2016 Final Best Supporting Actor Predictions

Supporting Actor is probably the weakest category.  As usual there is one strong frontrunner (Mahershala Ali for Moonlight) that kind of overshadows the rest which don't seem as notable.  Hugh Grant will get a career nomination for Florence Foster Jenkins and Jeff Bridges will represent his ensemble for Hell or High Water.  But neither represents the strongest work of the year.  Dev Patel should get his first nomination for Lion, but he is a more vulnerable nominee than the other aforementioned three.

Which leaves a fifth slot that could go several ways, none of them all that strong of contenders.  Going with my gut with Michael Shannon representing the cast of Nocturnal Animals.  But if Manchester by the Sea becomes the favorite we could see Lucas Hedges, if Hell or High Water does incredibly we could see Ben Foster alongside Bridges, Aaron Taylor-Johnson may end up as the representative for Nocturnal Animals instead of Shannon.  But it could also be a less likely contender.  Moonlight, Fences and Silence all have strong male heavy ensembles.  This is the category with room for a surprise nominee this year.

Here are my predictions and analysis for Best Supporting Actor: 

PREDICTED NOMINEES
Mahershala Ali, Moonlight	Hugh Grant, Florence Foster Jenkins	Jeff Bridges, Hell or High Water	Dev Patel, Lion	Michael Shannon, Nocturnal Animals
The clear frontrunner who has been cleaning up every precursor, except the Globes.  Nobody is strong enough to beat him at this point without a SAG win.	This will be his career nomination.  Meryl Streep will carry him to the Oscars for the first-time.  But doesn’t seem strong enough for a win.	Bridges has been representing his ensemble on this surprisingly strong sleeper.  He won recently enough for a similar performance that this won’t get him a second Oscar, but he will get a nomination.	Missed out for Slumdog Millionaire, but this category is open enough for him to finally get a nomination.  He is not quite strong enough to be considered a lock, but has better chances than others.	One of the hardest working supporting players who got his second Oscar last year.  May be too soon for another, but he is the most likely representative of his ensemble.  Although missing out at the Globes (to Taylor-Johnson who won) makes his chances unsure.
THE RUNNER-UPS
Lucas Hedges, Manchester by the Sea	Ben Foster, Hell or High Water	Aaron Taylor-Johnson, Nocturnal Animals	Mykelti Williamson, Fences	Adam Driver, Silence
If Hedges is nominated, you can officially consider Manchester by the Sea as the Oscar frontrunner.  But he is an unknown name that hasn’t been up for many precursors.  This is a weak enough category where it could happen, but betting on not.	Hell or High Water has been doing amazing with precursors and Foster has received some mentions.  He has the flashiest role in the movie and could get in along with Bridges.  If Hell or High Water really resonates with voters then Foster could sneak in here.  He is bound to get a nomination eventually.	Taylor-Johnson not only was nominated for a Golden Globe, he won over Ali, Bridges and Patel.  He was also just nominated for a BAFTA, he may be stronger than expected.  But Globes can often fluke in this category and it is weak enough for a fluke precursor to happen.  Nocturnal Animals isn’t an incredibly strong contender, but Taylor-Johnson could still surprise.	Fences has an amazing ensemble, but only Denzel and Viola seem to be up for any awards.  Out of the four men, Mykelti is the best known name and has the most Oscar friendly role.  The four could cancel each other out.  Fences isn’t a strong enough contender to necessarily carry many surprise acting nominations.	Another ensemble with plenty of great actors that haven’t been in contention.  Driver’s career is getting to the right place for an Oscar nomination, but he isn’t strong enough yet.  Could cancel out votes with Liam Neeson, Issey Ogata and Tadanobu Asano.  None of whom haven’t received precursor notice.
THE LONG SHOTS
Andre Holland, Moonlight	Stephen McKinley Henderson, Fences	Aaron Eckhart, Sully	Peter Sarsgaard, Jackie	Alan Rickman, Eye in the Sky
Andre Holland and Trevante Rhodes are an important part of Moonlight’s success, along with the younger versions of Chiron and Kevin.  But Ali and Harris are the only members of the ensemble getting awards attention.  Holland has the edge on the rest with name recognition, but they should have appeared before now.	Last year, Mark Rylance, a stage veteran won in this category despite not having notable screen credits.  Henderson is similar, but should have been in the conversation before now.  Category is weak enough for surprises, but Fences doesn’t seem to be producing them.	Seemed likely earlier in the season when Sully opened great.  But the film has fallen out of serious awards contention and Eckhart will have to wait longer for his Oscar nomination.	Like Eckhart, Sarsgaard’s first nomination seemed possible earlier.  But Jackie is not up for much.  Natalie Portman will be getting a nomination, but she isn’t strong enough to bring other actors with her.	Oscars don’t always give a sentimental nomination, but it has happened.  Rickman’s final screen appearance was in a well-received film, albeit one that was released earlier and isn’t up for serious consideration.  Rickman unfortunately has not been nominated for any Oscars, but doubtful he will get his career nomination.

