Best Pop Singers of 21st Century (No. 18)

With the primary quarter of the twenty first century coming to a detailed, Billboard is spending the following few months counting down our employees picks for the 25 best pop stars of the final 25 years. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20 and No. 19 stars, and now we bear in mind the century in The Weeknd — who emerged within the shadows as an early-’10s mixtape sensation, earlier than making a extra profitable pivot to pop stardom than anybody might have guessed.

A couple of dozen years in the past, no one would’ve believed the hedonistic, alt-R&B, then-cult determine generally known as The Weeknd would turn into one of many twenty first century’s most adorned and sturdy pop artists, dominating each the Billboard charts and the world’s greatest stadiums. International superstardom won’t have appeared instantly on the horizon upon his 2011 mixtape arrival, however his capability to carve his personal path in R&B earlier than efficiently switching lanes to pop has made his journey one of the crucial fascinating ones to observe this century.  

Born Abel Tesfaye to Ethiopian immigrant dad and mom within the Toronto suburb of Scarborough, The Weeknd dropped out of highschool at 17 along with his greatest buddy and now inventive director La Mar Taylor and moved out of his household’s dwelling one weekend (wink wink). Homelessness, substance abuse and run-ins with the regulation compelled him to get his act collectively, so he translated the ill-advised way of life of his youth to his music.  

In 2010, The Weeknd anonymously uploaded three moody, atmospheric R&B tracks – “What You Want,” “Loft Music” and “The Morning” – onto his YouTube. Fellow Torontonian (after which rap’s brightest budding star) Drake observed the songs and featured them on his OVO Weblog – a key co-sign that projected The Weeknd’s title (and nonetheless not his face) within the media earlier than he dropped his debut mixtape Home of Balloons without cost on his web site in March 2011. The songs stretched for 5, six, even seven minutes, with The Weeknd’s wailing falsetto and supple tenor from the Michael Jackson vocal academy reliving his pill-popping and bed-hopping escapades and different foggy morning-after recollections, via the attitude of somebody who’s perpetually trying to interchange his ache with pleasure in a numbing rinse-and-repeat cycle.  

In the meantime, his sampling of indie and post-punk rock bands like Siouxsie & the Banshees, Cocteau Twins and Seaside Home, together with different hip-hop and digital influences, eternally shifted the R&B panorama — and helped usher the style’s various shift, alongside different enigmatic artists like Frank Ocean. And when it was lastly time to disclose himself at his now-iconic debut live performance at Toronto’s 600-capacity Mod Membership in July 2011, it was the must-see present of the town: The promotional flyer indicated there was “no guestlist,” however that didn’t cease main U.S. label executives from catching last-minute flights up north to see what the hell The Weeknd was even about and if he lived as much as the web hype. (A former MuchMusic worker tells me she remembers one even providing her $1300 CAD for her ticket that she purchased for $20.)  

Later that very same yr, he launched two extra mixtapes –Thursday and Echoes of Silence – that invited us to enterprise deeper into The Weeknd’s world of debauchery and self-destruction. Together with his cult-classic trilogy, The Weeknd firmly established himself as lord of the R&B underworld. Within the four-month interval between the latter two tapes, he was additionally throughout Drake’s emo magnum opus Take Care, co-writing 5 songs and being featured on the chant-along banger “Crew Love.” The kinship between the 2 Canadian phenoms generated a whole lot of hypothesis that Drake would signal The Weeknd to OVO, however he continued carving out his personal lane, and based his XO label (followers have debated on Reddit threads whether or not it stands for “hugs and kisses” or “ecstasy and oxycontin”), signing to Republic Information the next yr. Given The Weeknd’s “I thank God that I by no means signed my life away” line from Future and Metro Boomin’s “All to Myself” throughout 2024’s Nice Rap Beef™, it’s protected to say he believes he made the suitable resolution there.  

