Everything here is a potential spoiler so don't read any of it if you haven't watched it or want to figure it out yourself.
We were supposed wonder whether the whole thing is a classic bermuda triangle time travel movie, an eternal Sisyphian hell movie or a psychologal trauma movie. I considered all and decided its a little bit of all.
I believe Jesse crashes her Car at 8:17 on her way to the Triangle, causing Tommy's death (because of her impatience,cruelty etc towards her autistic son). The guilt deeply affects Jesse and she creates this alternate reality(Jesse is probably in a coma or in a catatonic state) which is a personal hell where she attempts to save her son but end up where she started every time,because she can't change the results of the events happened in reality.
She supports this memory with a bermuda triangle time travel story and Sisyphus' story to fill out the parts where it doesn't make sense. Jess lives in Florida(you can tell it's Florida from the Goodbye sign which can be seen on 00:04:11) which is one of 3 points of bermuda triangle so she should be familiar with it's stories.I'll explain why i have come to this conclusion. Also i'll point out some stuff that i think are important but i can't figure out why, hopefully you guys can help me out.
Before we begin, About the timeline:
First of all this is not a time travel movie so there are some stuff that doesn't make sense like some items being reset while others accumulate or the fact that it is impossible to enter this kind of loop in reality. These 2 problems can be explained by accepting this is actually the subconscious of Jess, which was triggered by the crash. Nevertheless from what i understand there are 3 different versions of Jess on Aeolus at all times.
One of them is our Jess(aka Pre-Masked Jess, becomes Masked Jess in future),
One of them is Masked Jess( the one who shoots everybody in the theater except Jess who will become Masked Jess in the future)
One of them is the Bloody face Jess(the one who kills Downey and Sally with a knife.)
One of them is the pre-Bloody face Jess(Jess who was in the same room with our Jess and Victor at the ballroom and runsaway after facing herself.Becomes bloody face Jess in future)
Only 3 of them are on the boat at the same time though. For example in the scene where our Jess watches pre-Bloody face Jess kill Bloody face Jess and dump her to water. Then a new version of our Jess arrives arrives a few minutes later. Still 3 Jess on board, this moment is actually has the same conditions with the 22nd minute of the movie where we see triangle passengers to board the Aelous for the first time. 01:05:57
Another case where all 3 Jess' are accounted for is where our Jess fights Masked Jess, at this time you can hear the 3rd Jess Running on the deck above. 00:38:38
Few minutes later masked Jess falls another one boards keeping the count at 3.
There is also a scene where Jess enters room 237 we see 3 Jess' on the screen. 00:30:19
About Sisyphus:
Basically this guy is sent to hell, not purgatory. What you can call Christian purgatory is called the underworld in Greek myths. Sisyphus is sent to Tartarus which is the place where souls are sent to suffer for their sins after they were judged and found guilty at the underworld. So it's good old hell.
Everybody uses Sisyphus example when talking about Tartarus so people just think about pushing rocks. Tartarus is what you can call a special kind of hell where you are sentenced to an eternal punishment in a place specially designed for you and your sin. A good example is Tantalus here's what wiki says:
"Tantalus who was also graciously invited to dine with the gods, felt he should repay them for their kindness and hospitality, but in his pride, decided to see if he could deceive the gods. Tantalus murdered and roasted his son Pelops as a feast for the gods. Demeter, one of the goddesses who preferred to walk with the mortals, graciously accepted the food, but was immediately repulsed when she bit into the left shoulder. The gods all became violently ill and immediately left for Mt. Olympus. As his punishment for such a heinous act, Tantalus was chained to a rock in the middle of a river in Tartarus with a berry bush hanging just out of reach above his head. Cursed with unquenchable thirst and unending hunger, Tantalus constantly tried to reach the water or food, but each time, the water and berries would recede out of his reach for eternity. It is from Tantalus's name and torment that we derive the English word "tantalise"."
Important events,objects...
Seagulls
Through out the movie there are numerous times where Jesse hears, looks at Seagulls or the camera follows seagulls. I believe seagulls here represents the freedom the main character cannot have. So we are constantly reminded that Jesse feels trapped all the time.
Also Jess hits and kills a seagull with her car 01:27:17 which symbolizes that she is responsible for loss of her freedom and it has something to do with the car, few moments later she crashes.
