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Before Lil Wayne goes to jail, here are 13 photos reminding us of his legacy

Lil Wayne

When it comes to iconic moments rapper Lil Wayne has many and the photos to prove it…

For Lil Wayne, 2020 was a year that landed him in more media headlines than he may have intended.

From his record-breaking mixtape No Ceilings 3 and his political interests to new gun charges and possible prison time, the legendary rapper has had a memorable year.

Why is Lil Wayne facing a decade+ in prison?

Lil Wayne was federally convicted on possession of drugs and a firearm while flying from Los Angeles to Miami in December of 2019.

On December 11, 2020, Weezy pleaded guilty to the possession of the firearm where his trial was projected to take place in early January of the new year.

Given the fact that the rap legend has pled guilty to the charges as a convicted felon, the offense has the potential to land Lil Wayne in prison anywhere from 10-15 years in prison.

With thoughts and prayers that Lil Wayne will be able to beat this case and continue exercising his passion as one of the greatest rappers ever, it is important to acknowledge the iconic moments that he created throughout 2020 and before.

With the latest information being that Lil Wayne could face 10 to 15 years in prison for drugs and a firearm charge, we decided to review 13 iconic moments of the rap GOAT, to honor him before what could be a devastating curtain call on his time in the spotlight.

1. We’ve been here before

Lil Wayne photographed by Carlo Allegri after leaving a court hearing in a firearms possession case in Manhattan, NY – February 09, 2010

In 2009, rapper Lil Wayne pleaded guilty to a felony charge of attempted gun possession. He was sentenced to one year behind bars. According to CNN, Tuneci was arrested in New York City in 2007 after police found a .40-caliber pistol on his tour bus.

After serving 8 months of his sentence, Lil Wayne was released early for good behavior.

In a statement to the New York Times, Lil Wayne’s defense attorney argued the law barring convicted felons from ever owning a gun again may not be constitutional:

Carter is charged with possessing a gold-plated handgun in his luggage on a private plane. There is no allegation that he ever fired it, brandished it, used it, or threatened to use it. There is no allegation that he is a dangerous person. The charge is that because he was convicted of a felony in the past, he is prohibited from possessing a firearm.

Although the Supreme Court has not yet decided the constitutional question, Justice Amy Coney Barrett recently wrote an appellate dissenting opinion in which she stated that ‘Absent evidence that he either belongs to a dangerous category or bears individual markers of risk, permanently disqualifying [a felon] from possessing a gun violates the Second Amendment.

2. The photo of GOATS Lil Wayne and Kobe Bryant

The 2020 BET awards, which took place in June, was an important moment for not only Lil Wayne but for Black culture in light of Weezy’s highly spirited tribute performance for the late great NBA legend Kobe Bryant.

Weezy performed an updated version of his classic song ‘Kobe Bryant’ that he released after the LA Lakers victory over the Orlando Magic in 2009.

BET Awards 2020

Considering the fact that the song was a loose single that had not been featured on any Lil Wayne projects initially, the inspired performance showed his respect and gratitude for Kobe.

Photo by Kenneth Cappello via

Furthermore, the two have expressed their respect for one another on many occasions for the similarities they have regarding each other’s work ethic and desire for the mastery of their respective crafts.

This Lil Wayne photo with the late great Kobe Bryant shows game recognizes game.

3. Lil Wayne and Birdman photographed at Lil Wayne’s Funeral listening party

MIAMI, FLORIDA – FEBRUARY 01: Birdman and Lil Waune attend Lil Wayne’s “Funeral” album release party on February 01, 2020 in Miami, Florida (Photo by Gerardo Mora/Getty Images for Young Money/Republic Records)

By the end of summer 20’, Lil Wayne took a trip back into his vault of classic albums and mixtapes to re-release No Ceilings. It is perhaps one of his most iconic mixtapes to date making it available on all streaming platforms.

But it also makes us think about Lil Wayne’s career through the years, from starting with Hot Boys, to signing with Cash Money Records, and all of his agreements and disagreements with Birdman over the years.

This Lil Wayne photo was taken in 2020, during a less contentious time in the relationship of these two rap moguls. And it serves as a staunch reminder of the prowess of the two of them as a pair.

4. His run with the Hot Boys

Juvenile & Lil Wayne photographed by Erin Patrice O’Brien during a portrait session – 2000

Let’s throw it back real quick. This photo of Lil Wayne and Hot Boys OG, Juvenile, reminds us of the humble beginnings of Lil Tunechi.

He looks young and naive to the undercurrents of the rap world. Before he could fly, Wayne had to run with this group.

And run they did. Running so fast it helped propel Wayne to the heights he now achieved.

5. Mama Wayne knows best

Lil Wayne & his mother photographed by Sarah A. Friedman during a portrait session for Blaze Magazine – February 2000

There are countless bars where Lil Wayne thanks his mama. This photo of the great rapper and his mother reminds of why he’s dedicated so many songs to her.