Tesfaye had steadily constructed up momentum for his main label debut studio album Kiss Land in 2013, however takeoff there was a bit turbulent. It appeared like he had exhausted his nihilistic, narcotic-fueled aesthetic – and having already consumed what felt like three albums in underneath one calendar yr, we had been form of exhausted, too. Possibly why Kiss Land fell a bit flat was as a result of the aura behind The Weeknd was additionally fading, particularly along with his face and Jean-Michel Basquiat-esque dreads entrance and heart on the album cowl. Regardless that Kiss Land entered the Billboard 200 at No. 2, it wasn’t the optimum introduction for an artist who had been cranked out of the web hype machine – and it acquired combined evaluations, whereas failing to supply successful single. 

However the false begin didn’t cease Tesfaye from constructing a much bigger breakout second. Ariana Grande, the Nickelodeon-bred pop princess who signed to Republic the yr earlier than The Weeknd, recruited him for her My The whole lot single “Love Me More durable.” The lip-biting ruminations about tough intercourse gave Grande extra edge, whereas the tune’s throbbing synthwave-R&B manufacturing – courtesy of twenty first century-defining producer Max Martin (who would go on to play an important function in Tesfaye’s profession) – softened The Weeknd’s. It’s the primary tune to affirm his mainstream ambitions, as Tesfaye earned his first Billboard Scorching 100 high 10 hit. Grande would go on to turn into one in all his most dependable hit collaborators a decade later, hopping on the remixes of “Save Your Tears” from his 2020 album After Hours, which they carried out collectively on the 2021 iHeartRadio Music Awards, and “Die For You” – which skilled a TikTok resurgence six-plus years after it first appeared on his Starboy album – each of whichwould then shoot to No. 1.  

4 months after “Love Me More durable,” Tesfaye was tapped to file “Earned It” from the Fifty Shades of Gray soundtrack. Essentially the most sexually express R&B singer of the time singing for the yr’s most titilating mainstream movie? It felt so flawed, however oooh was it so proper. The orchestral pop ballad launched The Weeknd’s slow-burning seductive vocals to a a lot wider viewers. “Earned It” turned The Weeknd’s first solo Scorching 100 high 10 hit (No. 3), gained a Grammy Award for greatest R&B efficiency and scored an Oscar nomination for greatest authentic tune.  

The Weeknd’s mid-2010s pop pivot was nicely underway, however now he wished to show he might pull it off with out the help of an A-list artist or buzzy film franchise with “Can’t Really feel My Face.” The licensed smash earned him extra MJ comparisons than when Tesfaye put his skeletal cowl of “Soiled Diana” on Echoes of Silence, particularly his screeching ad-libs that felt plucked straight from Jackson’s “Don’t Cease ‘Til You Get Sufficient” and his slick footwork and signature spin within the music video. Together with his reliable hitmaking staff from “Love Me More durable” – Max Martin, Savan Kotecha, Ali Payami and Peter Svensson – Tesfaye had efficiently damaged although pop’s ceiling after initially cracking it with “Love Me More durable” and “Earned It.” “Face” finally turned The Weeknd’s first Scorching 100 chart-topper, and a runaway radio smash that had us simply as hooked as Tesfaye was on blow (or so he semi-subtly sang). It additionally earned a favourite tune of the yr nomination on the 2016 Nickelodeon Children’ Alternative Awards, which he hilariously referenced within the Starboy lower “Reminder”: “I simply gained a brand new award for a youngsters present/ Talkin’ ‘bout a face numbin’ off a bag of blow.” The Weeknd’s lyrical knack for disguising his NSFW fixations in PG-rated, radio-friendly hooks would give him a intelligent edge. 

Surprisingly, follow-up “The Hills” could be even larger. Horrifying shrieks, sparse entice beats and Tesfaye’s hoarse verses about life within the quick lane felt like a return to type to his mixtapes’ murkier R&B – with its outro sung in his native Amharic, the first language of Ethiopia, to additional floor himself in his roots – and with out compromising “the true me,” it turned the basic crossover smash of his profession. The Weeknd changed himself at No. 1 on the Scorching 100, with “The Hills” dethroning “Can’t Really feel My Face” after its three-week non-consecutive run and remaining on high for six straight weeks.  