Dreams
There are overwhelming clues that the events happening on Triangle and Aeolus are not real.
1-First dialog of the movie: 00:00:50
Jesse: You're just having a bad dream, thats all it was. Bad dreams make you think you've seen things that you haven't.You know what i do when i have a bad dream ? I close my eyes and i think of something nice, like being here with you.
Basically i think this is what goes through Jess' mind after the crash, she convinces herself that what happened wasn't real and manufactures a reality where can save her son can be with him again.
2-Broken toy sailboat 00:02:04
Jess picks up a broken sailboat from the pool that has similar damage as the triangle after the storms hits.
It's possible Jess never went on the actual triangle but she just used this image subconsciously and made up rest of the memory.
3- Jess' house number is 237, thats the number of the room they go in Aeolus.
Another indication of subconscious images in the events.
4- Jess' sleeps and dreams at the triangle. Jess seems to be losing some of her memories after the sleep. She doesn't remember what will happen on the ship but she recognizes it. Also when she wakes up first thing she asks is 'Is Greg ok ?'
I believe she doesn't suffer from amnesia here but rather it's caused from being in a dream like state. You know the feeling when you wake up in the middle of the dream you know how it makes you feel, you know what it was about remotely but you don't remember any specifics.
5- Time is acting strange, all clocks in the ship and Jess' show 8:17 all the time, Jess is aware there is something wrong but nobody seems to dwell on it.
(8:17 is most likely the crash time and time stopped for Jesse)
Another case is when Jess returns to the ballroom all food are rotten as if weeks have passed. 00:33:50
6- Greg: You're in shock. Is it Tommy ? Is it guilt ? Do you feel guilyt is that what it is ? 00:29:36
Greg acts something like the guide or inner voice of Jess. Which is implied from the scene where Jess asks Greg 'Where do i aim ?' when Greg hands her the wheel.
7- Greg: Don't you see this is just on your mind. Ships have skipers but maybe in your wold right now they don't. 00:31:58
Stuff i don't get/can't connect with my main theory:
Cab driver: Cab driver isn't Hermes because in the story Hermes forces Sisyphus to return to the underworld against his will. Jess goes with him willingly.
When explaining Sisyphus myth Sally says 'He made a promise to death that he didn't keep' and when cab driver asks Sally if she's coming back she says 'I promise' 01:31:55 Which clearly points out to us that cab driver is death but if you look at the story this way Jess was sentenced to eternal torture because she didn't pay her cab fare(as someone else pointed out in these forums ). Which is ridiculous. Also in the original story Sisyphus doesn't promise his return to death but to the queen of the underworld Persephone instead.
My theory is Cab driver is Charon. Wiki says:
"In Greek mythology, Charon was the ferryman of Hades who carried souls of the newly deceased across the River Acheron that divided the world of the living from the world of the dead. A coin to pay Charon for passage, usually an obolus or danake, was sometimes placed in or on the mouth of a dead person. Some authors say that those who could not pay the fee, or those whose bodies were left unburied, had to wander the shores for one hundred years."
Charon is usually pictured as a old skinny man or even a bare skeleton wearing a robe which became the personification of death in the modern culture.
Another key point is that Jess Wakes up in the shore and appears to be dead.Just like in the article i quoted. But i can't make any sense to why this was included in the movie. Since it makes the Sisyphus reference unnecessary.
The gramophone room scene: 00:42:10
Jess looks at the mirror and checks the bruise on her left cheek, then she hears the noises coming from the triangle and goes out to check. But the camera doesn't follow Jess, it goes into the mirror and follows her reflection instead. When we enter the mirror with camera we see the triangle is on the right side of the Aeolus where it should be on left as we see on minute 22. The Jess boarding at this moment is the one which becomes bloody face Jess later so is this a reference to the myth that what we see in the mirror is an alternate evil version of our world and the evil jess comes out of the mirror dimension or something ? Doesn't makes sense or fits the movie in anyway.
Bloody face Jess and Jess' body after the crash:
They both have the same blood pattern on their face. Is this a reference that Jess sees herself to be evil because of the accident ? On the Aeolus, bloody face Jess is portrayed as a cold blooded killer.
I guess thats it for now, tell me what you think...