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

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23 and No. 22 stars, and now we remember the century in Lil Wayne — who turned popular music into Wayne’s World for much of the late ’00s, and helped raise an empire that would rule pop and hip-hop for the entire 2010s.

Even 25 years after notching his first Billboard Hot 100 entry, Lil Wayne remains a fixture in the rap scene, and unquestionable as one of the most influential hip-hop artists of all-time. Take a snapshot of rap when Wayne entered the game and then survey today’s landscape and it’s easy to see: Just look at all the “Lil’s” running around, rappers with grills and face tattoos while sporting dreadlocks and it all can be traced back to the New Orleans rap deity – even if the neophyte MCs can’t mimic his AutoTune-drenched rhymes and genius punchlines. Or let Wayne himself tell it: “Before I stepped into music, everyone looked a certain way and everyone did a certain thing. Look at me. Now look at music. They all look like me,” he said in 2020. “I love it.”

Once Wayne invaded the “Best Rapper Alive” discussion in the mid-’00s, he began cementing his status as a commercial titan even beyond hip-hop. Everyone from Enrique Iglesias to Shakira wanted a piece of Weezy, whose grill-bearing smile became unavoidable in pop culture and led to him defining an era of hip-hop during a time where rap essentially became interchangeable with pop, on its way to emerging as music’s most-consumed genre. Oh, and he introduced the world to Drake and Nicki Minaj under his Young Money imprint, who would go on to be even more dominant than him within pop music in the decade to follow. 

Long before his mixtape supremacy, lighter flicks and Bape camouflage, Weezy got his feet wet establishing himself as a prodigy in the Cash Money Records army and the youngest member of the Hot Boys. Wayne finished the 20th century on a high note — and proved ready to take over for the 2000s as just a 16-year-old — with appearances on a pair of lexicon-expanding classics, when he had the country hollering “Bling Bling” on B.G.’s diamond-inspired hit, and dropped it like it’s hot on Juvenile’s “Back That Azz Up” anthem.

It was Lil Wayne’s turn to step into the solo spotlight with his raw Tha Block Is Hot debut in late ‘99, which peaked at No. 3 on the Billboard 200 and spawned a Hot 100 hit with the title track, assisted by the aforementioned Hot Boys, B.G. and Juvenile. After his next two albums delivered middling commercial performance, Lil Wayne went back to the drawing board – and threw his notepad in the trash after learning Jay-Z was freestyling, which led to the birth of the series that defined Weezy’s career.

It was actually Cash Money sonic savant Mannie Fresh who possessed the foresight to predict that Tha Carter series would go on to live in rap lore as one of the paramount series in the genre’s history. “I’m like, ‘Tha Carter is going to define rap for a while.’ Wayne was like, ‘You really think?’ I’m like, ‘I really do. It’s got to be something incredible,” Mannie Fresh recalled to Complex.

MF broke out the Roland TR-808 drum machine and got Weezy high on his supply. Inspired by ‘90s Cash Money Records group U.N.L.V.’s shout-out to the in-house producer, Wayne carried the baton with “Go DJ.” The spacey track cracked the Hot 100’s top 15, proving he could carry a major hit on his own. The pop world also began to take notice of Weezy’s shooting stardom, as Destiny’s Child enlisted Lil Wayne and then-consensus King of the South T.I. to mobilize for top five Hot 100 hit “Soldier,” which was nominated for best rap/sung collaboration at the 2005 Grammys.

He kept building momentum into Tha Carter II, which arrived in late 2005. Wayne certainly never lacked confidence, but C2 saw him crowning himself the “Best Rapper Alive” with a song named just that – and following the album’s release, the rest of the world was starting to believe it, too. Weezy had refined his rapping style and extended his production barriers outside of the Mannie Fresh and Cash Money Records nest, which led to an album that many consider the crown jewel of his discography. The set netted Wayne another top 40 Hot 100 hit with “Fireman,” but the only flame that couldn’t be contained in the coming years was his own.  

There wasn’t a minute to be wasted in the time between Tha Carter II to C3, with Wayne climbing higher into rap’s pantheon. Weezy became a machine, churning out cheeky punchlines and Auto-Tune-laced rhymes and seemingly never running out of fuel. He painted vivid pictures of heartbreaking love stories and grimy street tales like a chameleon, disappearing into his songs’ canvases.

During this time, he proved himself in the mixtape circuit – unleashing fan-favorite classics like the DJ Drama-hosted Dedication 2 and Da Drought 3, which fortified his legend among the underground hip-hop heads. The cultural impact of Wayne’s mixtapes run is essentially incalculable, since the Billboard charts didn’t account for DatPiff downloads and circulating Limewire files, but many of the tracks live on in iTunes libraries and the hearts of fans as holy grails of that Weezy period. 

