Lil Wayne's 20 Best Songs: Critic's Picks

Lil Wayne didn't stumble upon fame -- he bulldozed his way into the music industry. Before blossoming into a cerebral lyricist, at age 15 Wayne joined the Hot Boys alongside B.G., Turk and Juvenile. By 17, he unleashed his debut album The Block Is Hot, which debuted at No. 3 on the Billboard 200 and later earned platinum status.

Unsatisfied with his early accomplishments, Lil Wayne developed an insatiable appetite for success, and released a flurry of mixtapes at a frenetic pace. From his Dedication series to The Drought Is Over, Wayne rocketed to the apex of rap with his prolific work ethic. While he was crushing instrumentals on the mixtape front, he also was obliterating what was left of the mainstream circuit.

After proving his lyrical prowess on Tha Carter and Tha Carter II, Lil Wayne morphed into a full-fledged superstar with his release of Tha Carter III. Thanks in part to his tuneful single "Lollipop" -- which became his first No. 1 single on the Billboard Hot 100 -- Wayne's Tha Carter III sold over a million copies during its opening week.

Though he encountered several roadblocks, including severe delays, the elusive Tha Carter V will be released next Friday (Sept. 21), concluding his fiery 14-year run with the decorated series. For now, let's take a walk down memory lane and reflect on some of Weezy's best tracks below.

20. Lil Wayne - “I'm Single” - I Am Not a Human Being

Opening with the nearly muted pieces of conversations with Nicki Minaj, “I'm Single” is a relaxed anthem for anyone newly single: “I’m Single... I ain’t trippin’ on nothin, I’m sippin’ on something.” Wayne takes the time to lament on an old relationship, all while calmly celebrating his new freedom. The track originally appeared on the mixtape No Ceilings, but quickly earned its spot on I Am Not A Human Being. The slower warped beat was an updated, unusual take for the rapper, but telling of Wayne’s growth by 2010.

19. Lil Wayne - “Ice Cream Paint Job” - No Ceilings

Another iconic example that no beat is safe with Wayne. As he says, “I’m all over this ice cream beat like sprinkles.” This was the pinnacle of mixtape Weezy, showing him at his most thoughtful level of technical ability, but not once seeming like he was trying that hard to do so.

18. Lil Wayne - “Walk It Out” - Da Drought 3

At one point, Wayne was the undisputed king of freestyles and remixes. There was no beat he couldn't conquer, and even on tracks that seemed to need no help, Wayne could always somehow give them second life -- the best example probably being "Walk It Out." Wayne took the song behind the dance craze, and presented himself another opportunity to casually deliver verse after verse, declaring, "If they talkin, most likely I’m what they talkin’ ‘bout."

17. Lil Wayne ft. Bobby Valentino and Kidd Kidd - "Mrs. Officer” - Tha Carter III

With the help of the ever-smooth Bobby Valentino, Wayne delivers a slow jam for the ladies, all while emasculating all the cops who have ever done him wrong. Complete with a cultural reference to Rodney King, Wayne lays back on this one, making it one of his smoothest songs, and another testament to his witty metaphor skills.

16. Lil Wayne - “Georgia … Bush” - Dedication 2

Up until this point, Lil Wayne’s legacy had very little to do with any of his political opinions, but "Georgia … Bush" was a beautiful testament to his political capacity. After the catastrophic 2005 Hurricane Katrina swept the south, the rapper took aim at President George W. Bush, who was criticized for slow response to the natural disaster, and as Wayne puts, “let em kill all of our troops.”

15. Lil Wayne & Birdman - “Stuntin’ Like My Daddy” - Like Father, Like Son

Long before the lawsuits, the accusations, and the deteriorating label, Birdman and Wayne ruled the south. "Stuntin’ Like My Daddy" is a staple of the southern rap movement, with an infectious hook and some of the hardest bar for bars between two rappers, maybe ever -- and somehow also one of arguably the best Wayne verses as he comes in for his third round.

