Since the late ’90s, Lil Wayne has been one of Hip-Hop’s more captivating figures. Born and raised in New Orleans, Wayne began his rap career as a preteen on Cash Money Records, releasing a studio album alongside B.G. as part of the group the B.G.’z. Appearing on subsequent group and solo releases from the label, Weezy was included as a member of Cash Money’s super group, Hot Boys, alongside Juvenile, B.G., and Turk.
Lil Wayne quickly became a fan favorite for his standout performances on hit Hot Boys albums Get It How U Live! and Guerrilla Warfare, creating anticipation for his solo debut. Released in 1999, Tha Block is Hot was a runaway success, peaking at No. 3 on the Billboard 200 and topping the Top R&B/Hip-Hop Albums chart. The album established Wayne as a star in his own right, laying the groundwork for a career that has come with unprecedented peaks and daunting valleys, but never a dull moment. From reaching the heights of his craft with his Tha Carter series to being in musical purgatory, Weezy has seen and done it all, making his historic run all the more impressive.
With thirteen solo studio albums and several collaborative albums, compilations, and mixtapes, Weezy’s accolades make him one of rap’s most accomplished artists of all-time. Breaking ground for himself and other artists under his tutelage—and never cheating the game—he has earned Lil Wayne his place in the pantheon of cultural icons.
Wayne’s latest landmark moment comes as a byproduct of a life lived, as the rapper turns 40 years old this week (Sept. 27). Continuously evolving over the years, Weezy doesn’t appear close to retirement anytime soon, routinely reminding us that his eye remains fixated on greatness. However, with nearly three decades in Hip-Hop under his belt, there’s very little left to prove.
To help him commemorate 40 years of life, VIBE highlights 20 definitive Lil Wayne songs that document his journey from youngest-in-charge to musical icon.
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"Tha Block Is Hot"
After years of sharing the spotlight, Lil Wayne stepped to the forefront with this blistering lyrical salvo, which doubled as the title track to his debut solo album. Released in 1999, the track included contributions from Hot Boys brethren B.G. and Juvenile, but saw Wayne as the central figure, asserting himself as more than a mere cog in the Cash Money machine. Bringing listeners to the streets of New Orleans with potent imagery, “Tha Block is Hot” minted Weezy as a breakout star and is widely regarded as a bonafide classic.
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"F**k Tha World"
Glimpses into Weezy’s introspection were captured in this soul-bearing testimonial, which saw the rapper addressing his tumultuous life journey and the its toll taken. Produced by Mannie Fresh, this somber composition retains an air of triumph, with Wayne’s defiant never-say-die attitude shining through with every bar.
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"Shine"
Proving that the platinum success of his solo debut was no fluke, Lil Wayne returned the following year with his sophomore effort Lights Out, which was powered by this celebratory jam. Featuring appearances from Hot Boys and production by Mannie Fresh (who also blesses the hook), this track saw the young upstart and his New Orleans clique basking in the lap of luxury.
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"Go D.J."
Following defections by Juvenile, B.G., and Turk in the early 2000s, Lil Wayne who embraced his role as the face of Cash Money and heir to the throne. After a stride backwards with his underperforming third studio album, 500 Degreez, Weezy showed considerable progression as a lyricist on his follow-up effort Tha Carter. Deemed his most complete body of work at the time, Tha Carter included the hearty party-starter “Go DJ.” The single found Wayne and longtime collaborator Mannie Fresh relying on their innate chemistry once again. The result: a classic that marked a return to form and ultimately altered the trajectory of his career.
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"I Miss My Dawgs" feat. Reel
With his former group having diminished in the wake of 500 Degreez, Lil Wayne‘s longing for brotherhood was expressed on this impassioned deep cut on Tha Carter. Featuring Reel and a bluesy backdrop by Mannie Fresh, the track found Wayne reminiscing on the Hot Boys‘ formative years as a unit and memorable moments he holds dear. Putting his pride and ego to the side, Wayne professed his love for Juvenile, B.G., and Turk on this contemplative selection.
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"Fireman"
Having built up momentum as one of the most skilled lyricists in the South, Lil Wayne upped the ante with Tha Carter II, an album that established him as one of music’s hottest artists. With Mannie Fresh’s departure from Cash Money as well, Weezy retooled his approach with new boardsmen like Doe Boyz on his lead single, “Fireman.” An amped-up anthem, the song went double platinum and coincided with Weezy’s rise to rap’s man of the moment.
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"Best Rapper Alive"
Jay-Z ‘s retirement from rap had the unintended consequence of emboldening Lil Wayne to vie for the throne. After declaring himself “the best rapper alive since the best rapper retired” on “Bring It Back,” Weezy’s confidence only grew with Tha Carter II the following year. The bruising “Best Rapper Alive” made his intentions crystal clear; Wayne threw down the proverbial gauntlet of being Top Dog. His words proved prophetic, as fans and pundits began to openly lend credence to his lofty claims.
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"Hustler Muzik"
Lil Wayne hooked up with TMIX for this sonically rich ode to life as a rolling stone. Speaking from the vantage point of a hustler striving to create financial freedom, Weezy conveys the stress that comes with the territory. While lacking the charting success of the other singles released during that period, “Hustler Muzik” further solidified Wayne’s evolution as a songwriter, accounting for one of the more beloved numbers in his catalog.
