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

With the primary quarter of the twenty first century coming to an in depth, Billboard is spending the subsequent few months counting down our workers 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 and No. 22 stars, and now we bear in mind the century in Lil Wayne — who turned common music into Wayne’s World for a lot of the late ’00s, and helped elevate an empire that will rule pop and hip-hop for all the 2010s.

Even 25 years after notching his first Billboard Sizzling 100 entry, Lil Wayne stays a fixture within the rap scene, and unquestionable as one of the influential hip-hop artists of all-time. Take a snapshot of rap when Wayne entered the sport after which survey as we speak’s panorama and it’s straightforward to see: Simply take a look at all of the “Lil’s” working round, rappers with grills and face tattoos whereas sporting dreadlocks and all of it might be traced again to the New Orleans rap deity – even when the neophyte MCs can’t mimic his AutoTune-drenched rhymes and genius punchlines. Or let Wayne himself inform it: “Earlier than I stepped into music, everybody regarded a sure manner and everybody did a sure factor. Have a look at me. Now take a look at music. All of them appear like me,” he mentioned in 2020. “I find it irresistible.”

As soon as Wayne invaded the “Finest Rapper Alive” dialogue within the mid-’00s, he started cementing his standing as a industrial titan even past hip-hop. Everybody from Enrique Iglesias to Shakira needed a bit of Weezy, whose grill-bearing smile turned unavoidable in popular culture and led to him defining an period of hip-hop throughout a time the place rap basically turned interchangeable with pop, on its technique to rising as music’s most-consumed style. Oh, and he launched the world to Drake and Nicki Minaj below his Younger Cash imprint, who would go on to be much more dominant than him inside pop music within the decade to comply with. 

Lengthy earlier than his mixtape supremacy, lighter flicks and Bape camouflage, Weezy received his ft moist establishing himself as a prodigy within the Money Cash Information military and the youngest member of the Sizzling Boys. Wayne completed the twentieth century on a excessive observe — and proved able to take over for the 2000s as only a 16-year-old — with appearances on a pair of lexicon-expanding classics, when he had the nation hollering “Bling Bling” on B.G.’s diamond-inspired hit, and dropped it prefer it’s sizzling on Juvenile’s “Again That Azz Up” anthem.

It was Lil Wayne’s flip to step into the solo highlight together with his uncooked Tha Block Is Sizzling debut in late ‘99, which peaked at No. 3 on the Billboard 200 and spawned a Sizzling 100 hit with the title monitor, assisted by the aforementioned Sizzling Boys, B.G. and Juvenile. After his subsequent two albums delivered middling industrial efficiency, Lil Wayne went again to the drafting board – and threw his notepad within the trash after studying Jay-Z was freestyling, which led to the beginning of the collection that outlined Weezy’s profession.

It was really Money Cash sonic savant Mannie Recent who possessed the foresight to foretell that Tha Carter collection would go on to reside in rap lore as one of many paramount collection within the style’s historical past. “I’m like, ‘Tha Carter goes to outline rap for some time.’ Wayne was like, ‘You actually assume?’ I’m like, ‘I actually do. It’s received to be one thing unbelievable,” Mannie Recent recalled to Advanced.

MF broke out the Roland TR-808 drum machine and received Weezy excessive on his provide. Impressed by ‘90s Money Cash Information group U.N.L.V.’s shout-out to the in-house producer, Wayne carried the baton with “Go DJ.” The spacey monitor cracked the Sizzling 100’s high 15, proving he might carry a serious hit on his personal. The pop world additionally started to take discover of Weezy’s taking pictures stardom, as Future’s Little one enlisted Lil Wayne and then-consensus King of the South T.I. to mobilize for high 5 Sizzling 100 hit “Soldier,” which was nominated for greatest rap/sung collaboration on the 2005 Grammys.

He stored constructing momentum into Tha Carter II, which arrived in late 2005. Wayne definitely by no means lacked confidence, however C2 noticed him crowning himself the “Finest Rapper Alive” with a tune named simply that – and following the album’s launch, the remainder of the world was beginning to consider it, too. Weezy had refined his rapping model and prolonged his manufacturing limitations outdoors of the Mannie Recent and Money Cash Information nest, which led to an album that many take into account the crown jewel of his discography. The set netted Wayne one other high 40 Sizzling 100 hit with “Fireman,” however the one flame that couldn’t be contained within the coming years was his personal.  