14. Lil Wayne ft. Drake - “Believe Me” - Tha Carter V

After Lil Wayne proved himself as the best out, he started working on an emcee worthy enough to pass the torch. And that’s where Drake comes in. By "Believe Me," Drake was fairly established, but the Weezy affiliation still seemed connected to his name, and parts of his flow still seemed a little borrowed from his predecessor. On "Believe Me," the two sound comfortable exchanging, building on each other verse for verse, and proving that Wayne was as good of a mentor as he was a rapper.

13. Lil Wayne - "I’m Me” - Tha Carter III

The first thirty seconds of "I’m Me" are basically a killer compilation of all of the best Cash Money affiliates’ ad-libs and assertions, from the Birdman bird call to the “it’s Cash Money Records man, a lawless gang.” Then what ensues is the closest a rap song can get to a power ballad -- a song with Wayne showing off as hard as he can go on a laid-back flow. He put it best when he said, “This is Tha Carter III, the New Testament.” The song spans a full five minutes, with Wayne not backing down once, trading in a faster flow for tact and lyrics, and flexing his iconic use of double entendres more than once.

12. Young Money ft. Gucci Mane - “Steady Mobbin” - We Are Young Money

In the mid 2000s it was nearly impossible to compete with Weezy on any mid-tempo beats. And while Gucci Mane definitely held his own, Wayne makes it clear it’s his song with three of the hardest verses, adding Gucci Mane as an exclamation point. The cut came from the first-ever Cash Money Records joint album, marking a time when the label was at its peak, before the lawsuits and online back-and-forths. As for “Steady Mobbin,” its largest legacy might be one of the most iconic Weezy questions it gave us: “Okay you’re a goon, what’s a goon to a goblin?”

11. Lil Wayne - "Hustler Musik” - Tha Carter II

Catching up on a beat that’s a bit more melodic than Weezy’s usual portfolio picks, "Hustler Musik" is the rapper's own version of a more classic New York sound. The combination makes for a Weezy track that delivers life advice and lessons in a way that’s a little softer than some of the others.

10. Lil Wayne ft. Reel - “I Miss My Dawgs” - Tha Carter

In a showcase of a slightly more sentimental side, Wayne delivers one of the most relatable songs of his catalog -- a somber, cutting, and simple ode to lost friends and family, and fading friendships and relationships. On any streaming platform, the comments below “I Miss My Dawgs” are flooded with messages to lost connections and relatives, a testament to the way the track hit with listeners.

9. Lil Wayne - “Tha Block Is Hot” - Tha Block Is Hot

For a generation of fans, this debut solo single was the first track they heard from the scrappy 17-year-old Atlanta rapper. No longer just a hype man for the older guys on the label, a much-younger Lil Wayne proved his prowess with this classic track. Wayne’s voice is as raspy as ever, and the video shows him baby-faced, still surrounded by the big kids on the label. But in the next few years, Wayne would stand alone at the top.

8. Lil Wayne - “Swag Surfin” - No Ceilings

In the same vein of the iconic "Walk It Out" freestyle, Wayne flips the switch on something that seemed to need no additives. Over the iconic "Swag Surf" beat, Wayne begins with a flow similar to the original, but adds the exclamation points we expect from him at this point: clever wordplay ("watch me shooting to the bank, I’m a money pistol"), nearly four different flows on one track, and a consistency that lasts for the entirety of the five minute song.

7. Lil Wayne ft. Static - “Lollipop” - Tha Carter III

At the height of the Auto-Tune movement arose the ultimate Auto-Tune masterpiece: “Lollipop,” an iconic Lil Wayne track based around an incredibly un-subtle innuendo. The song and video immediately became a major mainstay on the spin cycle at TRL -- at a time when that meant a lot -- with cameos from R. Kelly and a very young Tyga. Adding to its early 2000s glory, the track also became the #1 selling ringtone of 2008, bumping out of millions of flip-phone speakers across the nation. Fittingly, the song is one of only two of Weezy’s chart-topping tracks on the Hot 100.

