The Rapper: Freeway
The Stunt: In December 2008, the Philly rapper launched his "Month of Madness" and released a new song every single day for 31 days straight.
How Well Did It Work? If you didn't know that Freeway was a great rapper before this series started, you knew it once it ended. If nothing else, it solidified Free's presence on the Internet and helped him build up his buzz so that he could release his new album, Philadelphia Freeway 2, in May 2009.