There wasn’t a minute to be wasted within the time between Tha Carter II to C3, with Wayne climbing larger into rap’s pantheon. Weezy turned a machine, churning out cheeky punchlines and Auto-Tune-laced rhymes and seemingly by no means working out of gasoline. He painted vivid photos of heartbreaking love tales and dirty avenue tales like a chameleon, disappearing into his songs’ canvases.

Throughout this time, he proved himself within the mixtape circuit – unleashing fan-favorite classics just like the DJ Drama-hosted Dedication 2 and Da Drought 3, which fortified his legend among the many underground hip-hop heads. The cultural influence of Wayne’s mixtapes run is actually incalculable, for the reason that Billboard charts didn’t account for DatPiff downloads and circulating Limewire information, however most of the tracks reside on in iTunes libraries and the hearts of followers as holy grails of that Weezy interval. 

In the meantime, if an artist wanted a visitor verse within the second half of the ‘00s, there was just one rapper to name. Wayne sprinkled his syrupy flows onto myriad high 40 Sizzling 100 hits from ‘06 to C3’s arrival in June ‘08, like Chris Brown’s “Gimme That,” Lloyd’s “You,” Fats Joe’s “Make It Rain,” DJ Khaled’s “We Takin Over,” Wyclef Jean’s “Sweetest Lady,” Playaz Circle’s “Duffle Bag Boy,” Birdman’s “Pop Bottles” and Usher’s “Love in This Membership Half II.” Within the midst of his run, Weezy additionally teamed up together with his mentor Birdman for his or her Like Father, Like Son joint venture, as he turned completely unavoidable each on radio and on video networks MTV and BET. 

Even with Wayne’s vociferous output, there was nonetheless ample urge for food for extra music. It received to the purpose that songs have been being leaked on-line, which pressured Weezy to proceed reshaping his imaginative and prescient for Tha Carter III. He even quick-released a five-track EP of songs that had already circulated on the web, with 2007’s aptly titled The Leak.  

Coming off his “I’ve arrived” second with the debut efficiency of “Gossip” on the ‘07 BET Hip-Hop Awards, expectations couldn’t have been larger for C3 – and Wayne nonetheless calmly pole vaulted over the clouds to etch his identify into the hip-hop historical past books. Tha Carter III arrived on June 10, 2008, because the soundtrack to the summer season, whereas debuting atop the Billboard 200 with over a million data offered within the first week – his first No. 1 LP. It’s the final hip-hop album to hit the seven-digit gross sales mark in a weekly interval, outdoors of Drake’s Views in 2016. 

The album, which might additionally go on to win the Grammy for greatest rap album, was Wayne’s sonically richest but, resisting any straightforward regional pigeonholing, as Wayne served up one thing for everybody. The bold C3 produced three main Sizzling 100 hits, because the extraterrestrial double-entendre of “Lollipop” that includes the late Static Main topped the Sizzling 100 for 5 nonconsecutive weeks, whereas the T-Ache-assisted strip membership anthem “Received Cash” and the blazing-though-hookless “A Milli” additionally cracked the highest 10. (Who might overlook Wayne’s day within the life on set for the “A Milli” visible?) Even the duvet artwork, that includes Wayne as a child with face tattoos, has lived on as iconic. 

Tha Carter III encapsulated every little thing Wayne needed to supply from his versatile repertoire. Whether or not he was barring up towards Jay-Z on “Mr. Carter” or enjoying rapper-doctor on “Dr. Carter,” he jumped round with ease. Weezy even supplied social commentary on political matters like President Bush’s inaction when it got here to Hurricane Katrina aid in his hometown (on “Tie My Arms”) or condemning the felony justice system and Reverend Al Sharpton (on “Don’t Get It”). Lil Uzi Vert would later say of Weezy: “After I heard Tha Carter III, I knew Wayne was the best rapper alive.”

