Songfacts®:

• This song details nightlife on Cyprus Avenue, which is identified in the song's first line ("down on Cyprus Avenue"). Cyprus Avenue is a real place in Van Morrison's hometown of Belfast, Ireland. It's also the title and subject of another Astral Weeks song.
  
  There are a few characters in this song, but they all revolve around Madame George, who gambles, parties, and possesses something that requires tossing out a window during a police raid.
  
  For most listeners, it seems obvious that Madame George is a drag queen. Morrison himself has denied this, explaining it's just a mishmosh of multiple people he'd known.
  
  Still, many (including legendary rock journalist Lester Bangs) have seriously questioned Morrison's claim. In addition to the obvious juxtaposition of the feminine identifier "madame" (basically the French equivalent of "Mrs.") with the man's name "George," Morrison sings:
  
  In the corner playing dominoes in drag
  The one and only Madame George
  
  It's also possible that it's simply a woman named George, as throughout the song the character is referred to as "she" and "her." Then again, it may simply be a show of respect to a transsexual's preferred gender.
  
  Whatever the character's sexual identity, he or she comes across as a goodhearted ne'er-do-well who also carries a lot of sadness.
• The version of the song appearing on Astral Weeks is nostalgic and melancholy and accentuates the tragic aspects of this mysterious Madame George, but the original vision of the song was quite different. It was first entitled "Madame Joy" and was more upbeat and celebratory. In 1973 on the T.B. Sheets album, Morrison released that original Astral Weeks version, recorded on September 25, 1968.
  
  It appears Morrison ultimately made the right call with which version to release first, because it went on to become one of the most critically respected songs in popular music history. Many consider it Morrison's best, including Morrison himself.
• Sinéad O'Connor mentions Madame George in her song "Black Boys on Mopeds":
  
  England's not the mythical land of Madame George and roses
• At 9:45, this is the longest song on Astral Weeks.
• On that train from Dublin up to Sandy Row
  
  Dublin is capital city of Ireland. Sandy Row is a street in Morrison's hometown of Belfast, Northern Ireland. A train ride from one to the other takes a about two-and-a-half hours.
• The cool night air like Shalimar
  
  Shalimar is a perfume produced by the Guerlain perfume company and invented in 1921 by Jacques Guerlain. According to the perfume publication Fragrantica, Shalimar has long been known as a "bad girls'" perfume worn by women who shamelessly live the nightlife lifestyle.
• In Celtic Crossroads, Morrison says he had a clairvoyant grandmother named Joy, and the song may have originally been about her. He doesn't know why he switched the title to George. His grandmother Joy lived in the area that "Cyprus Avenue" is based on.