Where else could one post a quiz such as this?

[Mister Tee]

I loved Frances Conroy on Six Feet Under, but I'm embarrassed to say I had zero recollection she was in ether The Aviator or Joker. (And I barely recognized her in Power of the Dog.)

Did anyone highlight, back in 2014, that Alec Baldwin had two years in a row played the husband of the best actress winner? You'd think it's something we would have noted, but I don't recall it coming up.

[Big Magilla]

I did relate Knight to Hunt in As Good as It Gets but dismissed the idea because I thought you were looking for a more specific family relationship

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[Uri]

So, here’s the full answer.

As FilmFan indeed suggested – this is about actors who played onscreen family members of characters whose portrayals won the Oscars – twice.
As far as I know, Conroy is the only performer to have played a parent of an Oscar winning “offspring” more than once – Katharine Hepburn Sr. in The Aviator and the Joker’s mother - a feat that might be increased even more this year.

Then there are those who had two Oscar winning onscreen parents. Colman played daughters to Streep* in The Iron Lady and Hopkins in The Father, both Fonda’s parents in On Golden Pond won, as did Henry’s in Kramer vs. Kramer. Al Pacino (and James Caan, John Cazale and Talia Shire) played Don Corleone’s kids in The Godfather saga, a role for which both Brando and De Niro won.

And while Knight had only one Oscar winning onscreen parent – Ed Begley in The Sweet Bird of Youth, she did go on to have an onscreen offspring – Hellen Hunt in As Good as IT Gets – who won too.

And yes, Jones played spouse to both Sissy Spacek and Jessica Lange in their Oscar winning roles, while Baldwin did the same (consecutively) with Cate Blanchett and Julianne Moore.

* Playing Streep’s onscreen child (as opposed to being a real life one, it seems) is a good omen for future Oscar winners – it worked for Leonardo Dicaprio, Rene Zellweger and Colman.

Uri, do these things just come to you, or do you spend hours and hours researching them?

It’s a combination of both. Once I spot a “pattern” intuitively – when Phoenix won I immediately thought of the Conroy connection, and last year, when Hopkins won I thought about Colman and Streep – and then I search for more.

[Big Magilla]

And what, pray tell, does Shirley Knight have to do with any of them?

[danfrank]

Ah. Frances Conroy has played many mothers, and usually ones that are not very warm or nurturing. I once saw her in the audience of a Broadway theatre where her former TV daughter, Lauren Ambrose, was performing. Evidence that she’s more nurturing in real life. Good actress.

Uri, do these things just come to you, or do you spend hours and hours researching them?

[FilmFan720]

Since no one else has posted the answer, I'll go ahead and say that for the first question, all of them won Oscars for movies in which Frances Conroy played their mother: The Aviator, Joker, and maybe The Power of the Dog.

I did have to rely on looking through the Wikipedia cast lists of those movies to deduce the answer, I will admit.

[Uri]

I had to do some Wikipediaing, but I believe that the first one would be true if EITHER Benedict Cumberbatch or Jesse Plemons wins this year.

Spot on - and I haven't thought about Plemons myself.

[FilmFan720]

I was thinking that if Cumberbatch wins, he would be an Oscar winner who is in the same film where the actor who played his sibling is also nominated, as was Cate Blanchett—with Sally Hawkins—in Blue Jasmine. However, this doesn’t seem to apply to Joaquin Phoenix, unless he just needs to be an Oscar winner who has been in some film where his sibling character was nominated. And if FilmFan’s clue applies, maybe all three of these actors would need to have been in multiple films where the actor who played their sibling was nominated.

I had to do some Wikipediaing, but I believe that the first one would be true if EITHER Benedict Cumberbatch or Jesse Plemons wins this year.

It also has to do with a familial relationship, but it doesn't matter if they were nominated or not.

I won't spoil it yet.

[danfrank]

I was thinking that if Cumberbatch wins, he would be an Oscar winner who is in the same film where the actor who played his sibling is also nominated, as was Cate Blanchett—with Sally Hawkins—in Blue Jasmine. However, this doesn’t seem to apply to Joaquin Phoenix, unless he just needs to be an Oscar winner who has been in some film where his sibling character was nominated. And if FilmFan’s clue applies, maybe all three of these actors would need to have been in multiple films where the actor who played their sibling was nominated.

[Uri]

What do Cate Blanchet, Joaquim Phoenix and, potentially, Benedict Cumberbatch have in common?

If I'm remembering Gladiator correctly (Connie Nielsen was Phoenix's sister, yes?), each was nominated for playing characters who lived with siblings. But that would apply to, minimally, Pacino and Vivien Leigh ('51) as well, so there must be more to it.

FilmFan offers the key.

And while all the part of this quiz have the same principal, the first part is done the other way round.

[Mister Tee]

What do Cate Blanchet, Joaquim Phoenix and, potentially, Benedict Cumberbatch have in common?

If I'm remembering Gladiator correctly (Connie Nielsen was Phoenix's sister, yes?), each was nominated for playing characters who lived with siblings. But that would apply to, minimally, Pacino and Vivien Leigh ('51) as well, so there must be more to it.

[Uri]

And on similar grounds – what distinction is shared by Tommy Lee Jones and Alec Baldwin (and only them, I think)?

OK, since Magilla's thoughts have me thinking in a familial direction with regard to lead winners -- both played husbands of best actress winners, but they weren't nominated themselves (even though they have been Oscar-nominated on other occasions). I haven't had time to run through the full list of best actress winners to see if this makes them distinct, but am in in the rough ballpark?

ON EDIT: Nah; even just recalling the last decade, Ryan Gosling would fit the description. Just tell me if this is a direction worth pursuing.

You are on the right track. But as you said - from Robert Montgomery in The Divorcee to James Cromwell in The Queen - there are so many of them. Why these two?

And while I was typing FilmFan came to the rescue.

[FilmFan720]

And on similar grounds – what distinction is shared by Tommy Lee Jones and Alec Baldwin (and only them, I think)?

OK, since Magilla's thoughts have me thinking in a familial direction with regard to lead winners -- both played husbands of best actress winners, but they weren't nominated themselves (even though they have been Oscar-nominated on other occasions). I haven't had time to run through the full list of best actress winners to see if this makes them distinct, but am in in the rough ballpark?

ON EDIT: Nah; even just recalling the last decade, Ryan Gosling would fit the description. Just tell me if this is a direction worth pursuing.

You are on the right track, Tee, but I think the catch is that they each did it twice.

[Mister Tee]

And on similar grounds – what distinction is shared by Tommy Lee Jones and Alec Baldwin (and only them, I think)?

OK, since Magilla's thoughts have me thinking in a familial direction with regard to lead winners -- both played husbands of best actress winners, but they weren't nominated themselves (even though they have been Oscar-nominated on other occasions). I haven't had time to run through the full list of best actress winners to see if this makes them distinct, but am in in the rough ballpark?

ON EDIT: Nah; even just recalling the last decade, Ryan Gosling would fit the description. Just tell me if this is a direction worth pursuing.

[Uri]

Greg already indicated Blanchett, Phoenix, and potentially Cumberbatch won for playing mentally distressed or disturbed characters.

Shirley Knight's first nomination was for playing opposite Lee Kinsolving as a mentally disturbed young man in The Dark at the Top of the Stairs.

No - it's not about playing mentally challenged characters - a case can be made about so many more characters anyway - the connection is very particular.

As I mentioned before - you're on something with that direction.