His chart reign gave him the boldness to make his mainstream bid with Magnificence Behind the Insanity. The album, which accomplished his transition from respected R&B singer-songwriter to perennial pop star, was marked by much more irresistible MJ-inspired bangers (“In The Evening”) and lovelorn, instrumental-driven ballads (“Angel” and “Shameless”). On the Ye-produced, soul-sampling “Inform Your Associates,” The Weeknd sums up simply precisely who he’s: “I’m that n—a with the hair/ Singin’ ‘bout popping’ drugs, f—kin’ b—-es, livin’ life so trill.” Magnificence turned The Weeknd’s first No. 1 album on the Billboard 200 and planted him firmly within the highlight he had shied away from only a few quick years in the past.   

And as he began sounding extra like a pop star, he additionally began trying like one, too, with a headline-making haircut. He kills his former self and smashes his accolades to the beat of the title observe’s snare within the music video for his third Scorching 100 No. 1 “Starboy,” that includes Daft Punk. Starboy turned his second Billboard 200-topping album and earned him his second greatest city up to date album Grammy win, proving that lightning can strike twice.  

His high-profile relationships with mannequin Bella Hadid and fellow singer Selena Gomez impressed his 2018 EP My Expensive Melancholy,. Revealing he volunteered to donate his kidney to Gomez (who acquired a transplant in 2017 amid her battle with lupus) on the desolate opener “Name Out My Title” set the tone for the heart-wrenching six-song set, which represented a sobering sonic departure from the resplendent pop of Magnificence Behind the Insanity and Starboy. However the vulnerability – which was on full show at his first Coachella headlining gig the next month – recaptured the darkish magic of his early mixtapes. And it was a successful formulation: My Expensive Melancholy, earned Tesfaye his third consecutive Billboard 200 No. 1. 

The album rollout for 2020’s After Hours period unfolded like a masterclass in world-building, with The Weeknd enjoying a pink swimsuit jacket-, black leather-based glove-, black sunglasses-wearing character, his face additional hid by bloodied facial bandages, that will convey mischief and mayhem to music movies and late-night TV and award present performances. We might first meet him within the visible for “Heartless,” a hedonistic trap-tinged R&B file the place The Weeknd boasts within the first line, “By no means want a b—h, I’m what a b—h want” and licks a psychedelic-laced frog.  

The tune turned The Weeknd’s fourth No. 1, however it will be the LP’s second single that will alter pop music historical past. As Billboard’s high Scorching 100 tune of all time, “Blinding Lights” is an adrenaline-pumping, synth-pop juggernaut that beamed brighter than the marquee lights of its Las Vegas Strip backdrop and entered the cultural zeitgeist. Solely The Weeknd might flip a tune about drunk driving to a hookup (that premiered in a Mercedes Benz industrial, no much less) into the longest-running Radio Songs No. 1 (26 weeks) and the most-streamed tune on Spotify whereas additionally soundtracking over one million TikTok dance movies that includes frontline healthcare staff and quarantined households alike.  

With its dad or mum album After Hours, he nailed one in all pop music’s tenets – making private themes common – and with the pandemic, The Weeknd’s motifs of loneliness and escapism felt much more relatable. That’s why After Hours and Dua Lipa’s ‘70s disco-inspired album Future Nostalgia (launched one yr later in March 2020) got here on the proper time, as a result of they cranked up the BPMs of high 40 and helped usher in pop’s retro dance-driven renaissance (years earlier than Beyoncé’s Renaissance) throughout one of many world’s darkest years in latest historical past.  

After Hours debuted atop the Billboard 200, however when it and “Blinding Lights” shockingly acquired zero nominations on the 2021 Grammys, critics and his friends like Drake and Child Cudi sneered on the snub. “The Grammys stay corrupt,” The Weeknd retaliated on X (previously generally known as Twitter), including in a press release to The New York Occasions that he “will now not enable my label to submit my music to the Grammys.” (He nonetheless took dwelling a statue in 2022 for his characteristic on Ye’s “Hurricane” with Lil Child.) Whereas The Weeknd was lacking from Music’s Largest Evening, he was entrance and heart on the world’s greatest stage a month earlier: the Tremendous Bowl LV Halftime Present. And the penultimate efficiency of his Home of Balloons title observe, backed by a marching military of bandaged lookalikes, that finally revved as much as the exhilarating pace of “Blinding Lights,” made for a real career-spanning victory lap second.  

