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Which Year was Lil Wayne the Best Rapper Alive?

Lil Wayne’s domination of the rap game started out of necessity. By 2005, Cash Money Records, the label Weezy had been signed to since he was 11 years old, was in a very bad spot. Over the prior two years, pretty much all of its star talent left the fold: the members, minus Wayne, of the Hot Boys; and the label’s in-house producer Mannie Fresh. 

Wayne, who turned 25 in the fall of that year, was at that point not even the most successful member of his own group—Juvenile had gone quadruple platinum with his 1998 classic 400 Degreez, while Weezy’s 2002 release 500 Degreez managed only gold. 

But with his back against the wall, Wayne defied the odds. Even before everything fell apart at the label, he had begun experimenting. In 2002-3, he released a mind-blowing seven mixtapes with his Sqad Up crew. The projects showed Wayne growing and experimenting, trying out different ideas in a low-pressure environment, over other peoples’ beats

If you weren’t listening to mixtape Weezy back then, you would have been forgiven for thinking that Lil Wayne wasn’t up to carrying Cash Money on his back once everyone left. His 2004 album Tha Carter, recorded prior to Fresh’s departure, showed some improvement, sure. But it gave no indication that its maker would soon shoot to the very top of the rap game.

Tha Carter II, released at the tail end of 2005, was a quantum leap forward. On track seven, Weezy made a startling claim: he was, the title boasted, the “Best Rapper Alive.” To the surprise of almost everyone, the album made a strong case. 

The hip-hop universe that Tha Carter II was released into in December, 2005 was one that belonged to the South. T.I. and Jeezy were at their commercial and artistic peaks. Houston rap exploded into the mainstream following the release of “Still Tippin’” in late 2004. 50 Cent’s G-Unit (which, no doubt sensing the trend, added Nashville rapper Young Buck to its roster) was still a dominant force, but there was a sense that their glory days were coming to an end. 

But emcees from below the Mason-Dixon line were still fighting for respect from a critical establishment that was holding on to New York-centric standards of lyricism. It was a problem Wayne addressed head-on. 

“So many doubt ‘cause I come from the South,” he rapped on “Shooter.” “But when I open up my mouth, all bullets come out.” 

Were those lyrical bullets potent enough to vault Weezy F. Baby (“now the ‘F’ is for FEMA,” he joked on “Feel Me,” one of Tha Carter II’s few nods to the hurricane that devastated his hometown just months before the album’s release) to the vaunted status of “best rapper alive,” as he claimed? It definitely happened at some point during his historic 2005-9 run. But when? And when did it stop? Here’s our attempt to determine just that, year by year.


Wayne shocked the world with Tha Carter II, it’s true. Pitchfork spoke for a whole lot of people when they looked at his progress since Tha Carter and proclaimed, “Who knows what’s happened since then, but damn has he learned how to write.” 

The Lil Wayne of Tha Carter II is confident, smart, and able to use his voice in all sorts of ways that weren’t immediately apparent in his earlier work. Some of the improvement, no doubt, is due to no longer having an endless supply of Mannie Fresh beats. Instead, Wayne raps over a variety of different kinds of compositions, from a mix of producers both well-known (Heatmakerz, Cool and Dre) and less so (Tmix and Batman). 

To go along with Tha Carter II, Wayne also dropped a mixtape called Dedication. Similar to its proper album partner, it showed Weezy F. hitting a new peak in terms of ideas, confidence, and freedom. He knew it, too. “Young Money, and the leverage is deep,” he rapped. “I am better than I ever been—that other shit was weak.” 

Wayne’s output in 2005 was a warning that he was no longer a Cash Money B-teamer. Instead, he fully belonged in rap’s upper echelon. However, he wasn’t quite at the top of the pile. That year, a resurgent Common would gain new energy from collaborating with a fellow Chicagoan, Kanye West (now known as Ye). Their combined efforts would result in the album Be, which received critical acclaim and was also a commercial hit, going gold in just a few months.


The promise shown on Tha Carter II really blossomed the following year. Dedication became a series with the release of Dedication II, helmed like the first one by DJ Drama. Wayne also joined forces with his label boss/surrogate father Birdman for the album Like Father, Like Son

Both of these projects were stunning. Dedication II featured Wayne jumping from subject to subject like the wildest game of hopscotch you’ve ever seen. “I waited on my turn to burn, can I get a light / Little dog, bigger bite / Jackson 5ive, little Mike / Can I get a mic or a mic and a half / That The Source owe me? Shout out to the editor staff,” went one such section on “Sportscenter.” Weezy also got political on “Georgia… Bush,” a vicious attack on the then-president for his response to Hurricane Katrina. 

As for Like Father, Like Son, it featured some of the same top-tier rapping from Wayne, but in the context of catchy, hook-laden songs like “Stuntin’ Like My Daddy” and “Leather So Soft.” Some critics found the subject matter a bit limited, but that didn’t stop the project from debuting in the top 10.

