I’ve had to listen to this song several times just to be sure it was real and not just an insane figment of my imagination. But alas, whether I like it or not, it is real and I’m the one who has been charged with the task of attributing words from the English language to this strange composition, which suddenly seems limiting. So, please excuse my casual tone just this once, because I’m going to have to forgo the formal conventions of a review in order to even come close to adequately describing this song.
“Bobby With an I” is about a cross dresser. Bobby is a man’s man during the week, but he turns into Bobbi when the work week is through. He makes such a convincing woman that “you better watch how much you drink/He might look better than you think.” Right.
Despite how others may feel about the somewhat subversive topic, it is actually a redeeming quality of the song. While it’s treated very lightly here, it is still likely to offend the sensibilities of some disapproving country music listeners. However, what offends my sensibilities is the execution of the song in general.