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"Cannon"
Lil Wayne refused to take his foot off the gas after Tha Carter II, making a firm case for being the best rapper on the planet with his Dedication II mixtape. Hosted by DJ Drama, Dedication II is filled with verbal highlight reels, but Weezy’s performance on “Cannon” found him reaching the apex of his forces. More than a freestyle or mixtape cut, this song marked a moment in time. It also served as the nexus of a cultural shift that would impact the rap landscape for years to come.
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"Stunnin Like My Daddy" feat. Birdman
In 2006, Lil Wayne and Cash Money CEO Birdman looked to shovel dirt over the competition with their collaborative album Like Father, Like Son. The album earned gold certification and included the hit single “Stunning Like My Daddy,” a song emblematic of both their close bond and the renewal of Cash Money’s reputation as a force to be reckoned with.
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"I'm Me"
Lil Wayne‘s massive rise in popularity after the release of Tha Carter II and Dedication II resulted in eager fans salivating for new material. During the recording process for the wildly-anticipated Tha Carter III, tracks intended for the album were leaked, including this boastful number. “I’m Me” finds Weezy asserting his dominance as the overarching face of Hip-Hop. Originally titled “1000 Degreez,” the track finds Tunechi delivering some of the hardest quotables of his career, traversing over the brooding production with the countenance of a executioner commissioned for duty.
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"I Feel Like Dying"
“I Feel Like Dying” is another notable leak from Tha Carter III sessions. Detailing the rollercoaster ride of drug use and drug addiction, the track was a precursor to a rock-influenced Hip-Hop wave that Wayne helped introduce. Unfortunately, the song garnered a lawsuit against Weezy over an uncleared sample, and the song never received an official release.
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"Lollipop" feat. Static Major
For rappers in 2008, transcending Hip-Hop to become a mainstream darling required a seismic single, which only a shortlist were able to produce. Lil Wayne added himself to this rare class with the syrupy groove that catapulted him to the top of the Billboard charts for five weeks straight. Featuring the late Static Major and produced by Deezle and Jim Jonsin, “Lollipop” won a Grammy Award for Best Rap Song and remains one of his most successful songs.
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"A Milli"
Looking to channel his mixtape magic into to an official release, Lil Wayne merged the two worlds successfully with Tha Carter III‘s “A Milli,” offsetting the pop appeal of “Lollipop” and catering to his core. Produced by Bangladesh, the song inspired a flawless performance by Wayne, who flowed with nimble precision over the infectious track. Peaking At No. 6 on the Billboard Hot 100, the track became one of Weezy’s most popular records to date and won the Best Rap Solo Performance at the 2009 Grammy Awards.
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"Mr. Carter" feat. Jay-Z
After years of verbally jousting with Jay-Z on his quest for lyrical supremacy, Lil Wayne elevated himself to mutually-beneficial stature. Weezy and Hov would finally connect on Tha Carter III’s “Mr. Carter,” a track that was culturally interpreted as a “passing of the torch.” Trading bars on the song’s third verse, two legends with a shared last name put their rivalry aside for a historic moment in time. Hov’s presence on the was a subtle feather in Wayne’s cap, affirmed his music reign.
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"Got Money" feat. T-Pain
Lil Wayne and T-Pain collided for this lively number, which finds the pair both delivering auto-tuned vocals atop a backdrop produced by Play-N-Skillz. The song finds the two superstars waxing poetic about the joys of spreading the wealth, resulting in it becoming an anthemic number, particular in the nightlife scene. Released as the third single from Tha Carter III, the song peaked at No. 10 on the Billboard Hot 100, has reached triple-platinum certification, and remains one of Wayne’s stronger collaborative efforts.
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"6 Foot 7 Foot" feat. Cory Gunz
Lil Wayne reconnected with “A Milli” producer Bangladesh on this monstrous single for Tha Carter IV. Recruiting Young Money signee and prolific spitter Cory Gunz, the two spitters matched wits on the song’s final verse, resulting in an otherworldly meetings of the minds. Attempting to outpace and outclass each other, Weezy and Gunz ran roughshod atop a sample of Harry Belafonte’s “Day-O (The Banana Boat Song),” turning in a masterclass of emceeing and a Top 10 hit.
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"She Will" feat. Drake
After the release of Tha Carter III, Lil Wayne refocused his efforts on building his Young Money roster. In the subsequent years, he would ink multiple stars, including Nicki Minaj and Drake, the latter of whom he’d form one of the more potent rap tandems of all-time. Of their numerous Wayne-led hits together, few have had the success of this heater, which peaked at No. 3 on the Hot 100 and remains the second-highest charting hit of the veteran’s career.
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"Uproar"
Lil Wayne‘s unprecedented run hit a snag amid a lengthy legal battle with Cash Money Records, resulting in continued delays of his Tha Carter V album for years on end. After finally reaching a settlement, Weezy got back to business, making his return to the charts. “Uproar” found him reconnecting with producer Swizz Beatz, attacking a sample of G Dep’s 2001 hit “Special Delivery.” Lil Wayne displayed no signs of rust from the layoff, laying down one of the hottest records of the year and bookending 20 years of classics.
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"Let The Beat Build"
In addition to the succession of hit singles from Tha Carter III, the album contains some of Lil Wayne‘s most inventive material to date. Challenging the borders of his artistry yielded varying results, but his efforts proved to be ingenious on “Let The Beat Build.” Rhyming over a Deezle production, the song saw Wayne dismantling an instrumental created from scratch. Positive reception to the song’s originality and Weezy’s lyrical performance further fed his desire to be acclaimed as one of the greatest to ever pick up the mic, and constituted its inclusion with his greatest works to date.