It’s powerful to consider when you didn’t reside by way of it, however Lil Wayne had presumably the best peak of any rapper ever circa Tha Carter III. Whereas rap titans Kanye West, Jay-Z and Eminem have been dominating, Weezy had maybe the very best degree of respect and basic approval ranking of his friends, followers and critics at that time. Ye himself known as Wayne his “fiercest competitors” whereas on stage on the ‘08 BET Awards. “You scare me, man, each time you spit,” West mentioned.  

This was Wayne’s MVP Award and championship run, like 2012 LeBron James or ‘92 Michael Jordan. The New Orleans dignitary was a participant that was robotically on hearth anytime he stepped into the sales space. Severely, every little thing he touched seemingly turned to gold. Established because the millennials’ rap superhero, Lil Wayne led from the highest of the meals chain – even when clashing together with his celebrity friends on supercharged posse cuts like “Swagga Like Us” (No. 5 Sizzling 100).

With Weezy on the peak of his powers, he was basically minting new hitmakers on radio seemingly on a weekly foundation, spamming the airwaves with appearances on smashes by artists like Kevin Rudolf (“I Made It,” “Let It Rock”) and Jay Sean (“Down”). The latter topped the Sizzling 100, and Wayne’s memorable verse – and ideas on the financial system – stay a staple in rotation for DJ units at bars throughout the nation. All artists needed a bit of Lil Wayne at this level, as his Wayfarer sun shades, tattoos and purple Bape jacket turned imagery ingrained in American popular culture. 

On the high of the sport, Wayne examined the depths of his artistry together with his newfound guitar abilities when he zagged into the rock-leaning Rebirth. He was most likely a couple of years too early on the rock star wave that got here to the hip-hop mainstream with the subsequent era of rhymers like XXXTENTACION, Lil Uzi Vert, Trippie Redd and Playboi Carti. Nonetheless, the album debuted at No. 2 on the Billboard 200, whereas Weezy’s six-string classes on the pummeling shout-along “Promenade Queen” nonetheless made it to the Sizzling 100’s high 15.

Within the midst of the industrial peak of his profession, Lil Wayne was additionally fascinated by the subsequent era of rappers. By the top of the 2000s, he’d signal two artists who would take what he’d constructed with Younger Cash to the subsequent degree within the following decade — Drake and Nicki Minaj — in addition to fellow up-and-comers like Tyga and Jae Millz. The We Are Younger Cash compilation album arrived in Dec. 2009 to help in spotlighting among the proficient artists working behind Wayne. The venture ended up spawning hits just like the raunchy polyamorous posse lower “Each Lady” and the Lloyd-assisted crowd-pleaser “Bedrock,” which hit No. 2 and offered early memorable solo moments for each Drake and Nicki.

An eight-month jail stint on Rikers Island in NYC for a gun cost pressured the always-moving Lil Wayne to sit down down for a lot of 2010, as he pressed pause for the primary time in a very long time and briefly took off the “Finest Rapper Alive” crown. Nonetheless, the motivational horns of “Proper Above It” with Drake managed to invade the Sizzling 100’s high 10 from behind bars, following a premiere from Sizzling 97’s Funkmaster Flex. Highschool soccer gamers throughout the U.S. made the Kane Beatz-produced beat the soundtrack to their spotlight tapes whereas the ladies strolling the hallways up to date their Fb statuses in unison to Wayne’s feel-good, “Life’s a seashore, I’m simply enjoying within the sand” bar. 

It didn’t take lengthy for Wayne to get again on monitor following his launch from Rikers. Tha Carter IV’s lead single “6 Foot 7 Foot” – which felt just like the cousin to C3’s “A Milli” – gave him one other high 10 entry on the Sizzling 100, and earned his seat again on the rap council. Teaming up with good friend DJ Khaled has lengthy been a fruitful components for Wayne, and so they additionally scored one other hit heading into the summer season of 2011 with “I’m on One” alongside Drake and Rick Ross. In the meantime, a pair of C4 advance singles – the smoky, bar-heavy “She Will” and the acoustic ballad “ Love” – showcased the duality of Wayne’s artistry, and each reached the Sizzling 100’s high 5. 

