Having won two Grammy Awards, attracted considerable attention in the English-language media, and appeared in several Hollywood films, Latin popular singer Rubén Blades has been much discussed as a crossover, that is, as an artist who, with a well-defined audience (in this case Hispanic), produces work that appeals in addition to another audience (here the audience for mainstream American popular music). El Gran Combo de Puerto Rico, in contrast, continues to appeal to its traditional Hispanic audience and remains the undisputed leader in popularity with that audience. A comparison of a piece by El Gran Combo with one by Blades suggests ways of thinking about the relationship of both to their audiences and to each other and ways in which musicology might approach such questions in specifically musical terms. Blades is seen not to be crossing over from one audience to another but to represent transformations in his Hispanic audience, which is itself crossing over to become increasingly imbued with Anglo culture while remaining rooted in its own traditions.