Meanwhile, if an artist needed a guest verse in the second half of the ‘00s, there was only one rapper to call. Wayne sprinkled his syrupy flows onto myriad top 40 Hot 100 hits from ‘06 to C3’s arrival in June ‘08, like Chris Brown’s “Gimme That,” Lloyd’s “You,” Fat Joe’s “Make It Rain,” DJ Khaled’s “We Takin Over,” Wyclef Jean’s “Sweetest Girl,” Playaz Circle’s “Duffle Bag Boy,” Birdman’s “Pop Bottles” and Usher’s “Love in This Club Part II.” In the midst of his run, Weezy also teamed up with his mentor Birdman for their Like Father, Like Son joint project, as he became totally unavoidable both on radio and on video networks MTV and BET. 

Even with Wayne’s vociferous output, there was still ample appetite for more music. It got to the point that songs were being leaked online, which forced Weezy to continue reshaping his vision for Tha Carter III. He even quick-released a five-track EP of songs that had already circulated on the internet, with 2007’s aptly titled The Leak.  

Coming off his “I’ve arrived” moment with the debut performance of “Gossip” at the ‘07 BET Hip-Hop Awards, expectations couldn’t have been higher for C3 – and Wayne nonetheless calmly pole vaulted over the clouds to etch his name into the hip-hop history books. Tha Carter III arrived on June 10, 2008, as the soundtrack to the summer, while debuting atop the Billboard 200 with over one million records sold in the first week – his first No. 1 LP. It’s the last hip-hop album to hit the seven-digit sales mark in a weekly period, outside of Drake’s Views in 2016. 

The album, which would also go on to win the Grammy for best rap album, was Wayne’s sonically richest yet, resisting any easy regional pigeonholing, as Wayne served up something for everyone. The ambitious C3 produced three major Hot 100 hits, as the extraterrestrial double-entendre of “Lollipop” featuring the late Static Major topped the Hot 100 for five nonconsecutive weeks, while the T-Pain-assisted strip club anthem “Got Money” and the blazing-though-hookless “A Milli” also cracked the top 10. (Who could forget Wayne’s day in the life on set for the “A Milli” visual?) Even the cover art, featuring Wayne as a baby with face tattoos, has lived on as iconic. 

Tha Carter III encapsulated everything Wayne had to offer from his versatile repertoire. Whether he was barring up against Jay-Z on “Mr. Carter” or playing rapper-doctor on “Dr. Carter,” he jumped around with ease. Weezy even offered social commentary on political topics like President Bush’s inaction when it came to Hurricane Katrina relief in his hometown (on “Tie My Hands”) or condemning the criminal justice system and reverend Al Sharpton (on “Don’t Get It”). Lil Uzi Vert would later say of Weezy: “When I heard Tha Carter III, I knew Wayne was the greatest rapper alive.”

It’s tough to believe if you didn’t live through it, but Lil Wayne had possibly the greatest peak of any rapper ever circa Tha Carter III. While rap titans Kanye West, Jay-Z and Eminem were dominating, Weezy had perhaps the highest level of respect and general approval rating of his peers, fans and critics at that point. Ye himself called Wayne his “fiercest competition” while on stage at the ‘08 BET Awards. “You scare me, man, every time you spit,” West said.  

This was Wayne’s MVP Award and championship run, like 2012 LeBron James or ‘92 Michael Jordan. The New Orleans dignitary was a player that was automatically on fire anytime he stepped into the booth. Seriously, everything he touched seemingly turned to gold. Established as the millennials’ rap superhero, Lil Wayne led from the top of the food chain – even when clashing with his superstar peers on supercharged posse cuts like “Swagga Like Us” (No. 5 Hot 100).

With Weezy at the peak of his powers, he was essentially minting new hitmakers on radio seemingly on a weekly basis, 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 Hot 100, and Wayne’s memorable verse – and thoughts on the economy – remain a staple in rotation for DJ sets at bars across the country. All artists wanted a piece of Lil Wayne at this point, as his Wayfarer sunglasses, tattoos and purple Bape jacket became imagery ingrained in American pop culture. 

At the top of the game, Wayne tested the depths of his artistry with his newfound guitar skills when he zagged into the rock-leaning Rebirth. He was probably a few years too early on the rock star wave that came to the hip-hop mainstream with the next generation of rhymers like XXXTENTACION, Lil Uzi Vert, Trippie Redd and Playboi Carti. Nonetheless, the album debuted at No. 2 on the Billboard 200, while Weezy’s six-string lessons on the pummeling shout-along “Prom Queen” still made it to the Hot 100’s top 15.

In the midst of the commercial peak of his career, Lil Wayne was also thinking about the next generation of rappers. By the end of the 2000s, he’d sign two artists who would take what he’d built with Young Money to the next level in the following decade — Drake and Nicki Minaj — as well as fellow up-and-comers like Tyga and Jae Millz. The We Are Young Money compilation album arrived in Dec. 2009 to assist in spotlighting some of the talented artists running behind Wayne. The project ended up spawning hits like the raunchy polyamorous posse cut “Every Girl” and the Lloyd-assisted crowd-pleaser “Bedrock,” which hit No. 2 and provided early memorable solo moments for both Drake and Nicki.