After a number of delays, Tha Carter IV lastly arrived to shut out the summer season on Aug. 28, 2011, and the fourth installment within the adorned collection simply missed out on being Wayne’s second launch to succeed in the million mark – transferring 964,000 complete album items in its first week whereas debuting at No. 1. Whereas the venture wasn’t as acclaimed or beloved as C3, it confirmed that even Wayne’s B-game might nonetheless surpass most hitmakers on their greatest day. 

A lot of the 2010s resulted in inventive frustration for Lil Wayne, who was entrenched in a nasty $51 million lawsuit together with his mentor Birdman and Money Cash Information over monetary compensation. The 2 events would find yourself settling in June 2018 after three years of litigation, which lastly cleared the way in which for the much-delayed Tha Carter V. However even throughout that in-between interval, Wayne was nonetheless lively, making methods on the characteristic entrance by reuniting with Chris Brown on “Loyal” – which reached the highest 10 and spent 9 months on the Sizzling 100 in 2014 – and incomes help wins on DJ Khaled’s No. 1 hit “I’m the One,” French Montana’s “Pop That” and Likelihood The Rapper’s “No Drawback,” and scoring one other high 10 hit of his personal with the Drake- and Future-assisted “Love Me.”

On the identical time, Wayne poured time and vitality into constructing his proteges Drake and Nicki into stars in their very own proper, as he popped up on their albums for visitor verses and remixes at any time when wanted. Whereas Drizzy and Minaj took the baton and in the end surpassed Weezy’s pop stardom in their very own wildly profitable crossover careers, they nonetheless all the time pay homage to Wayne because the GOAT, and proceed shouting him out for giving them an opportunity and serving to them obtain their rap goals.

As Wayne’s sizzling streak started to chill down within the mid-2010s, so did his industrial visibility. Nevertheless, one other chapter of Tha Carter was nonetheless sufficient to push the rap world’s hype into overdrive as soon as once more.

The seven-year build-up main into C5 was going to be practically inconceivable for Wayne to match, because the venture hit streaming companies on his thirty sixth birthday in 2018. Although the LP didn’t reside as much as the standard of earlier installments, Tha Carter V was nonetheless a serious industrial success – debuting at No. 1 with 480,000 items moved and netting Wayne the second-most first-week streams ever (behind Drake’s Scorpion), whereas additionally making him the primary artist to launch a pair of debuts within the Sizzling 100’s high 5 (“Mona Lisa” that includes Kendrick Lamar and “Don’t Cry” with XXXTENTACION). 

Funeral scored Weezy one other No. 1 album to start out the 2020s off on the precise foot, however not one of the tracks caught on the charts, as his days as a number one hitmaker gave the impression to be behind him.  Nonetheless, in an period the place remixes really feel formulaic and hole, Wayne shined brilliant on Jack Harlow’s “WHATS POPPIN (Remix)” with Tory Lanez and DaBaby, as Weezy’s co-sign on the fiery remix helped elevate Harlow to mainstream stardom and spent 51 weeks on the Sizzling 100 (whereas peaking at No. 2) in the course of the COVID-19 pandemic. As of late, Lil Wayne’s telephone continues to be buzzing as one of the in-demand characteristic artists in all of hip-hop – together with for the subsequent era, with youthful rap stars like Polo G, Cordae, Trippie Redd, YoungBoy By no means Broke Once more and J.I.D. tapping Wayne for verses this decade – however as an alternative of his Sidekick, it’s simply an iPhone.

Three many years for the reason that self-inflicted gunshot wound at house that just about took his life, Wayne has scored 186 Sizzling 100 hits – fifth most of any artist in chart historical past – and gained 5 Grammys. Weezy’s timelessness and wordplay wizardry has him serving up razor-sharp verses with eccentricities which can be typically imitated however might by no means actually be duplicated. Perhaps he actually was an alien all alongside. 

Learn extra in regards to the Best Pop Stars of the twenty first Century right here and test again on Friday when our No. 20 artist is revealed!