2016 Best Actress Final Predictions

This is an incredibly strong year for leading actresses.  There will be a lot of quality contenders left out.  While there are so many strong actresses there is no real clear frontrunner.  This could go several ways.  Have Emma Stone as the current frontrunner, especially if La La Land sweeps the night.  Amy Adams has had five previous nominations, she is definitely due.  But we should have seen her win more during the precursors for Arrival if it was her time.  Earlier it seemed like Natalie Portman would take it for Jackie, but that film has fallen out of the conversation.  Her Golden Globe loss was notable.  Isabelle Huppert could get a veteran vote for a challenging role in Elle, foreign language films can often do well here.  One of these four will win, Stone has the current edge as she is attach to a potential Best Picture frontrunner.  All are assured nominations.

That would leave the final slot going to Meryl Streep for Florence Foster Jenkins.  The film performed well and the Golden Globes proved how beloved the Oscar staple continues to be.  This won't earn her a fourth Oscar, but she is most likely going to have a nomination.  Although if there is a surprise, she is the one to go.

Here are my predictions and analysis for Best Actress:

PREDICTED NOMINEES
Emma Stone, La La Land	Amy Adams, Arrival	Natalie Portman, Jackie	Isabelle Huppert, Elle	Meryl Streep, Florence Foster Jenkins
No frontrunner for this category.  You could make the case for four actresses winning.  Right now Emma Stone seems most likely.  Well-liked, young talent with a previous nomination who is starring in one of the Best Picture frontrunners.  Not a strong lock, but until a SAG winner shakes it up, she seems most likely.	Amy Adams has lost five times before.  She is definitely due and she has had a good year.  Arrival did great business and she also played the Oscar game with Nocturnal Animals.  However she should have been winning more in the precursors if she was going to have her career win.	Seemed like the frontrunner earlier, but the film has almost completely fallen out of the awards conversation.  She should get a nomination, but it doesn’t seem strong enough for her to second win.  Her career hasn’t been strong enough in recent years and this isn’t a strong enough film to give a fairly young actress a second leading Oscar win.	The Golden Globe winner that many seemed to think wouldn’t make the final cut. Huppert is a veteran actress in a powerful, controversial role.  Her performance has the edge her competition lacks.  This is also the category where foreign language performances can do well.  She may end up with the Oscar in the end.	Her Golden Globe speech clinched her Oscar nomination.  Factor in Hugh Grant’s likely nomination and there is enough strength for Streep.  She has been nominated pretty consistently in recent years over strong competition (August: Osage County, Into the Woods).  She will continue her streak as being an Oscar mainstay.
THE RUNNER-UPS
