After years of struggle, during which he was often told he was unsuitable for the classic, this actor began gaining recognition for his performances on Broadway in the 1990s. Ruben Santiago-Hudson scored on the New York stage in three projects--as cornet player Buddy Bolden alongside Gregory Hines in the musical "Jelly's Last Jam" (1992), as Canewell, the harmonica-playing amateur philosopher, in August Wilson's "Seven Guitars" (1996), for which he won a Tony Award, and in the title role of "Henry VIII" for the New York Shakespeare Festival in 1997. After his turn in the Wilson play, interest for his services grew in Hollywood. Santiago-Hudson was cast alongside Al Pacino and Keanu Reeves in "Devil's Advocate" (1997) and he landed a regular role in support of David Caruso in the CBS drama "Michael Hayes" (1997-98).