Lil Wayne’s 2006 output again firmly placed him in rap’s elite. But T.I. narrowly edged him out by releasing King, the album that contained his career-defining hit “What You Know.” Despite the loss, the year taught Wayne a lesson: he could release a ton of material, and not suffer a drop in quality. It was a lesson he would take to heart.


In a 2006 interview with Complex, Wayne explained that his strategy was “being on everybody’s singles.” He reads off a huge list of artists he has recently collaborated with: Destiny’s Child, Chris Brown, Justin Timberlake, Mya, Kelly Rowland, Timbaland. 

In 2007, Wayne would take that work ethic into hyperdrive. He didn’t put out any official albums that year—his only solo release was the classic mixtape Da Drought 3 (about which more later). But he did so many guest verses, and put out so many songs that ended up on random mixtapes, that one writer was able to put out a list of the top seventy-seven songs Wayne rapped on just in that year. Think about that for a second. Has there ever been a rapper who put out that much material, of such high quality and with such a varied list of people, in a single year?

Much of the material came from mixtapes that collected material recorded during sessions for Tha Carter III. Those sessions had Wayne following his muse wherever it led, and it led some pretty strange places: the woozy “I Feel Like Dying,” the Auto-tuned weirdness of “Prostitute.” It was this Wayne, the one who would go to outer space while singing about lean, that would end up having the biggest influence on the next generation of eccentric Southern rappers like Young Thug. HotNewHipHop wasn’t exaggerating when they headlined a 2019 article ‘Lil Wayne’s “I Feel Like Dying” Altered The Trajectory Of Hip-Hop.’

It wasn’t all flange weirdness, though. There was plenty of rapping rapping in 2007. And a lot of the best of it was found on Da Drought 3. Wayne took everything he’d been working on over the past few years and sharpened it to a fine point. He jumped from couplet to couplet, changing topics and rhythms at will. It was like watching an expert tightrope artist. 

You can hear it on his retake of DJ Khaled’s “We Takin Over,” a song that he absolutely owned in its original version as well. But this remix is a true thing of beauty, moving on a dime from boasts to threats to nods to Stephen King, somehow finding time to quote “When Doves Cry,” drop a “dese nuts” joke, borrow Scott Storch’s yacht, and unironically exclaim “Yikes! Yeeks!”

On the same tape, he famously murdered Jay Z on his own shit with a freestyle over Hov’s “Show Me What You Got.” “When it comes down to this recording, I must be LeBron James if he’s Jordan,” Wayne spit, making it perfectly clear who he was talking about. 

In 2007, there was absolutely no competition. Even Wayne’s discards were fire enough to perform on awards shows, and popular enough that his label rushed out an EP of the most popular ones. He was, without question, the best rapper alive.


All of the work Wayne did in 2007 paid off the following year. All of his scores of songs served to build anticipation for Tha Carter III to a fever pitch. So when it finally came out in the summer, it sold a million copies in its first week. 

The project’s lead single “Lollipop,” released a few months prior, was Wayne’s highest-charting song to date. The song, which featured and was co-written by Static Major (who tragically died just before its release), put Wayne’s Auto-tune experiments in a catchy, commercial framework. But it was the single’s flip side “A Milli” that would in some ways have the more lasting impact. Over a simple but memorable beat by Bangladesh, one that would show up on mixtapes and radio freestyles for years to come, Wayne laid out some absolute fire rapping. 

The rest of Tha Carter III was stellar as well, but there was no resting on the album’s laurels for Wayne. He continued delivering incredible guest verses on songs like “Swagga Like Us,” “Turnin’ Me On,” and “Can’t Believe It.” And right before the year ended, he dropped a third volume in the Dedication series. There was again no question: Lil Wayne was continuing his run as the best rapper alive.


In October 2009, Wayne pleaded guilty to a gun charge stemming from an incident where a gun was discovered on his tour bus in New York City. He was sentenced to a year in jail. It stopped the workaholic rapper in his tracks, and serves as a sad but convenient point to place the end of his absolute dominance of the rap game for the prior five years.

Prior to that, though, Wayne was not slowing down, pending charges be damned. In 2009 he released another top quality mixtape, No Ceilings. It was, sadly, the last project with Wayne at the absolute peak of his powers. 

But while Wayne may have not released a ton of material in 2009, that year served to set up his continuing relevance in the rap game. It was that year, after all, that his label Young Money, would sign the two artists who would dominate for the next decade-plus, Nicki Minaj and Drake.  

All of that is not quite enough to grant Wayne a final best rapper alive crown, though he certainly was in the running. But the competition, including a resurgent Jay Z, was just too fierce. 

To look back on Lil Wayne’s 2005-9 run is to see an artist pushing, experimenting, and finally arriving at the top of his game. Seemingly everything he tried worked, and even his wildest experiments (in some ways, mostly his wildest experiments) ended up having an untold influence on the shape of hip-hop to come. He was releasing work at a volume that is hard to fathom, even in our new content-is-king age. He was a master at finding new ways to use his voice. Even while releasing literally hundreds of songs during this period, he never sounded repetitive, or like he was running out of ideas. It was a true miracle, and a run that we’re unlikely to ever see again, from Wayne or anyone else. 

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