As he continued using the highs of his blockbuster After Hours period, followers puzzled the place The Weeknd might presumably go subsequent. On his extremely anticipated follow-up, Daybreak FM, he confirmed us precisely the place he was taking us: With the assistance of Jim Carrey, who was posing as purgatory’s radio DJ, we had been headed towards the sunshine on the finish of the tunnel. The Weeknd soundtracked the ominous journey by zeroing in on After Hours’ synth-pop infatuation to create levity on tracks just like the spellbinding dancefloor quantity “Take My Breath,” which peaked at No. 6 on the Scorching 100, and “Sacrifice,” the place Tesfaye will get as shut as he ever has to sounding just like the King of Pop. However not like its blockbuster predecessor, Daybreak FM failed to supply a surefire hit. Daybreak FM entered the Billboard 200 at No. 2, a slight misstep for somebody who had notched 4 consecutive No. 1 albums, however an inconsequential one for somebody who had already been topped pop royalty. 

The Weeknd didn’t put out any new solo studio releases in 2023, however his standing as a no-doubt celebrity allowed him to relaxation on his laurels and benefit from the fruits of his labor. With the Grande-assisted “Die for You” going No. 1, The Weeknd joined Michael Jackson as the one male soloists with a number of leaders on the chart from three completely different albums. Not unhealthy for a man who’s spent his whole profession emulating the King of Pop. Guinness World Information additionally named him the world’s hottest artist after he turned the primary artist to achieve 100 million month-to-month listeners on Spotify. He was Spotify’s most streamed month-to-month artist for over a yr, till Billie Eilish not too long ago took the title – and his untimely supportive response steered a heavyweight like him wasn’t threatened by another person holding the championship belt. The Weeknd additionally headlined Coachella once more alongside Swedish Home Mafia, getting into an elite group of acts who’ve headlined the pageant twice (and being the primary non-alternative/rock act to take action). His set served as a warm-up for his After Hours Til Daybreak Tour, with its first leg and second leg incomes spots on 2022 and 2023’s high 10 grossing excursions record. 

And for a break up second, his stadium stint doubled because the set for his HBO sequence The Idol, which follows troubled pop star Jocelyn (performed by Lily-Rose Depp) who develops an advanced relationship with Tesfaye’s character Tedros, a sleazy nightclub proprietor/cult chief who yearns to pilot her profession comeback. Regardless of critics and viewers largely rebuking the controversial sequence, which acquired a 19% rating on Rotten Tomatoes and was swiftly canceled after 5 episodes, The Idol managed to win an Emmy (excellent choreography for scripted programming) ultimately weekend’s Inventive Arts Emmys and win again some credibility with its soundtrack. The Weeknd fashioned an uncommon, but efficient alliance with the Queen of Pop Madonna and the King Vamp Playboi Carti on the platinum-certified “Standard” that harkened again to the slinky 2000s pop&B that The Neptunes dominated, and entered right into a musical threesome with BLACKPINK’s Jennie and Depp on the erotic, down-tempo “One of many Women,” which reached No. 10 on the Billboard International 200.  

Earlier this September, he introduced the third and closing installment of his After Hours/Daybreak FM trilogy, Hurry Up Tomorrow, a bittersweet means of sunsetting this chapter of his profession: He advised W Journal final yr that this album “might be my final hurrah as The Weeknd.” Its lead single, “Dancing within the Flames,” is out Friday (Sept. 13), and the shimmering snippet suggests he’s delivering one more slice of retro-pop brilliance. However even when The Weeknd as we’ve come to know and love him ceases to exist, his transition from subterranean R&B auteur to ubiquitous genre-bending celebrity – and the numerous alt-R&B neophytes and would-be eletro-pop stars he’s fathered within the years between – he’ll eternally go down as one of the crucial outstanding artists, with one of the crucial outstanding profession arcs, in fashionable pop music historical past.  

Learn extra concerning the Biggest Pop Stars of the twenty first Century right here — and make sure to examine again on Tuesday when our No. 17 artist is revealed!