Winona Ryder or Jennifer Connelly?

Looks: I used to have a crush on them both but I say Winona.

Acting: Ryder has showed more range as an actress and has impressed me more.

Persona: Well, Winona again because in interviews, Connelly can be really boring.

Both actresses deserve to be in better films though. At least Winona has "Stranger Things".

I don't think Ryder is Huppert either.  I also think the type of movies they do is different, Ryder often gets thought of as less serious and fairly vanilla by some people.  Personally though, I don't really think like that.  And I certainly don't think Connelly's inherent intensity gives her more brownie points, or is there something that great about it.

I disagree about Connelly's best easily beating Ryder's best.  I find Con pretty one-note even at her best, that emo look she has transpires onto her work, and that's the main note I see.  I'm not a hater or anything, but I'm just leveling the field.  I appreciate your explanatory effort very much.
 
Let's say I do agree with you that Ryder isn't all that, i still think one thing she has to her credit is volume of work.  There's like 7-8 performances she's done I think is at the level of at least an Oscar nomination.  So taking that into consideration is where my opinion largely comes from.  And tbh, I don't feel she's developed either - or was that ever her trajectory.  She's always been in very big hits at the time though.  But she also did lose her charm with the times.

Connelly for all. The results so far are sickening.

Connelly may be the more natural performer, but for me, there is nothing interesting or exciting about her. Ryder would certainly have benefited from some classical training (she is legitimately awful in 'The Crucible'...), but she is absolutely the more watchable and charismatic of the two.

Yup , Winona is more exciting to watch to watch for sure.

Oh honey, I love Noni! She taught me everything I need to know about shopping...

Well, for talent, I have to put aside all nostalgia, and the fact that I grew up watching Winona Ryder in so many films that are close to my heart. Jennifer Connelly is just the better actress to me, so she wins on that. I think both are extremely beautiful, but Connelly for looks. Persona? Well, I guess Ryder has a more defined screen persona because of Heathers and Lydia from Beetlejuice, so she'd be the more obvious choice for that. I'm not someone who complains about Connelly being too serious though.

Jennifer
Winona
Winona

So, Winona

I shouldn't really answer as a giant fanboy of one, but what the hell.

Persona - JenCon is obviously not quite as wet for death as her on screen persona so often suggests given she married Paul Bettany, but Winona is/was an icon.

Talent - I mean I could go either way on it, but after her Oscar JenCon turned into one of the most boringly samey actresses around with barely a trace of light in sight. Winona has had some pretty gigantic off days, but the variety of her on days is epic.

Looks - Gorgeous as Winona was she can't really compete with a young JenCon. As Jen wasted away to the bone I'd say Winona outlasted her.

Winona's looks have definitely held on longer, save for the seriously disconcerting crazy-eyes. She has/(had) one of those faces that looked plain in one instance but pristinely beautiful in another. In that regard she's reminiscent of Olivia de Havilland.

I actually agree with pretty much all of this. 

Winona's off days are AWFUL, but because her on days are (were?) more varied and interesting, i'd probably pick her. She has nothing on her CV quite on the level of "Requiem" or "House of Sand and Fog", but looking at the rest of Connelly's body of work (outside "Labyrinth" which stands out as a fun film at least) I could honestly fall asleep. She is obviously talented, but dreadfully unexciting as a performer. Ryer is not 'obviously' talented, but she switches it up a lot more and actually does interesting projects. And sometimes she can be quite good in them too. 

Sorry honey I don't really understand the bolded. Might be my English. :? Is this a thing people say about actresses in general? 

But no, I can't say I really think Ryder displays an obvious talent, technique or craft on screen. She is not an Isabelle Huppert or Samantha Morton, and she's not very consistent... what she DOES possess is a great inherent screen presence, and a penchant for quirky and inventive characters. She definitely has given a couple of great performances (I happen to love her work in Reality Bites, for example). Regarding the 'obvious' comment, i'm not saying she's untalented, i'm just proposing that there are actress-specific qualities (consistency from role to role, effortlessness on screen, ease in transforming physical traits, strong use of the voice) that aren't quite there for her, or as readily available in her work when you take a first look at her performances.

Perhaps that is part of the appeal for some people.