Is Justin Timberlake the Best Male Pop Star of the 21st Century? (Staff Debate)

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Justin Timberlake performs after the second dress rehearsal for the Eurovision Song Contest final in Stockholm on May 13, 2016.

With Justin Timberlake set to release his fourth album -- or fifth, depending on how you gauge The 20/20 Experience -- this Friday (Feb. 2), two days before he takes the stage at Super Bowl LII, it's a good time to size up JT's overall musical resume and ask: Is he the best male pop star of the 21st century?

Six Billboard staffers exchanged their thoughts on the subject, which you can read below. 

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Andrew Unterberger: OK, so first off -- I wanted to kinda lay out the 21st century male pop stars who I feel like have the chips to buy in at this table. The combination of skills, longevity, crossover appeal, hits, and general iconicity, if that's even a word. And I'd say that taking all of that into account, these are the eight guys we're talking about (in alphabetical order so not to be prejudicial): 

Justin Bieber
Drake
Eminem
Lil Wayne
Bruno Mars
Justin Timberlake
Usher
Kanye West

Of course, some of these are rappers whose status as pop stars could be considered arguable -- lord knows we had plenty of arguments about this when figuring out eligibility for our Best Deep Cuts by 21st Century Pop Stars list a couple months ago -- but who I feel spent enough time at pop music's center to at least be in the discussion. You can decide for yourself whether or not you agree. 

Anyway, of those eight, I'm gonna go with the guy who maybe has the least contemporary clout: Usher Raymond IV. We forget about Usher a lot when discussing the greats of this century -- but why? Aside from JT and Eminem, he's the only guy on that list that's been a star since century's beginning, and at the time, his production was absolutely unfuckwithable. He began the century with two near-masterpieces in 8701 and Confessions (which sold a combined 14 million copies and spun off six Hot 100 number one hits) and though he's been less consistent since, he's still good for at least one absolute knockout single every couple years -- and for my money, 2012's Looking 4 Myself is still his best album, front to back. 

And the thing that really gives him over the edge over Timberlake for me is that he's allowed us to see him at his absolute messiest. He's undergone just about every public drama a celebrity can -- romantic, familial, legal -- and he's put all of it into his music, too, which can be uncomfortably personal at times ("Papers," anyone)? Ross and I were talking the other day about how JT doesn't have a song as good as "Climax," but more importantly, he's never even attempted one: Justin's too cool, too composed for that, which is fine, but not necessarily what I want from my pop stars. Throw in Usher's formidable singing and dancing abilities, and his ease of evolution from the JD era in pop to the Neptunes era to Lil Jon to David Guetta to Diplo, and he's my guy for this, easy.

Chris Payne: Dang, I think you did a good job of arguing one of the tougher sells on that list. When you initially floated this idea, I was thinking how Usher's near-20-year run of Hot 100 hits (circa 1997 - circa 2014) is so damn impressive and underrated. But I just can't give this title to someone who it seems has fallen off, critically and commercially, in the current moment and just isn't coming back. The only thing making us remember Hard II Love is that terrible album art. 

When I close my eyes and think of what male pop star has defined culture since I graduated middle school, I think of Drake. Even through the nine years before "Best I Ever Had," it still feels like he was.... there. The texture and sentiment of his music, the token Drake-ness, was living and breathing in popular music for a while. He just embodied it as one person, and then took it in many different directions: the rapping, the singing, pulling off both at the same time so well that it became standard, and also re-defining the norms rappers are held to through his beefs and his vulnerability. Simply counting MCs as pop stars feels so much more natural now since he arrived. Kanye laid a lot of the groundwork for this and I personally love him a lot more, but right now this title is Drake's.

Ross Scarano: I'm with Major Payne. One way I think about stardom is through novelty and influence. Ultimately, Justin Timberlake is a student of Michael Jackson. It wouldn't be correct to describe someone as following in the footsteps of Justin Timberlake, since he's just working from Jackson's playbook. (Allegedly, some of the Neptunes' beats for Justified were made for MJ.) Drake, on the other hand, has plenty of sons, and though Young Angel wouldn't have been able to break without the work of Kanye West and Kid Cudi, when I look at the contemporary pop landscape, it's not correct to describe the Drake clones as actually being Kanye (or Cudi) clones. What Drake and 40 created continues to impact the game on a massive level, even as Drake himself continues to absorb different sounds and styles (and accents). 

That said, I can see making the argument for Kanye, who is my ultimate 21st century star. Except that he's too mercurial and capricious for anyone to follow him well these days. The other weekend I listened to Yeezus three or four times, thinking about this tweet from the critic Ezra Marcus while I did so. Kanye works on a conceptual level in a way that's hard to crib from. But even that isn't enough to totally capture Kanye's singularity. Makes more sense to produce broken Auto-Tuned cries and wails for minutes at a time rather than use something as fragile as language to pin down Mr. West.

Taylor Weatherby: Okay fellas, I respect your opinions and respect the hell out of all of those artists, but y'all are taking this discussion way too seriously. Sure, novelty, influence and sentiment are all important to any artist, but when we’re thinking in terms of what defines a pop star, we’re talking worldwide relevance built on irresistible hits, performance skills (c’mon, we need a little of that choreo), an overall image -- and, perhaps most arguably against Drake and Kanye, true pop music. I realize that Drake and Kanye have been at the forefront of bringing hip-hop to the mainstream alongside other pop stars, but they’re rappers when it comes down to it. If we’re crowning the best pop star of the 21st century, let’s give it to someone who has the true pop roots: Justin Timberlake.