Annette Bening, 20th Century Women	Emily Blunt, The Girl on the Train	Taraji P. Henson, Hidden Figures	Ruth Negga, Loving	Jessica Chastain, Miss Sloane
Bening is one that pundits seem to overestimate.  She is well respected, but is inconsistent when it comes to the Oscars.  Her film isn’t strong enough, but she has remained in the conversation just enough to stay a runner-up.	Not really an Oscar film, but Blunt received a surprise SAG and BAFTA nomination for the role.  Rosamund Pike was nominated for a similar pulpy role a few years ago.  Blunt is on her way to an Oscar nomination, especially after missing for Sicario last year.  It isn’t a sure thing, but she is still in the running.	Previous Oscar nominee with a popular TV series.  This film should be fresh in voters’ minds and is doing great at the box-office.  It isn’t the showiest Oscar bait, but Henson is strong enough for continued consideration.	Negga is falling out of contention with stronger competition outperforming her.  She is not a name yet, while the others in consideration are a bit more established.  Loving needs some Best Picture love for her to make the cut, but it seems less and less likely.	Chastain missed her Oscar a few years ago and will definitely earn her way back.  Miss Sloane did well enough, but she is a fairly weak contender at this stage of the race.  She will have to wait for another year.
THE LONG SHOTS
Rebecca Hall, Christine	Kate Beckinsale, Love & Friendship	Amy Adams, Nocturnal Animals	Sally Field, Hello, My Name is Doris	Marion Cotillard, Allied
Hall has done a lot of great work, but has never been up for Oscar consideration.  This is her edgiest performance, but the film seems too small.	Surprise arthouse hit from earlier in the year and the best chance Beckinsale has ever had at an Oscar nomination.   Not strong enough though.	Bolstering Adams Oscar credentials is another baity film.  Nocturnal Animals is not a sure thing, but some voting bodies have responded to it.  Not going to overshadow Arrival, but definitely worth mentioning.	Veteran actress with a great late in life lead role.  This was released too early for Field to make the cut.	Cotillard is always interesting in Oscar season.  She almost always has one role in early contention, but they usually fall off by the time the Oscar nominations are announced.  This year is no different.

2016 Final Best Actor Predictions

Best actor is going to go to Casey Affleck for Manchester by the Sea.  He is a big part of why his film has a chance at winning Best Picture.  Denzel Washington in Fences is the only actor this year that could possibly surprise with a win.  But Affleck has been too consistent in the precursors, and Washington already has two Oscars.

The rest of the nominees are pretty set, but won't win.  The success of La La Land will finally land Ryan Gosling his second nomination.  Viggo Mortensen has been consistently nominated for Captain Fantastic.  Hacksaw Ridge should earn Andrew Garfield his first nomination.  Most of the other leading male performances have fallen out of the race or lack the strength to challenge these five.

Here are my predictions and analysis for Best Actor:

PREDICTED NOMINEES
Casey Affleck, Manchester by the Sea	Denzel Washington, Fences	Ryan Gosling, La La Land	Viggo Mortensen, Captain Fantastic	Andrew Garfield, Hacksaw Ridge
Frontrunner who has been cleaning up in the precursors.  Affleck has another nomination to his credit.  His main obstacle are his personal controversies, but that has been mainly ignored.  Guessing that it won’t factor for voters.	A lock for a nomination, but doesn’t seem strong enough for his third Oscar.  Going to need a SAG win to seriously threaten Affleck, but there isn’t anybody else who could at this point.	Always loved by critics and the internet, but Gosling only has one Oscar nomination to his name.  Leading a frontrunner picture will secure him a nomination.  Although it isn’t deep enough to challenge Affleck and Washington.	Small film role from earlier in the year that has had some staying power in the precursors.  A SAG ensemble nomination for Captain Fantastic shows the strength in Viggo as a contender.  He will get a nomination, but isn’t up to win.	Garfield has been playing the Oscar game well after Amazing Spider-Man.  He missed before for Social Network.  In the past two years he has done 99 Homes, Silence and this.  He is serious about getting an Oscar nomination, and Hacksaw Ridge is just strong enough to get him one.
THE RUNNER-UPS
Tom Hanks, Sully	Joel Edgerton, Loving	Michael Keaton, The Founder	Jake Gyllenhaal, Nocturnal Animals	Adam Driver, Paterson
Hanks has missed out the past few times he’s played the Oscar Game (Captain Phillips, Bridge of Spies).  Sully won’t carry him, but he is the only one that could really surprise.  He is overdue for Oscar love and Sully did well enough to justify a nomination.	Edgerton has been around Oscar films before, but hasn’t been in serious contention.  Loving isn’t strong in any categories, but he is just as strong as anyone who could crack the top five.  Edgerton is right on the border of being due for an Oscar and just being a serviceable leading man.  Lacks the reputation of a Tom Hardy or Gosling to carry him.	Keaton has been doing an Oscar film each year for the past several years.  His lost for his comeback in Birdman and didn’t make the cut with Spotlight last year.  The Founder is much weaker than those two films, it is really only considered in this one category.  Keaton seems like he will have to wait a bit longer.	Gyllenhaal has been doing really strong work the past few years, but Oscar hasn’t bitten.  Nocturnal Animals is enough of a question mark where the Oscars could fall for it where other voting bodies haven’t.  It is most likely that Gyllenhaal will keep waiting for that second nomination.	Driver is making great career choices.  Paterson has the right critical response, but is just too small for him to get in on this category.  A few more of these roles and he will be nominated in the next few years though.
THE LONG SHOTS
Andrew Garfield, Silence	Chris Pine, Hell or High Water	Warren Beatty, Rules Don’t Apply	Don Cheadle, Miles Ahead	Miles Teller, Bleed for This
Earlier in the year Garfield seemed more likely for this than Hacksaw Ridge, but Silence is not a strong contender in any category.  Garfield will get the nomination for Hacksaw, but this bolsters his Oscar credentials this year.	Hell or High Water is a strong contender, but Pine has not been in the conversation at all.  It won’t be strong enough to earn him a nomination, but it is the closest Pine has come to an Oscar film.	Beatty’s return was incredibly uneventful.  But his name still means something and Oscars have honored older actors in lesser performances before (Duvall in the Judge).  But Rules Don’t Apply will most likely be shut out.	Early, small contender.  Nowhere near strong enough.  But it has just as much chance as any of these other long shots at this point.	There have been a lot of boxing films in the past few years and Teller has done the physical transformation that voters respond to.  But if Gyllenhaal and Michael B. Jordan have been ignored for bigger boxing movies, Teller won’t make it in.  He is too divisive of a figure and nobody is really rooting for him as an up and comer for him to make the cut.

2016 Final Best Director Predictions

It is a race between Barry Jenkins for Moonlight and Damien Chazelle for La La Land.  As we've seen in three of the last four Oscars, a split between Best Director and Best Picture is possible (Argo/Ang Lee, 12 Years a Slave/Alfonso Cuaron, Spotlight, Alejandro Inarritu).  Either Jenkins or Chazelle will win, even if Manchester by the Sea ends up taking picture.  Going with my gut right now and predicting Barry Jenkins.

Manchester by the Sea is a strong enough contender to secure a slot for Kenneth Lonergan.  His film is more about the writing and acting than direction.  As he is primarily a writer, he needs to amass a larger body of film work or  develop distinct direction before he can win in this category.  Denis Villenevue is set for a nomination for Arrival.  He has been working a lot on quality projects, with the film's financial success he will receive a deserved first nomination.  The final slot will likely go to Mel Gibson for Hacksaw Ridge, who has been present in precursors and has a strong-enough film.  There is some room for surprises, this is a category where that has happened recently.

