Juwanna Mann (2002)

Juwanna Mann follows the story of Jamal Jeffries, the reigning 'bad boy' of basketball, whose undisciplined on-court antics land him out of the league and without any prospects. Financially strapped and untrained in anything but basketball, Jamal comes up with a plan so outrageous it just might work: dress up like a woman and try out for the woman's basketball league. To his surprise, he makes it, but now the real challenge begins - to cease being Jamal and start new life as Juwanna. Matters become even more complicated when Juwanna realizes that he is falling for his teammate Michelle, who shows him that there is more to women than meets the eye.