I don’t have the birthtime for Amy Winehouse, but she was born 9/14/1983 in Londres, UK. I am working with a noon chart because she is a famous person, although now her problems are getting more press than her talent. Winehouse has Venus/Mars in Leo trine Neptune and possibly the Moon as well. This gives her that amazing star quality at best, or an almost shameless thirst for attention (reeling from the Pluto transit). Pluto demands transformation; a time to discard habits and people (like addictions and characters that support them). A Pluto transit can also symbolize losing something very valuable (like a loved one or a career). The more willing a person is to bend with the transit, the less devastating the damage. Attitude is everything (prayer can help).
Winehouse is being energetically supported to get through this, but of course there’s “free will”– which means it’s her choice if she tunes into the support or succumbs to old habits. In the noon chart, Pluto is finishing with her Sadge Moon/Neptune and Saturn is transiting her midheaven (career point). Saturn (discipline, limits, fear, karma) is then heading toward her Sun- which can be a low health period for a person. This will demand she clean up her act or she will risk serious hazards. Since Saturn will also be in opposition to Uranus (inspiration, disruptions) in the sky, this heightens the pressure cooker sensation for her. It is critical transiting Neptune (escape, creative) opposed to her natal Venus, is a time for her to make music. Ideally she will find a mediation instead of obsessions that foster drama and escapism.
If she is born later than noon, her moon is in Capricorn, so Pluto (Lord of the Underworld) has only begun its lessons. Her rehabilitation is essential and she will either open the door to transformation or close the door inviting tragedy.
Winehouse has the Sun/Mercury. Virgos are typically neat, orderly and have specific diet/health routines. But unfortunately addictions are routines. Some Virgos create chaos so they then can then create order. Because of this, there is great potential for Winehouse to turn her life around. However, potential is never a guarantee; it takes focused action to be realized.