINASHE VS. (4) SAMPHA

Taylor Weatherby: When it comes to having a unique voice, Sampha stands out amongst his competition a little more than Tinashe, who could at least find logical comparison among the likes of Kehlani and Jhene Aiko. But when it comes to making music that make people want to turn up their speakers and bust a move, Sampha hardly has anything on Tinashe’s catchy beats and belt-along moments. WINNER: TINASHE

Xander Zellner: I’m fairly confident that both of these artists have superstar potential, but Sampha is something else entirely. His soulful R&B vocals combined with synth-y beats are unrivaled, and other superstar hitmakers are beginning to take notice. If his feature on Drake’s More Life is any indication, Sampha should hopefully be a mainstream success in no time. VERDICT: SAMPHA

Adelle Platon: Beyond slumber parties with Britney Spears and penning pop smashes for the likes of Jennifer Lopez and Fifth Harmony, Tinashe's solo track record is sprinkled with sex appeal and infectious hooks. Team no sleep can rally for the singer's around-the-clock work ethic, too. Just hit play on her recently released Nightride mixtape. VERDICT: TINASHE

Chris Payne: I adore Sampha’s voice, purchased his LP, and could totally see it creeping onto my top 10 list when 2017 is through. But at this point in the bracket, we really gotta start thinking of who’s really trying to get hits, and who’s more suited for the critical acclaim lane, with some Drake guest spots tossed in. That would be Sampha, especially after More Life put his voice in the ears of approximately all the teens over the weekend. On the other hand, Tinashe was a one seed for a reason. She showed up outside the Billboard office last week on a fire truck with a flash mob of firefighter-costumed male strippers. Get her to the next round. VERDICT: TINASHE

Andrew Unterberger: No shame for Sampha, who's as ascendant a talent as we've seen in the pop realm the last few years, but even the singles that have slipped through the cracks in between, Tinashe full-lengths had more commercial potential than his defining jams. There may come a day where Sampha should be better -- though Tinashe won't give up that ground easily either -- but unlikely that he ever should be bigger. VERDICT: TINASHE
 

WINNER: TINASHE
 

(3) BETTY WHO VS. (7) GALLANT

Jason Lipshutz: Here’s a fun exercise: go through Betty Who’s 2014 debut Take Me When You Go and rank every song. Guaranteed that the 10th-best song on your list (“Missing You,” maybe? Or “Alone Again”?) is more accomplished than most singles currently dominating Top 40 radio. Betty moves on. VERDICT: BETTY WHO

Joe Lynch: With a falsetto that makes knees weak and a live show that will turn anyone into a believer, Gallant is the most criminally slept-on R&B singer around. VERDICT: GALLANT

Dan Rys: Gallant is such a singularly magnetic talent that, in my mind, it's about when he becomes an international star, rather than if. He's already shared stages with Elton John, Seal and Sufjan Stevens and picked up a Grammy nomination for his debut album Ology; once the masses catch up, he'll already be gone into the stratosphere (and the current alt-R&B wave should help him, too). It's all there -- what are y’all waiting for? VERDICT: GALLANT

Andrew Unterberger: Listened to "You're in Love" or "Runaways" recently? Until Katy Perry's opening for her, this is Betty's bracket to lose. VERDICT: BETTY WHO

Chris Payne: I voted for both Betty and Gallant in round one, so I thought long and hard with this one. Gallant deserved more attention behind his studio debut album last year, but Betty — currently rolling out her sophomore effort — is further along in her career and at this juncture, in more dire need of that radio song. Her 2014 debut Worlds Apart was an awesome pop EP, and full-length Take Me When You Go was just as good, but both were so slept on commercially that The Valley (out this Friday, by the way) might be her do-or-die moment. Verdict: BETTY WHO


WINNER: BETTY WHO
 

(1) CHARLI XCX VS. (5) LIZZO

Lyndsey Havens: Charli XCX is a seasoned artist by now with two albums under her belt and the recent release of her mixtape, not to mention her collaborations with the likes of Iggy Azalea, Lil Yachty, Ty Dolla $ign and more. Meanwhile, Lizzo is primarily riding the wave of one breakout hit -- catchy as it may be. VERDICT: CHARLI XCX

Jason Lipshutz: Shout-out to Lizzo, who absolutely should be bigger and no doubt will be someday soon, but Charli XCX boasts two of the most thrilling pop albums of the decade and dropped a damn good mixtape in the midst of this bracket challenge, as a subtle reminder that any challengers best come correct. VERDICT: CHARLI XCX

Taylor Weatherby: If you’re looking for two female singers who are a physical representation of attitude, Lizzo would be a great hip-hop and soul example and Charli XCX makes for a sassy pop prototype. They’re both badass in their own right, but Charli has already landed a song in the top 10 of the Hot 100 as a lead artist – let another diva like Lizzo have her time in the limelight. WINNER: LIZZO

Chris Payne: Okay, this one’s a little easier. “Good As Hell” and “Phone” are jams, and I like where she’d headed, but she hasn’t been slept on commercially nearly as much as Charli, who hit the scene all the way back in 2011. Two albums full of potential smashes and she’s only seen hits because of Iggy Azalea and “The Fault In Our Stars”? Come on. There’s no one-seed upset here. Verdict: CHARLI XCX