6. Lil Wayne - “Best Rapper Alive” - Tha Carter II

The pressure that surrounds dropping a track entitled "Best Rapper Alive" is obvious. But for Weezy, the self-inflicted challenge was another opportunity to prove, that in 2005, he might have really been the best rapper alive. Switching effortlessly between at least two different flows, Wayne saunters over the DJ Khaled beat, adding "fucking" to the list of words the F in Weezy F Baby stands for.

5. Lil Wayne ft. Cory Gunz - “6 Foot 7 Foot” - Tha Carter IV

For Wayne, "6 Foot 7 Foot" served as a reminder to many, that he still had it. The 2011 track was on the tail-end of his nearly half-decade long reign as hip-hop king, and the rapper went out with as much power and tactful lyricism as he came in with. “Young money militia and I am the commissioner, you don’t wanna start Weezy cause the F is for finisher.” Wayne absolutely destroys the militaristic beat, pulling back on speed at points, only to emphasize absolute speed and dominance in his bars moments later.

4. Lil Wayne - “Fireman” - The W. Carter Collection 2

Within the four-minute span of "Fireman," Wayne rapid fire delivers some of the goofiest, most quotable Wayne lyrics of all time, and then delivers another Wayne staple again when he comes through with an undeniable hook. At one point, he spits “Ain't nobody fuckin' with me, man /He-man, ski mask, spendin' next week's cash, he fast, and I don't even need a G pass,” a play on words so casually brilliant only “the best rapper alive” could pull it off.

3. Lil Wayne - “Let The Beat Build” - Tha Carter III

“Let The Beat Build” is a concept track at its core, a swaggering soulful rap ballad that takes one of the most recognizable samples of all time and pairs it with the then “best rapper alive.” Its brilliance is -- as almost always -- in the way that Wayne can match, and then add, to a beat. For nearly the first three-fourths of the track, Wayne stays right on top of the booming Eddie Kendricks’ sample, delivering bar after bar smoothly, building at the same natural, hypnotic pace of the beat. Then, with only about a minute left, he dances off of it, quickly and cunningly dropping some of his most explosive bars, almost as if to prove it’s not just the Deezle and Kanye West produced beat that’s leading this track. It’s a lesson in how to amplify something that already seems perfect, a beat that’s so iconic it’s the official beat of ciphers and freestyles, yet it is and always will be Wayne’s: “As I hit the kill switch, that’s how you let the beat build bitch.”

2. Lil Wayne - “Go DJ” - Tha Carter

"Go DJ" was a single that marked the end of Lil Wayne’s era as a rising rapper, and solidified him as top ranking on the Cash Money Records lineup, the Lil Wayne we know him as now. It’s the pinnacle of mixtape Wayne meeting the more commercial Wayne, the incredibly bright beginning to his nearly five-year reign as the undisputed best emcee in the game. Not only did it mark the end of Weezy’s climb to the top, but it was the end of Wayne’s working relationship with famed producer Mannie Fresh, who stopped collaborating with the rapper after Tha Carter. The two had more than enough time to make their mark as a pair, and “Go DJ” is still a likely play at the club on any given weekend.

1. Lil Wayne - “A Milli” - Tha Carter III

At one point, it seemed like everyone in America had memorized every word to "A Milli" — that may be a hyperbole, but there seemed to be genuine national sense of awe over the bars on this track. For four minutes, Wayne goes uninterrupted on wordplay, all while executing a flow faster than some of his more recognizable mid-tempo tracks -- not once sacrificing speed for lyricism. The song was a ubiquitous hit the whole year, playing non-stop on the radio, at parties, and on TV -- but somehow ten years later, it still doesn't feel old.