While there is a later generation still getting to know the singer behind “Can’t Stop the Feeling!,” '90s babies and older know that Timberlake has already been around for 20 years at this point. Starting out as the face of one of the most iconic pop groups of all time, *NSYNC, Timberlake established his destiny for superstardom — frosted tips and all — before his peers even graduated high school. He had the smooth and versatile voice, the looks, the suave dance moves, and the overall likability that you need to carry a career outside of a group setting. His transition to solo stardom was a bit abrupt for *NSYNC fans, but seamless in the grand scheme of things; and three Billboard 200 No. 1 albums, 18 Billboard Hot 100 top 10 hits and 15 years since his solo embark, here we are in 2018 anxiously awaiting the release of his fifth solo album and a Super Bowl halftime show performance.

As for the "student of Michael Jackson” component, it’s fair to call him a pupil and perhaps an emulation of what the King of Pop graced the music world with once upon a time. But by no means has Timberlake tried to -- or frankly, would he even be able to -- outshine Jackson’s legacy, and if we’re speaking in 21st century terms, Timberlake’s whole package of catchy hits and awe-inspiring dancing could very well crown him as the Prince of Pop (with Usher also being a close candidate for that title, arguably), especially considering their similar boy band beginnings. 

What’s more, Timberlake has established his relevance and appeal outside of the music realm, proving to be a force to be reckoned with on the acting front as well. You want to talk crossover appeal, let’s think about how many pop stars can say that they’re part of the prestigious Saturday Night Live Five-Timers Club (for the record, the answer is none). Look in the Mirrors and Cry Me A River, boys, because it’s hard to match the Sexyback what the iconic Justin Timberlake has brought — and will undoubtedly continue to bring, for years to come — to the pop world.

Denise Warner: I have to agree with Taylor here. If we're talking about a pure pop star, it's gonna be Justin Timberlake. 
Drake, Eminem, and Kanye perhaps have more influence on culture and music as a whole, but they don't dance. And I need my pop stars to dance.  Usher dances, but he when was the last time he had a hit? As for Justin Bieber, he is in a different category all together. If we were talking about who is the best "viral-prodigy-turned-legitimate-artist-who-is-still-more-tabloid-famous-than-music-famous" star, then it's Bieber hands down. But we're not. Bruno Mars comes close to Timberlake's cache -- but he hasn't been around long enough. (Although Mars' recent Grammy sweep means in a few years, we all might change our minds.)
 
JT is the complete package. He dances with MJ-esque skill. He produces infectious hits (yes, 20/20 parts I and II were very light on this brand of pop but after Justified and FutureSex/LoveSounds, he earned the right to experiment). He has grown musically from his *NSYNC days, but maintains the elemental star quality that made him the biggest breakout of that group and has established his own identity.

Plus, he turned a diehard Backstreet-girl into a big fan. What other evidence do you need?

Trevor Anderson: Three grab-bag thoughts before proceeding:

1. Kudos to Andrew for remembering Usher's sneakily consistent run from, really, 1997 through at least 2012. For some reason, it does feel shorter than it really was -- perhaps one of the downsides of having Confessions tower over his discography, but to have No. 1 hits courtesy of Jimmy Jam & Terry Lewis in your earlier days to will.i.am in your latter solidifies your standing.

2. Ross listened to Yeezus at least three times... this weekend alone? Impressive, with a side of madness.

3. Nice of Ross to use "absorb" to describe Drake's integration of new sounds - a word that navigates the tricky waters of what some would consider appropriation, even if I wouldn't (and even the most ardent critics still wind to his hits).

Back to Justin Timberlake -- I lean toward Taylor's defense of JT, but oddly enough, instead of her pop-centered defense, his ability to transcend the pure "pop star" label strengthens his claim to the throne for me. 

For an artist who, as Ross noted, was the star pupil of the Michael J. Jackson Academy for his solo debut (Justified), Timberlake banked left and spiced up his career by embracing hip-hop, R&B, and even elements of dance to a degree that surpasses what even the likeliest of the candidates listed above -- Usher, in my mind -- accomplished in that realm.

More importantly, he's gained the reciprocal respect from some of the century's big talents. When T.I., JAY-Z, Snoop Dogg, 50 Cent and Ciara needed a singer on their hook, Usher's phone didn't ring. When in 2008, Madonna was embarking on her fiftyleventh reinvention, Team Timberlake and Timberland were her saviors. (For comparison's sake -- Justin Timberlake has six top 10 Hot 100 hits in which he is a featured act, while Usher has only three in the top 25.) And yes, while some savvy chronological observers can note that T.I. and JAY-Z had recently collaborated with Justin at the time of his feature, I would emphasize again that they felt the same level of appreciation for his musicianship to return the favor and not pivot to any other option.

Plus, per Andrew's take on the wait between projects, let's not forget that Justin took a surprising six years and change between albums and didn't release anything of his own from 2008-2012. And yet, while most stars could never afford to enjoy such a hiatus without fading into irrelevance, we were all anxious when we saw that countdown on his website at the top of 2013 that heralded the third coming of Justin Timberlake -- "Could it be, he's back?" In the past decade, the only artist who's generated more buzz after such a dormant period is Adele.

Lastly, one more note on the "pop star" brand: He's evolved into much more than a Pop-Tart pop star. This is a guy who can show up at the Country Music Association (CMA) awards to perform alongside a non-pop-leaning artist in Chris Stapleton and produce the type of post-performance fervor that every Grammys mashups wishes to inspire. But then, this same white guy can roll up to the Black Entertainment Television's annual awards show to pay tribute to Charlie Wilson, and no one asks, "What is he doing here?" 

Drop Timberlake in any era and he'll rise to the top - including this one.

Super Bowl 52