Andrew Unterberger: The second round is a fair exit point for Lizzo at the moment, so I'll just use this opportunity to say that Charli's Number 1 Angel is my favorite thing she's done since True Romance and deserves as much attention as that other stopgap, don't-call-it-an-album major release of the last few weeks. VERDICT: CHARLI XCX
 

WINNER: CHARLI XCX
 

(3) SKY FERREIRA VS. (2) JOJO

Jason Lipshutz: Sky Ferreira’s “Everything Is Embarrassing” was correctly hailed as a pop mini-masterpiece upon its release in 2012. The following year, she dropped two songs, “You’re Not the One” and “I Blame Myself,” that were arguably better. For comparison’s sake, JoJo’s Mad Love comeback boasted some rhythmic treats but nothing as rousing as “Leave (Get Out).” Sadly, she will have to follow the advice of her signature hit's title here. VERDICT: SKY FERREIRA

Andrew Unterberger: Should JoJo be bigger? Probably, but any number of former teen stars that haven't gotten a fraction of the album sales, attention or general adoration that JoJo's gotten in recent years would probably say she's doing just fine. Meanwhile, Sky Ferreira is a former teen star that never really was, her pre-switchup pop fare being good enough to make her a sensation, but never quite crossing her over. Regardless of whether or not she should currently be bigger, her bigness from those days is still overdue. VERDICT: SKY FERREIRA

Katie Atkinson: In my mind, JoJo is still the patron saint of this bracket. Sure, she already had a taste of the pop upper echelon with "Get Out (Leave)" and "Too Little Too Late," but neither took her over the line that she so deserves to cross. Let's get her there! VERDICT: JOJO

Taylor Weatherby: There’s absolutely nothing wrong with what Sky Ferreira is all about: Edgy, pop-driven grooves that highlight her smooth tone and make you want to bop along. But if JoJo were to do the same thing, she would add some diva flair (in the form of sporadic belt-outs) that would be simply irresistible to sing along with – or make you forget all about Sky’s stuff. WINNER: JOJO

Xander Zellner: While I love JoJo’s comeback story and several tracks off Mad Love, the singer seems to already be a household name -- in part thanks to her two albums from way-back-when and because she’s been touring every year (with the exception of 2014) since 2010, including openings gigs with Joe Jonas and Big Time Rush. Simply put, it feels wrong to say an artist “should be bigger” when said artist has three top 10 albums on the Billboard 200. Ferreira, on the other hand, hasn’t even been given a shot at radio play despite having at least three songs that should be smash hits on Top 40. VERDICT: SKY FERREIRA
 

WINNER: SKY FERREIRA
 

(1) CARLY RAE JEPSEN VS. (5) TEGAN AND SARA

Lyndsey Havens: I, personally, find this comparison offensive. Sure, Carly Rae Jepsen proved the naysayers wrong with her highly praised pop album, 2015’s Emotion, but she also rose to fame due to one viral hit in 2012 -- you know the one. Tegan and Sara have not only been around for nearly two decades, but continue to reinvent their sound on each and every album, proving their staying power is far more… powerful. VERDICT: TEGAN AND SARA

Jason Lipshutz: Just an absolutely brutal matchup between a pair of unassailable pop acts. But… have you checked the current sales of Emotion? For as much as Carly Rae Jepsen is Queen of The Blogosphere, she is no longer Queen of Album Equivalent Units, no matter how many Justin Bieber and Tom Hanks cameos she can squeeze into music videos. Tegan and Sara should be bigger too, but at least they’re playing festival main stages. CRJ deserves a world far greater than the one she inhabits. VERDICT: CARLY RAE JEPSEN

Andrew Unterberger: A heartbreaker for sure, but you have to feel like Tegan and Sara themselves would stump for Carly Rae here, don't you? Besides, their Heartthrob essentially set the blueprint for Emotion, so a win for Carly is kind of a win for them anyway. VERDICT: CARLY RAE JEPSEN

Joe Lynch: Carly Rae Jepsen is the making the catchiest, smartest pop right now – period. She should be notching No. 1s left and right. VERDICT: CARLY RAE JEPSEN

Katie Atkinson: This is a tough one, because both acts deserve to reach new heights of pop. But 2015's Emotion album, and its unjustifiably lackluster reception, proved that Carly Rae deserves bigger and better things. Call her back up to the big leagues (maybe). VERDICT: CARLY RAE JEPSEN
 

WINNER: CARLY RAE JEPSEN
 

(6) JIDENNA VS. (2) VINCE STAPLES

Xander Zellner: Jidenna has crafted some stellar tracks over the past couple years, but Vince Staples has been consistently releasing music for almost 10 years, to no avail. He, deservedly, should be on the same commercial level as his past collaborators Mac Miller and the Odd Future crew by now. VERDICT: VINCE STAPLES

Joe Lynch: With a Janelle Monae cosign and a genre-blurring debut, it's a good bet that we've only scratched the surface of what Jidenna can do. VERDICT: JIDENNA

