2009 Highlights: Staying humble but still riding high off of his 2008 Man of the Year win, Wayne sideswiped a potential rap battle with 50 Cent by refusing to engage the G-Unit General, but continuing to do what put in him a preeminent position: make music and perform it for the people. His I Am Music Tour with the likes of T-Pain and Keri Hilson was a huge critical and commercial success. But Wayne’s biggest live show would happen in February at the Grammy Awards in Los Angeles. Weezy, Jay-Z, Kanye and T.I. stole the program with a historic performance of “Swagga Like Us” only for Wayne to return to the same stage later to rep for his hometown with “Tie My Hands.” Wayne was nominated for eight Grammys and left with three, including Best Hip-Hop Album.

February was also a pivotal month in that his musical collaborator and Young Money clique member, Drake, released the mixtape So Far Gone. Drake, our #8 Man of the Year nominee, went on to be the hip-hop rookie of the year with two hit singles and two Grammy nominations. Drake officially became a Young Money artist in late June. Wayne took his entire camp — which includes another budding rap star, Nicki Minaj — out on tour this summer for the America’s Most Wanted Music Festival. That outing and his I Am Music Tour earned a combined record-breaking tally of over $42 million.

Outside of music, Wayne had plenty to keep him busy. BCD Music Group, an independent distribution company based in Texas, put him in the middle of a lawsuit against mixtape king DJ Drama, while Wayne was in full support of a lawsuit to stop the distribution of the documentary “Tha Carter”, which was produced by QD3. In yet another lawsuit, Wayne sued producer Mali Boi for failing to clear a sample of singer Karma-Ann Swanepoel’s “Once.” The folk singer sued Wayne for copyright infringement for use of “Once” on Wayne’s “I Feel Like Dying.” Of course, Wayne’s most troubling court proceedings dealt with his gun-possession case. In October, the acclaimed performer pleaded guilty to gun possession. Weezy is scheduled for sentencing in February, where he is expected to receive one year in jail.

Despite impending prison time, Wayne’s appeal has reached well into the mainstream. He’s had guest appearances on tracks from Madonna to Drake to Cash Money member Jay Sean. Weezy also appeared on ESPN multiple times (also serving as a celebrity blogger for the sports channel), went bowling with Katie Couric for a primetime special and had his own “Behind the Music” episode.