Which fragile, eccentric teenage film queen was actually the most talented?

Connie Francis.

I will go out on a limb and say that Molly Ringwald brought a complete naked level of realism to her roles that the others did not. She is completely believable in Sixteen Candles - she's not the girl next door - she's the girl across the aisle at math class. She did herself no favors and never presented herself as something she was not - there is a moment in SC where she is crying while sitting down in a school hall and Hughes shows us her legs and we realize that she think's she's plain when she's actually nymph-like. True, that's creepy in terms of Hughes' obsession with her. But it played off the idea of teenagers of that era having no objective sense of themselves in terms of attractiveness or anything else. And I don't think that Tuesday (gorgeous) or Winona (exquisite) or even Annette (too wholesome overall) could have ever managed something that transparent.

Molly Ringwald.

Molly by a mile.

Winona might have either been lucky or had better taste in picking projects, because she's done the best in terms of longevity even after that shoplifting scandal. After the late 80's, Molly never really did anything else that had the same sort of impact as those Hughes movies. She mostly popped up as a secretary or supportive mom.

Winone isn’t around much, unfortunately that talentless pumpkin head Christina Ricci is.

Winona was in Black Swan and Stranger Things, R6. She's doing alright, all things considered, and has aged beautifully.

Winona is/was a bit of a slut. She really got around.

Molly Ringwald was great in a TV movie about teen suicide called SURVIVING: A FAMILY IN CRISIS, which was released at the height of her fame/popularity. Quite a stellar cast, too: Zach Galligan, River Phoenix, Ellen Burstyn, Paul Sorvino, Len Cariou, Marsha Mason, Heather O'Rourke.

It's free to watch on YouTube.

Tuesday in George Axelrod's Lord Love a Duck (1966)

Are you people kidding me in this thread? Molly Ringwald is one of the worst actresses to have that insane degree of fame she did. Terrible actress, plain looking, and uncharismatic. Winona is a master thespian compared to her.

R11, but Ringwald was far more talented than the other options given at OP’s post.

No she wasn't. The singular performances in which she was adequate were Sixteen Candles and The Breakfast Club, and most of the big-name actresses in her age range could have easily played them just as well or even better. And she didn't ever fit in a film when she wasn't playing a teenage plain Jane self insert with a cunty attitude.

Actually, Anthony Michael Hall was far more natural and believable in both of the movies he did with Molly, his career going down the shitter is a bigger mystery.

None of those actors could touch Tuesday Weld for talent.

R9- Didn't she play that girl who got AIDS from the GAY bartender at Studio 54 in the early 1980's?

Christina Ricci isn't talentless. And she is good on her Yellowjackets.

R15, how does a woman get AIDS from a gay bartender???

Was she sharing needles with him???