It’s just me and my Momma how it’s supposed to be/And I make sure she paid like she wrote for me…

– Lil Wayne “Cry Out (Amen)

5. Lil Wayne with Nicki Minaj and Drake

(Left to Right) Lil Wayne, Nicki Minaj, and Drake at the BBMAS 2017. Photo by Kevin Mazur via Getty Images.

Ah, everyone’s favorite love triangle.

Drake, Nicki, and Lil Wayne have given us some inspired music over the years. And this photo is a reminder of the star power this trio presents.

Young Money, from when many of us remember them all cooking it up in the studio together. Though they may have grown apart, this photo will live on as iconic forever.

6. “We Are the World” recording sessions

Lil Wayne performs at the “We Are The World 25 Years for Haiti” recording session held at Jim Henson Studios on February 1, 2010 in Hollywood, California. Photo by Kevin Mazur via WireImage.

Lionel Richie, Wyclef Jean, and Lil Wayne stand here in this iconic image during recording sessions for “We Are the World 25 for Haiti.”

Lionel Ritchie, of course the songwriter for the original 1985 hit “We Are the World” is an icon himself. Wyclef Jean’s Haitian ties are well-founded. And Lil Tunechi’s recording acumen solidifies this photo as evergreen and iconic.

7. A reminder of Wayne keeps it Bape’d up


Let’s not forget who the king of this drip sh** is. Here, Wayne models the Bape x Ugg collab.

Everything Bape. Lil Wayne also stands as the GOAT in these throwback jawns of him in the og Bape.

Lil Wayne photographed by Lester Cohen at the 2005 BET Awards in Hollywood, CA – June 28, 2005

Lil Wayne, no matter what one thinks about him or his music, has swag in abundance.

8. Lil Wayne and Curren$y

Per Currensy himself, him and Wayne are tight af.

They don’t look the slightest bit sober, nor in Wayne’s case, like they give af about that. Rap and culture legends.

This photo is iconic because of the duo’s relationship and how authentically it captures Wayne in his natural habitat.

(Courtesy of Randall Slavin)

Blink-182 and Lil Wayne’s collab-tour should stand as a model for any group looking to collab with another.

Their sounds are starkly different, yet they were able to collaborate on an entire tour. And while they may have had their problems along the way, this image sticks in your head the moment you see it.

10. He was a skater boy…

LAS VEGAS, NV – AUGUST 20: Lil Wayne performs at the 1 OAK Nightclub at The Mirage Hotel & Casino on August 20, 2012 in Las Vegas, Nevada. (Photo by Bryan Steffy/WireImage)

An acronym for “The Reason U Kill For IT,“ TRUKFIT hit the mainstream in 2012. At first it was little weird to see a rapper other than Lupe fiasco step into the skateboarding space, but now it’s just a part of the culture.

Lil Wayne even pulled up to his deposition rocking his the brand. Talk about LEGENDARY.

Now one of the most recognizable skate boarding brands out there, TRUKFIT is definitely one thing to remember about the icon.

11. I can’t feel my face…

Lil Wayne and Juelz Santana circa unknown

The I Can’t Feel My Face era was a good one. An unmatched duo, Juelz Santana and Lil Wayne changed the course of hip hop with this legendary mixtape.

It’d be really nice to get a part two. But we know how that goes…

12. Good ‘ol Uncle Snoop

Snoop Dogg & Lil Wayne photographed by Kevin Mazur while attending the Direct TV 7th Annual Beach Bowl in New Orleans, Louisiana – February 02, 2013

Homies, rivals, family are all words that identify these two. Snoop has always had a high respect for the New Orleans rapper. In June, Snoop actually pressed Wayne about going on a VERZUZ battle.

“That Verzuz battle, when they gon’ get you in there?” asked Snoop. “You the young GOAT! You birthed the second generation of rappers. Dem is yo babies out there. You deserve to be in the race.”

“If they start me, they ain’t gon’ stop me,” Weezy replied. “They gon’ have to ring the bell, ‘Tune stop!’ I can’t stop.”

Snoop even compared Tunechi’s rap career to the basketball career of the late Kobe Bryant. “Kobe played half his life in basketball,” he told Wayne.

“Half your life has been in rapping. I just wanna see you in there because I love what you do and I know what you bring to the table. You the young GOAT, you understand me? A lot of people say that they GOATs, but they not GOATs.”

Hopefully, this is still something we’ll see before Lil Wayne goes to his prison sentence hearing.

13. Where it all began

Lil Wayne photographed by Marcus Hänschen during a portrait session for Murder Dog Magazine at age 15 in Hollywood, CA – 1997

At this point in his career, it is clear that Lil Wayne is at the point in his career where he is releasing bodies of work with the sole purpose of fulfilling his love for rapping.

Regardless of how one feels about the Young Money CEO, there is no denying the fact that Lil Wayne is one of the most talented and enigmatic artists to ever grace a microphone in music.

Looking at the severity of Lil Wayne’s gun possession case and possible jail time there is a great deal of uncertainty regarding the future release of music and most importantly his freedom.

How do you think 2020 contributed to Lil Wayne’s rap career? Where do you think he will land in the GOAT conversation when it’s all said and done?

Additional edits by Claude J. Easy and Conrad Hoyt.