An eight-month jail stint on Rikers Island in NYC for a gun charge forced the always-moving Lil Wayne to sit down for much of 2010, as he pressed pause for the first time in a long time and temporarily took off the “Best Rapper Alive” crown. Still, the motivational horns of “Right Above It” with Drake managed to invade the Hot 100’s top 10 from behind bars, following a premiere from Hot 97’s Funkmaster Flex. High school football players across the U.S. made the Kane Beatz-produced beat the soundtrack to their highlight tapes while the girls walking the hallways updated their Facebook statuses in unison to Wayne’s feel-good, “Life’s a beach, I’m just playing in the sand” bar. 

It didn’t take long for Wayne to get back on track following his release from Rikers. Tha Carter IV’s lead single “6 Foot 7 Foot” – which felt like the cousin to C3’s “A Milli” – gave him another top 10 entry on the Hot 100, and earned his seat back at the rap council. Teaming up with friend DJ Khaled has long been a fruitful formula for Wayne, and they also scored another hit heading into the summer of 2011 with “I’m on One” alongside Drake and Rick Ross. Meanwhile, a pair of C4 advance singles – the smoky, bar-heavy “She Will” and the acoustic ballad “How to Love” – showcased the duality of Wayne’s artistry, and both reached the Hot 100’s top five. 

After several delays, Tha Carter IV finally arrived to close out the summer on Aug. 28, 2011, and the fourth installment in the decorated series nearly missed out on being Wayne’s second release to reach the million mark – moving 964,000 total album units in its first week while debuting at No. 1. While the project wasn’t as acclaimed or beloved as C3, it showed that even Wayne’s B-game could still surpass most hitmakers on their best day. 

Much of the 2010s resulted in creative frustration for Lil Wayne, who was entrenched in a nasty $51 million lawsuit with his mentor Birdman and Cash Money Records over financial compensation. The two parties would end up settling in June 2018 after three years of litigation, which finally cleared the way for the much-delayed Tha Carter V. But even during that in-between period, Wayne was still active, making ways on the feature front by reuniting with Chris Brown on “Loyal” – which reached the top 10 and spent nine months on the Hot 100 in 2014 – and earning assist wins on DJ Khaled’s No. 1 hit “I’m the One,” French Montana’s “Pop That” and Chance The Rapper’s “No Problem,” and scoring another top 10 hit of his own with the Drake- and Future-assisted “Love Me.”

At the same time, Wayne poured time and energy into building his proteges Drake and Nicki into stars in their own right, as he popped up on their albums for guest verses and remixes whenever needed. While Drizzy and Minaj took the baton and ultimately surpassed Weezy’s pop stardom in their own wildly successful crossover careers, they still always pay homage to Wayne as the GOAT, and continue shouting him out for giving them a chance and helping them achieve their rap dreams.

As Wayne’s hot streak began to cool down in the mid-2010s, so did his commercial visibility. However, another chapter of Tha Carter was still enough to push the rap world’s hype into overdrive once again.

The seven-year build-up leading into C5 was going to be nearly impossible for Wayne to match, as the project hit streaming services on his 36th birthday in 2018. Though the LP didn’t live up to the quality of previous installments, Tha Carter V was still a major commercial success – debuting at No. 1 with 480,000 units moved and netting Wayne the second-most first-week streams ever (behind Drake’s Scorpion), while also making him the first artist to launch a pair of debuts in the Hot 100’s top five (“Mona Lisa” featuring Kendrick Lamar and “Don’t Cry” with XXXTENTACION). 

Funeral scored Weezy another No. 1 album to start the 2020s off on the right foot, but none of the tracks stuck on the charts, as his days as a leading hitmaker appeared to be behind him.  Nonetheless, in an era where remixes feel formulaic and hollow, Wayne shined bright 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 Hot 100 (while peaking at No. 2) during the COVID-19 pandemic. These days, Lil Wayne’s phone is still buzzing as one of the most in-demand feature artists in all of hip-hop – including for the next generation, with younger rap stars like Polo G, Cordae, Trippie Redd, YoungBoy Never Broke Again and J.I.D. tapping Wayne for verses this decade – but instead of his Sidekick, it’s just an iPhone.

Three decades since the self-inflicted gunshot wound at home that nearly took his life, Wayne has scored 186 Hot 100 hits – fifth most of any artist in chart history – and won five Grammys. Weezy’s timelessness and wordplay wizardry has him serving up razor-sharp verses with eccentricities that are often imitated but could never truly be duplicated. Maybe he really was an alien all along. 

Read more about the Greatest Pop Stars of the 21st Century here and check back on Friday when our No. 20 artist is revealed!