Here are my predictions and analysis for the Best Director race:

PREDICTED NOMINEES
Barry Jenkins, Moonlight	Damien Chazelle, La La Land	Kenneth Lonergan, Manchester by the Sea	Denis Villeneuve, Arrival	Mel Gibson, Hacksaw Ridge
This award could go several ways.  As of right now I am predicting Barry Jenkins to win.  This is the strong new director that the Oscars will support.  A lock for a nomination for sure, but the win is not certain.  Going with my gut right now.	Seems neck and neck with Jenkins, Globes gave him a slight edge.  Chazelle has a previous Oscar nominated film which helps.  His film will get the nostalgic vote, unsure how many that will carry to wins.	Lonergan is a writer who has never been up for an Oscar as a director before.  The strength of his film will get him a nomination, but Manchester needs to take the frontrunner place for Lonergan be considered to win.	Villeneuve has been on his way to an Oscar and he has a much talked about critical and commercial hit this year that is assured an Best Picture nomination.  Arrival isn’t strong enough for Villeneuve to win, but he will get his first nomination.	Gibson has been nominated in a lot of precursors.  The fact that Hacksaw Ridge is up for Best Picture and Best Actor shows that Gibson may be done with his exile.  Also worth noting that other directors will vote for this award, not actors.  Controversial directors have been nominated and won before.
THE RUNNER-UPS
Denzel Washington, Fences	David Mackenzie, Hell or High Water	Martin Scorsese, Silence	Jeff Nichols, Loving	Clint Eastwood, Sully
Did a great job making Fences cinematic while still maintaining its theatrical aspects.  Washington directed a great ensemble, but he hasn’t been up for many precursors.  Directors of play adaptations aren’t always up for Oscars.  Director-actors haven’t been successful lately (Affleck couldn’t secure a nomination for Argo).	While not a frontrunner, this film is going to be up for several Oscars.  While the director hasn’t been seen in many precursors, this category can have surprises.  Benh Zeitlin and Michael Haeneke making it in 2012, Bennett Miller getting nominated while his film didn’t.  Mackenzie could ride the strength of Hell or High Water.	Scorsese is one of those directors who can get recognized for lesser work.  Silence has not been greatly received and is not up for many Oscars.  But the director’s respect for Scorsese and his passion for this project could come into play.	Nichols will get a nomination one of these days.  He is consistently making good films, but the Oscars have yet to truly embrace one.  If Loving gets a Best Picture nomination, Nichols could follow.	Eastwood can just be a sign of quality for some voters.  Sully did well enough financially that it isn’t out of the question entirely; he wasn’t in the conversation much before American Sniper’s nomination either.  But Eastwood has been divisive this year and his film lacks the passion of Sniper.
THE LONG SHOTS
Garth Davis, Lion	Theodore Melfi, Hidden Figures	Tom Ford, Nocturnal Animals	Mike Mills, 20th Century Women	Jon Favreau, The Jungle Book
Lion will most likely get a picture nomination, so Davis could get in with little precursor love (ala Zeitlin).  Not likely though.	Hidden Figures is a star vehicle, not a director’s vehicle.  It isn’t popular enough to reward a serviceable director.	Some voting bodies are responding to Nocturnal Animals.  Ford got a Globe nomination over better competition.  But it will be a real long shot at this point.	Mills has his fans and supporters, but the film is a real long shot in most categories.  He is not a serious threat.	Some pundits still bring up The Jungle Book as a contender.  I suppose that if Ang Lee could win for Life of Pi then it isn’t inconceivable.  Favreau has worked enough to deserve an Oscar moment.  But this mainstream fare won’t be it.

2016 Final Best Picture Predictions

Best Picture is a three way race right now.  Moonlight, La La Land and Manchester by the Sea are the only ones with a chance to win.  Moonlight is the progressive vote, the scrappy new voice that represents the current reality of race and sexuality.  La La Land is the nostalgic vote, a film about filmmaking and old fashioned idealism.  Manchester by the Sea is not as strong as the other two, but it will be an emotional vote.  Audiences are connecting with its themes about grief and it has a strong impact.  Manchester has the potential to sweep in if there is a divide between Moonlight and La La Land.

