At one point in Hip-Hop history, fans were divided on who was the best rapper in the game. While many iconic MCs have come and are present, the mid-2000s served as a time when Lil Wayne made it clear that he believed he was the best rapper alive.

The “best” status is relative to individual preferences, but it did not stop the Louisiana-born rapper from making a claim and even writing a song highlighting the sentiment.

Lil Wayne officially hit the music scene in the mid-1990s as a member of the Hot Boys with fellow band members – Juvenile, B.G., and Turk. The four rappers produced hits like “I Need a Hot Girl” and “Rock Ice.” Wayne would launch a solo career in 1999 with his debut album, “The Block is Hot.”

However, it wouldn’t be until 2004 that the then 22-year-old rapper would gain increased popularity with the release of “The Carter,” which turned into a series of albums, catapulting the rapper into Hip-Hop superstardom.

In 2012, he would take the Billboard title as the male artist with the most entries on the Billboard charts, with 109 songs, only being knocked down by one-time label mate Drake.

Going beyond the mic, the now 40-year-old rapper would accumulate a massive net worth by diversifying his business ventures. These ventures include serving as the head of Young Money Records, penning a book, and creating a skater shoe line.

Although Lil Wayne has been able to garner so much success throughout his career, he found himself in hot water with the IRS at points in his career. He was, however, able to rise above the turmoil with the help of a colleague and additional contender for the best rapper alive status, Jay Z.

Tax Issues

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