Dan Rys: This is admittedly a tough one -- they both should be qualify -- but Staples deserves to go through due to the clarity of his vision and the directness with which he delivers it. Jidenna certainly has a well-defined aesthetic and message; the trademark suits and overall message are clearly well-thought-out and considered. But musically, there's a sense that he's still figuring out where he wants to go and how to get there, whereas Staples has no such reservations. Few artists have identified and owned a lane as thoroughly and completely as Vince has, and while it isn't necessarily one that the mainstream tends to embrace, he should be rewarded for it. VERDICT: VINCE STAPLES

Chris Payne: I still have to listen to Jidenna’s new album, and that’s on me. Still, I get that he’s a lot more than “Classic Man.” Vince Staples, though. Summertime 06 sounded like a classic the second it dropped and as Andrew pointed out in round one, Kendrick Lamar has recently proven that a hip-hop record without a radio hit can indeed become a cultural phenomenon. Vince needs his due. VERDICT: VINCE STAPLES

Andrew Unterberger: Vince rating former GQ Men of the Year is still more essential than anything Jidenna's ever done on record -- except maybe for "Bambi," that song is awesome. Still. VERDICT: VINCE STAPLES
 

WINNER: VINCE STAPLES
 

(1) LITTLE MIX VS. (4) BLEACHERS

Lyndsey Havens: Little Mix won The X Factor in 2011 and have been churning out bubblegum pop ever since. Bleachers’ frontman, Jack Antonoff, has meanwhile been gearing up to take the industry by storm as he just worked with Lorde, played SXSW and is currently recording the versatile alt-pop group’s anticipated sophomore album. VERDICT: BLEACHERS

Joe Lynch: The world is big enough for two girl groups, and with Fifth Harmony becoming top 10 hitmakers, it's about time this British quartet start getting U.S. radio play with their frothy pop pleasures. VERDICT: LITTLE MIX

Taylor Weatherby: Considering these two groups literally sound absolutely nothing like each other and they’re both pretty great, this makes for quite the challenging match-up. In their respective sectors of pop, both Little Mix and Bleachers are standouts thanks to their anthemic, catchy tunes. But when you focus strictly on vocal ability, the British girl group soars ahead of Jack Antonoff and his band – and frankly, also ahead of just about everyone in the pop music game. Long live their girl power. WINNER: LITTLE MIX

Andrew Unterberger: Gotta say, I listened to Strange Desire for the first time in a couple years in between our first two rounds, and now I sorta regret not voting for Bleachers last week -- fun, explosive, clever and boundlessly creative album. Well, better late than never. VERDICT: BLEACHERS

Katie Atkinson: Jack Antonoff is doing just fine for himself, between producing much of Lorde's highly anticipated next album and that little side project he has in the chart-topping band Fun. But Little Mix are poised and ready for their "Work From Home"-level breakout hit (or hell, at least "Worth It" level). VERDICT: LITTLE MIX
 

WINNER: LITTLE MIX
 

(6) HEY VIOLET VS. (2) KACEY MUSGRAVES

Joe Lynch: With two albums under her belt, Kacey was a favorite for 'best country album of the year' lists in 2013 and 2015 but she hasn't scored a crossover smash – yet. But don't be surprised if album number three sees the Texas singer-songwriter break through. WINNER: KACEY MUSGRAVES

Taylor Weatherby: While Hey Violet may seem like they’re pretty new to the music scene, think again: The group’s female members are nearly a decade in. After starting out performing hard rock in the all-girl band Cherri Bomb, the ladies recruited two dudes and have reinvented themselves in the pop-punk realm they had been searching for – successfully so, recently landing a single on the Hot 100. Edgy country gal Kacey may have done that twice, but the 28-year-old is also 10 years senior to Hey Violet’s lead singer Rena Lovelis… even she would have to give kudos to the catchy band of youngsters. WINNER: HEY VIOLET

Katie Atkinson: This is a no-brainer for me: Kacey Musgraves needs to channel some of the mainstream mojo of fellow country divas Kelsea Ballerini and Maren Morris and take one of her quirky, classic-country-inspired songs to the top of the Nashville charts. VERDICT: KACEY MUSGRAVES

Xander Zellner: Kacey Musgraves is great! And her pair of No. 1 country albums and Grammy Awards prove that she’s already an A-lister in the country realm. However, Hey Violet is bringing some much-needed pop-rock to Top 40 music that we haven’t seen in a while. Hopefully we don’t have to wait much longer for a follow-up to “Guys My Age,” which only made it to No. 68 on the Hot 100. VERDICT: HEY VIOLET

Chris Payne: I like Kacey as much as the next critic (which means a lot, TBH) but can we just come out and say Pageant Material was kinda middle of the road? Squabbles with country radio aside, she’s gotten great looks from the mainstream media (Grammy shine, magazine covers, a Katy Perry co-sign) that Hey Violet so badly deserves. Verdict: HEY VIOLET
 

WINNER: HEY VIOLET


Check back tomorrow for our Elite Eight matchups!