With the Academy's preferential voting system it doesn't seem like we will never see ten Best Picture nominees again.  There will be 8-9 nominees, I am going to predict 9 nominations because that is the usual number.  Hell or High Water and Arrival are sure nominees, but they don't have a chance at winning.  Fences and Hacksaw Ridge aren't as strong, but expect them to be among the 9 as well.  The final two will most likely be Lion and Hidden Figures, although if anything upsets those two will be out.

Here are my predictions and analysis for the Best Picture race:

TOP PREDICTED FIVE NOMINEES
Moonlight	La La Land	Manchester by the Sea	Hell or High Water	Arrival
Moonlight gets the progressive vote.  After years of lacking diversity, this is a film that acknowledges race and sexuality in a powerful way.  Moonlight may be too small but that hasn’t stopped Hurt Locker and others from winning.  It is also not overexposed in the precursors; films that are preordained to win early on often fizzle out.  Moonlight is still being discovered and discussed.	La La Land gets the nostalgic vote.  It is comfortable and idealistic.  It is about Hollywood and voters can really respond to that (The Artist, Argo).  Musical films can feel really fresh after the genre not being popular for a while.  La La Land has enough serious contenders in directing, acting, writing and technical categories to be taken seriously.  But it missed out a SAG ensemble nomination and may be getting too many precursors, votes may look elsewhere after this being hyped for so long.	Manchester by the Sea gets the sentimental, emotional vote.  It is about grief, voters really respond to that.  Add in a frontrunner for Best Actor and Best Original Screenplay, this has a chance at winning.  However precursor support isn’t as heavy and Affleck’s controversies could still weigh it down.  It isn’t making the same impact as Moonlight or La La Land.  But it could benefit from vote splits between the two.  Manchester needs just enough voters to rank it Number One.  It may make a big enough emotional impact for that to happen.	This is a small summer limited release that became a sleeper and good word of mouth has grown.  It has a great ensemble and many are viewing this as a good look at Trump’s America.  This film is sympathetic to the working class American, which is an important issue.  It won’t have the support to win, but it is assured its nomination and will be up for several important categories.	This will be nominated for sure.  A critical success that had people talking and earned great box-office.  Amy Adams is a sign of quality and Denis Villeneuve has been working towards a Best Picture nominee.  This will be up for screenplay and important technical nominations.  It may not win much, but it will receive a lot of nods.
NEXT FOUR PREDICTED NOMINEES/RUNNER-UP FILM
Fences	Hacksaw Ridge	Lion	Hidden Figures	Sully
Powerful drama incredibly adapted from an important play.  Plays don’t always translate to Oscar nominations but with the two strong lead performances and screenplay you can count on this nomination.	This earlier release has stayed in the conversation and done consistently well among precursors.  It is strong enough to get Gibson a directing nomination and Garfield his first acting nod.	Not a strong contender, but it has outlasted a lot of competition.  Expect it to be among the nominees.	If the Oscars make it to 9 films, Hidden Figures will be among them.  Its strong box-office shows real interest in this subject.  Octavia’s guaranteed nomination doesn’t hurt.  Not incredibly strong and might be left out if only 8 films are nominated.	Have Sully as the first alternate.  Doubtful ten films will ever be nominated again (Oscar voting is so messed up).  Sully did good business, had decent reviews and is associated with Eastwood and Hanks.  Good enough to make it in.
THE LONG SHOTS
Silence	Loving	Florence Foster Jenkins	Nocturnal Animals	Deadpool
Respect for Scorsese is what will get this in.  But looking at precursor and the film’s overall potential nominations it is not looking great.	Loving just hasn’t received the precursor notice required.  More likely than other films, but it is pretty much out of the race.	Streep may be able to carry this film to a nomination.  It did good box-office and has a supporting actor nomination and potential writing nomination.  Just good enough to be a safe vote (ala Extremely Loud).	Some voting bodies are really responding to this, others are not.  Think this is out of the race for the most part.  Especially since Amy Adams nomination will be for Arrival.  Still strong enough to surprise.	Yes, this got a PGA nomination.  They have nominated other genre fare (Ex Machina) and films that don’t make it to the Oscars (Sicario).  Deadpool won’t make it in, but it has surprised enough that I have to mention it.

