50 Cent watched all of Jim Sheridan's films to prepare for his role. His personal favorite was The Boxer (1997).
50 Cent hired an acting coach but Jim Sheridan had the woman removed from the set. Sheridan told 50 "If this fails, it won't be because you can't act. It's because I didn't direct you right."
Samuel L. Jackson was offered the role of Levar but turned it down. He told an interviewer that while he liked 50's music, he did not feel that 50 earned the right to star in a film by Jim Sheridan. However, Jackson later co-starred with 50 in Home of the Brave (2006).
Bono introduced Jim Sheridan to 50 Cent because Sheridan expressed a desire to meet and work with 50.