Anne Boleyn gets my vote.
As some earlier posts mentioned, Henry's pursuit of her bordered on what, in modern terms, we would call sexual harassment. I think Anne was pressured into a relationship she felt was unsafe to refuse. And I think much of her subsequent demanding and self-aggrandizing behavior was anchored in her conviction that, if she was going to have to accept the importunities of a man she did not love, she at least had a right to get something from the bargain.
And what a foul bargain it turned out to be, after all. Her survival came to depend on something over which she had no control -- having a male child. And the cost she paid for failing was to go to her death, knowing her brother was suffering the same fate under the same false calumny of incest, and probably assuming her daughter had little chance of ultimately surviving.
Excellent points, tsarfan. For all the reasons you've stated, I think Anne had it "the worst" and consequently I'd have not liked to endure the same level of what must have been the constant, unending, overwhelming stress of trying to outwit her enemies and placate the King at the same time. Especially since, unlike Catherine Howard, Anne was innocent of the charges brought against her.
Catherine Howard was a knowing player in the game which brought her downfall. I feel sorry for her because she was an immature little thing raised to dazzling heights by a lecherous old man, and lacked the wisdom and guidance allowing her conduct herself in accordance with her station. But, at the risk of sounding brash, her time in the sun was short, her death quick. She ranks second as the wife I'd have least like to have been.
Jane Seymour. I think she's much more clever and calculating than generally given credit. It takes a cold woman to wed a man a day after he's beheaded his previous wife. Had she not given birth to a son before dying shortly after childbirth, I doubt Henry's memories of her would have been so "rose-colored." Third in line only because the idea of dying as she did seems horrible, given the primtive state of medicine then.
Catherine of Aragon, although the wrongly maligned first wife, still maintained some shreds of her dignity and retained the affection of many (if not most) of the King's subjects. Life with chilblains cannot have been plesant, though.
Fourth.
Now to the last two....
Catherine Parr, a woman whose character I admire, certainly had the unfortunate luck to be the primary nurse for Henry's horrible oozing leg. However, he seems to have been much more mellow with age, and they appeared to have been fairly companionable. She was a bit of an old hand at dealing with older husbands, of course, before she married the King. Her strong religious beliefs could easily have resulted in her own arrest. Where I feel sorry for her is the whole scandal involving Elizabeth and Thomas Seymour years later.
Thus, by elimination, the wife I'd have most liked to be? Anne of Cleves, obviously. Marriage gets her out of her dull brother's pumpernickel court; she has the singular good fortune not to arouse the king's ardor and thereby gets a pass on having to perform her marital duty with the old lout. By being smart enough to be acquiescent to his wish to divorce, Anne earns the King's friendship as a "sister", a couple of manor houses, a nice fat allowance, and lives contentedly as a woman of means in a country of which she has grown fond.