Figuring Out Disney's Future Releases

Disney has a bunch of open dates on their upcoming schedule.  They released a list of the live-action fairytales they currently had in development.  This helps to decipher what might go into those dates.

Jungle Book 2 would go into the April 2018 slot.  That is two years away and Favreau and the writer Justin Marks are already on board to continue the story.  The Jungle Book left it open for more of Kipling's jungle stories.  Releasing it around in April again makes a lot of sense.

I would expect Nutcracker and the Four Realms to be released on November of 2018.  The Nutcracker Suite is so associated with Christmas that a November release date makes sense.  This is one of the few projects to have a director not associated with several other projects.  Lasse Hallstrom can work on this soon.

There is a Disneytoon Movie schedule on April 2019.  Disneytoon is not as active as it once was with Disney sequels.  It has really only created Tinker Bell and Planes movies recently.  I think Disney wants their animation studio to keep making original movies that can create their own brands.  This gives Frozen 2 a theatrical release without having to slow down their main studio.

I will put A Wrinkle in Time in the November 2019 slot.  It is going to be directed by Ava DuVernay, but she will be busy with Intelligent Life in 2017.  Wrinkle will need two years of her time and around winter is a good release date for it.

The sequel to Mary Poppins will be released the following month, December 2019.  They have Rob Marshall, Lin-Manuel Miranda and Emily Blunt attached and you need to release this during Oscar season.  Expect a firm announcement when Moana is released.

2018 has two live-action films with release dates.  These are not designated as fairytales so they must be something different.  Jungle Cruise might qualify and this would have to be a summer movie.  Expect the Dwayne Johnson vehicle to be released on August 2018.

That means that December 2018 must be Colin Trevorrow's Star Wars Episode IX.  I wouldn't expect it to be released the same year as a Han Solo anthology film.  Episode IX had previously been dated for December 2019, but there is a Disney fairytale there right now.  Disney must want to release two Star Wars films in one year.  Not sure if that is the best idea, but there must be some reasoning behind it.

So that leaves July 2017 with one more Disney live-action fairytale release date.  The only remaining films I don't have slotted are Maleficent 2, Tim Burton's Dumbo, Tink starring Reese Witherspoon
 and Cruella.  I am going with Cruella, it doesn't seem like a summer film but Dumbo would take more than a year of production and Maleficent will take longer to schedule.  It is too close to Pan for Tink and Emma Stone is a better star to attach yourself to than Reese Witherspoon at this point.  Cruella will have less special effects and it has been trending this week.  So expect some sort of 101 Dalmatians prequel next summer.

Other release dates are for Pixar and Disney Animation in 2020.  I expect those to be original films.  Some may be projects we have heard about (Disney may release their Galactic, teen space race film).  But for the Marvel films that year I would guess Guardians vol. 3 for May 2020 and Doctor Strange 2 for November 2020.  Black Panther might need a sequel too, Captain Marvel can wait a year.  Inhumans might go in July, unless Marvel Studios has given up on that project.  There is always a chance Marvel will get Fantastic Four by then, but I will have to wait to find out for sure.

So the final schedule will probably look like:
July 2017- Cruella
April 2018- Jungle Book 2
August 2018- Jungle Cruise
November 2018- Nutcracker and the Four Realms
December 2018- Star Wars Episode IX
April 2019- Frozen 2
November 2019- A Wrinkle in Time
December 2019- Mary Poppins II
May 2020- Guardians of the Galaxy vol. 3
July 2020- Inhumans
November 2020- Doctor Strange 2