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http://www.youtube.com/watch?v=WLrrFxXZ3rk
To me the message is it's cool and funny for a man to wear a dress IF you are actually: a straight man; big enough to be physically intimidating; capable of fighting effectively; putting one over on those unfair "ladies nights" bars; and have a ton of friends who are regulars at said bar.
I don't see that translating into an actual trans person or cross dresser going into a random country bar and not being hassled.
I agree there's a tinge of homophobia in the "You better watch what you drink" line. That said, I think it has more to do with the cliches around the "known crossdresser" (i.e. everyone knows Bobbi = Bobby") that are similar, but different, from the cliches about transsexual women that Julia Serrano critique.
(Serrano points out portrayals of transsexual women tend to be the "pathetical transsexual," who's hopelessly masculine no matter how hard she "tries" to be a woman; and conversely the "deceptive transexual" who's too successful and "fools" people in to thinking that she's someone "she's actually not." In both cases, these cliches fundamentally dispute that transsexual women are women.)
In the case of the "known crossdresser" is seems there's two cliches, both of which revolve around disbelief: disbelief that a man could convincing appear and act "like a woman;" and disbelief that a man would want to be seen as, and treated as, a women. I.e. effemina-phobia, which as Serano points out, is all too common, even in feminist thinking. (Or one reason femme lesbians don't always get a lot of respect either.)
So from Milton Berle to Monty Python to Rudy Giuliani, portrayals of crossdressers tend to be of ones who are "unconvincing." For comedy, part of it is probably simply the visual incongruity (make-up and beard shadow), since visual incongruity is a staple of all sorts of comedy. OTOH, the "art of transformation" is something that people often seem fascinated with. I get colored polish put on when I go for pedicures, and that means I end up telling a lot of women at the salon that I do drag. If they see some pictures, usually the reaction is along the lines of: "OMG, I can't believe that's you!" Interestingly, female impersonators were extremely popular during the late 1800s/early 1900s, often playing the biggest, and best, theaters in town, and there was a similar fascination. (FWIW, most of these female impersonators were hetero, as far as we can tell, and no one really questioned that.)
But OTOH being intentionally "unconvincing" does seem to be often done for distancing reasons — i.e. the crossdresser doesn't really want to be seen as, treated as, a woman, which is a lot less threatening to people's comfort in the gender binary. I noticed both straight guys who crossdress for Halloween and gay who drag it up for Pride, both seem give cues -- subtly or overtly -- that they're "all male" no matter how "realistic" an appearance they may have. Admittedly, it may be projection on my part. Learning to blend in as a woman is something that took a bit of work on my part (learning nuances of body language, patterns of speech etc.), and it often hard for someone who's male-bodied to speak in a way that perceived as someone female-bodied.
Are the song/video perfect? By no means. But it was intriguing to me that both Vassar and his record company thought that the song was worthy being the lead single from the album -- and that the subject matter wouldn't be off-putting to listeners (or at least enough to prevent it from being a hit).
@ calixi — Yeah, the scantily clad young women were annoying. I didn't bother to comment on it because it's so pervasive.
@ Reba — That's very cool. Just a good reminder that things aren't always what we think they are.