What I do know is that she has spent a lot of time exploring the role of gender, and as a female to male hetero/bi crossdresser she certainly fits the profile.
The Eurythmics was big in the 1980's, which saw the birth of a large number of crossgender artists, including Boy George, Dead or Alive and -- let's admit it -- Freddie Mercury.
But must of these were gay. Lennox is more like a female counterpart to David Bowie as Ziggy Stardust, which brings her closer to most crossdreamers.
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An online friend got a message from another online Indian friend, who asked whether her song "No More I Love You's" says something about the transgender condition.
It definitely demonstrates Lennox' sympathy for male to female crossdressers and drag artists.
The Sweet Dreams video is a clear example of art that breaks down the traditional divide between masculine and feminine symbols and expressions. There can be no doubt that the Lennox of this video is a beautiful and sexy woman. The fact that she dresses up as a man and uses manly mannerisms does not change this.
If you compare the video above with the one below, it is easy to see how unbalanced our cultures are when it comes to gender. The male to female crossdressers in this later video also combine male beauty with cross-sexual attire and mannerism. It is a fair guess that most people will find them absurd and far from sexy.
This reflects a culture that deep down looks upon the masculine as something positive and the feminine as something weak and unasked for.
The ballet scene is placed in a secret dungeon or club in the late 19th century, a period of amazing sexual and cultural exploration, and with increasing understanding for the diversity of human sexuality and gender expressions. It was not to last. The German Nazis and the American psychiatric establishment soon found ways of pushing the "deviants" back into their closets.
The video is also interesting for another reason. It seems to me to depict two different types of crossdressing.
The ballet dancers gives a drag performance, and as drag queens often do they parody the female stereotypes. In other words: They are not really trying to appear as real women, but as someone who is more feminine than any woman who has ever lived.
Drag queens are most often androphilic, and will just as often identify as feminine gay men as women.
The male audience, being dressed up by seducing women, are more like gynephilic crossdreamers. Some part of them is dreaming of being a woman, which is why they are unable to resist the enforced crossdressing. On the other hand, these guys have no training in appearing feminine, which is why they look as men in drag, even when they are not.
This video does not tell us who are the true women, the drag artists or the crossdressers, or Annie Lennox for that matter.
In fact, the strange, uncanny, laughter seems to tell us that this play of gender expressions is nothing but an artificial game, and that the whole dichotomy of feminine and masculine is misleading.
Indeed, Annie Lennox herself plays Luna, the Moon, who throughout her feminine 28 day cycle reflects both the stereotypical masculine (rational enlightenment and the full moon) and the stereotypical feminine (the darkness of emotions and the unconscious feminine), as well as every position in between.
Note also how Lennox is replaced by a man at the very end.
The second version of the song, a performance from the Letterman Show, reveals how even a liberal like Letterman is unable to take this gender challenge seriously. Lennox shows her displeasure.
Lennox is certainly a pro-gay, anti-fundamentalist and liberal, and she tries to make room for a more generous view of what it means to be a man or a woman. As she says: The words cannot capture what this is about:
I used to have demons in my room at night
Desire, despair, desire
So many monsters
No more i love you's
The language is leaving me
No more i love you's
The language is leaving me in silence
No more i love you's
Changes are shifting outside the words