17 Throwback Photos From Lil Wayne’s Legendary Career

Lil Wayne has given us countless eras since making his debut, so it's hard not to get nostalgic about his iconic 2000s and early 2010s run. The New Orleans rapper made history with Hot Boys days alongside Juvenile, B.G. and Turk, saw even more success with the first few Tha Carter albums, and became so much more with the launch of Young Money Entertaiment, TRUKFIT and his several other ventures.

Rap-Up pulled together 17 throwback photos that showcase some of the best moments from Lil Wayne’s legendary career. There are appearances from other Cash Money Records favorites, snapshots of him at awards shows, and a few rare glimpses of him backstage, in the studio or simply being himself. Scroll through for a reminder of why, decades later, Weezy is still your favorite rapper's favorite rapper.

1. 1999 Source Awards

File under: Things we’d love to see come back. In 1999, the Hot Boys, Birdman and Mannie Fresh attended the Source Awards in white tees and Cash Money chains. Juvenile took home Single of the Year for “Ha,” so the matching outfits paid off.

2. Cash Money Attending “The Jenny Jones Show” In 2000

While Lil Wayne is practically synonymous with his countless face tattoos these days, there was indeed a time before all that ink. In this shot, the New Orleans rapper was backstage at “The Jenny Jones Show,” where he also joined his Cash Money peers for a live rendition of “Tha Block Is Hot.”

3. Bulletproof Memorial Day Weekend Celebrity Basketball Game In 2004

The 2004 Bulletproof Memorial Day Weekend celebrity basketball game brought plenty of star power both on and off the court. Above, Weezy poses courtside with Gotti of the duo Boo & Gotti.

4. 2005 BET Awards

Back in the mid-2000s, it felt like every rapper was rocking BAPE, and Lil Wayne was definitely no exception. He showed up to the 2005 BET Awards red carpet in a purple hoodie and black-and-white Bapestas.

5. LeBron James’ 21st Birthday Party

Most of us can only dream of the “Lollipop” hitmaker performing at our birthday parties — let alone attending LeBron James’ birthday celebration. Above, the two legends posed together at Cleveland’s House of Blues. Safe to say, the NBA legend’s tenure with the Cavaliers gave us some truly special moments.

6. 2007’s Hot 97 Summer Jam

Lil Wayne and Fat Joe shared the stage for 2007’s Summer Jam. The two previously united on “Make It Rain” on the Bronx native’s Me, Myself & I. As Weezy spat in the chorus, “Yeah, I'm in this b**ch with the Terror.”

7. Lil Wayne's 25th Birthday Party

If you need more proof that parties in the 2010s were a different breed, take a look at this photo of Rick Ross, Gunplay, T.I., DJ Khaled and plenty more turning up with Lil Wayne for his 25th birthday. It’s also worth mentioning the “Love Me” rapper's celebration took place on a yacht!

8. 2008 MTV Video Music Awards

As much as we have zero intention of bringing back the vest-over-a-tee trend from the 2000s, it surprisingly worked in Lil Wayne’s favor at the 2008 MTV Video Music Awards. Plus, he ended up taking home a Moon Man for Best Hip Hop Video, so he clearly did something right.

9. 51st Annual Grammy Awards

Here’s an iconic picture of four GOATs hanging out backstage at the 51st Annual Grammy Awards. At the 2009 ceremony, Lil Wayne teamed up with T.I., JAY-Z, Ye and a very pregnant M.I.A. for “Swagga Like Us.” The track deservedly took home Best Rap Performance By A Duo Or Group. Weezy F Baby himself cleaned up pretty nicely, too; he grabbed Best Rap Album for Tha Carter III, Best Rap Song for “Lollipop” and Best Rap Solo Performance for “A Milli.”

10. 52nd Annual Grammy Awards

“I got ice in my veins, blood in my eyes / Hate in my heart, love in my mind,” Lil Wayne rapped at the start of his performance of “Drop The World” at the 52nd Annual Grammy Awards. Yes, he was so locked in during that era that he performed two years straight. His set didn’t go without some star cameos, either: Travis Barker pounded the drums, Eminem stepped onstage midway through the song and Drake walked out last for a powerhouse rendition of “Forever.”

11. Super Bowl XLIV After-Party

Also in 2010, the New Orleans Saints squared off against the Indianapolis Colts, so Young Money showed up big to support Lil Wayne’s hometown team. In the photo above, Weezy posted up with Nicki Minaj, Gudda Gudda, Short Dawg and Jae Millz at Miami’s Dolce Nightclub to celebrate after the Saints clinched the win 31-17.

12. Chris Paul’s PBA Celebrity Bowling Invitational In 2012

At his 2012 PBA Celebrity Bowling Invitational, Chris Paul linked up with Reggie Bush, Nelly and Lil Wayne. Honestly, it's about time celebrities got back to playing sports other than basketball and football again.

13. 53rd Annual Grammy Awards

For the awards show in 2011, Lil Wayne scored an Album of the Year nod for his contributions to Eminem’s Recovery, while Nicki Minaj competed for Best Rap Duo/Group Performance for Ludacris’ “My Chick Bad.” The Young Money artists arrived at the red carpet with their “Senile” collaborator, Tyga, and amusingly didn’t even pretend to coordinate outfits. Lil Wayne wore a navy cardigan and dress pants while Minaj arrived in head-to-toe leopard and Tyga had on a white blazer.

14. The Los Angeles Lakers vs. Chicago Bulls Game

If you’ve followed the No Ceilings artist for a while, you know he’s a die-hard Los Angeles Lakers fan. During a Lakers vs. Chicago Bulls game in 2011, Weezy ran into Ye, who was clearly there repping for Chi-town. Unfortunately for Lil Wayne, his beloved Lakers took a tough 88-87 loss that night at the then-known Staples Center.

15. Posted At The Peabody Hotel In 2005

Speaking of throwbacks: Lil Wayne’s sideburns were lethal back in the day! Here, he posed shirtless at Orlando’s Peabody Hotel. The Grammy Award winner’s giant “M.O.B.” chest tattoo and Cash Money ink on his stomach have obviously gotten plenty more company in later years.

16. Macy’s Launch Event For TRUKFIT In 2012

The New Orleans legend took a brief promotional tour to celebrate the launch of TRUKFIT, his streetwear brand inspired by his passion for skateboarding. At the Beverly Center in LA, Weezy teamed up with pro-skater Stevie Williams for a fan meet-and-greet event.

17. DIRECTV's 7th Annual Celebrity Beach Bowl

Although the Saints didn’t make it to the 2013 Super Bowl, Weezy was still hyped that the big game happened in New Orleans at Caesars Superdome (then called the Mercedes-Benz Superdome). On Super Bowl weekend, he participated alongside Snoop Dogg and other stars in DIRECTV’s Celebrity Beach Bowl.