I am not going to go into a great biographical analysis but an am going to simply let the photos and the Astrology speak for itself. But first: the photos
is the reincarnation of Judy Garland
Both were superstar performers and highly accomplished artists well before their 21st birthday.
The first thing that jumps out, right away, is Judy's Sun at 18 Gemini conjuncting Amy's Ascendant at 17 Gemini. Their Moons are one degree apart, too, although in different signs -- Judy 29 Sagittarius, Amy 0 Capricorn. Two very important and very TIGHT aspects and we've barely examined the charts. We also see Judy's Mars (18 Sagittarius) in opposition to her natal Sun and, therefore, parked right on Amy's Descendant in the 7th House of Partnership. Amy's 20 degree Leo Mars also trines Judy's very closely, both in FIRE.
To compound the significance of these planets, Amy's North Node at 20 Gemini conjuncts Judy's Sun and her South Node, therefore, conjuncts Judy's Mars.
And to rev up the firey planet's significance even greater, Amy's Sun (21 Virgo) is in a square with Judy's Mars and also, of course, Judy's Sun, too . . . so Amy's natal Sun makes a T-Square with this Sun-Mars opposition of Judy as well as a T-square with her own Moon Nodes.
Planets on the angles are important (and karmic, too) and in addition to the Mars Placement on Amy's Descendant, we also find Judy's natal Neptune at 13 Leo conjunct Amy's I.C. Judy's Neptune is placed, therefore, in Amy's 4th House -- the natural home of the Moon
. . . and Amy's natal Neptune (26 Sagittarius) is conjunct Judy's natal Moon at 29 Sagittarius.
Next up, Judy's Mercury at 0 Cancer opposes both her Moon (off by one degree) and Amy's (an exact opposition).
Another karmic planet is Saturn and in past life matches we would expect to see some action between one person's natal Saturn and personal planets and/or angles of the other. We have that, as well . . . Judy's Mercury forms an almost exact trine to Amy's natal Saturn (1 Scorpio) and Judy's natal Saturn (0 Libra) squares Amy's Moon.
Another interesting parallel -- both have two Retrograde planets. Each has Retrograde Mercury and each also has one of her traditional "relationship planets" retrograde, as well . . . Judy has a Retrograde Mars and Amy has Retrograde Venus (which is in a conjunction with her natal Mars 23/20 Leo).
This is a LOT and the aspects are very tight . . . ideally we would see some action between Amy's chart and Judy's Ascendant but Judy's birth time is listed at 6 am so it is possible this time is an approximation and not exact. All in all, a fairly tight synastry between these two once in a generation artists.
Therefore, my belief is that Amy Winehouse is Judy Garland, reborn.