PHASE I
Iron Man
This is the first film and assumes as much. It very gradually introduces the audience to a superhero character before dropping the bomb of that it's only the beginning of a larger universe.
The Incredible Hulk
This film is stylistically similar to Iron Man and expands on the "larger universe" that Iron Man promised. We get our first character with actual powers.
Iron Man 2
This film escalates the universe and begins really putting pieces in place for The Avengers. The post credit scene sets up Thor.
One Shot: A Funny Happened on the Way to Thor's Hammer (on the Captain America Blu Ray)
This is an optional little interlude that expands on Agent Coulson on his way to the events of Thor.
Thor
Expands the cosmic side of universe and gives the biggest glimpse into SHIELD. It further sets up The Avengers by introducing its villain and the terrasect.
One Shot: The Consultant (on the Thor Blu Ray)
Functions as an epilogue to Thor and explains the closing scene from Hulk and precisely when those events took place.
Captain America: The First Avenger
Though chronologically the first of the series, it relies on Thor to make sense. The bookend scenes also take place almost immediately before The Avengers.
The Avengers
An act one finale to the events to date. This is the climax to stories from all five previous films and sets up the future of the series.
One Shot: Item 47 (on The Avengers Blu Ray)
This is an optional epilogue to the Avengers that mostly functions as a lead-in to Agents of SHIELD
PHASE II
TV Series: Agent Carter Season 1: Now is Not the End - Valediction
Although it came out in the middle of Agents of SHIELD's second season, it functions much better as a prologue for Phase 2. Several things in it either tie back to Phase 1 or set up things that will be paid off in the Phase 2 films.
One Shot: Agent Carter (on the Iron Man 3 Blu Ray)
This short film functions as a quasi-finale to the series, but its optional. It was made before the series and the differences are really apparent.
Iron Man 3
This is mostly a stand alone film. I would almost advise skipping it, but the story feeds into Agents of SHIELD.
Agents of SHIELD: Pilot - The Hub
Establishes the series and characters. This show plays the long game of slowly putting pieces in place before the payoff. Most of this batch is just setup, but every episode must be watched.
One Shot: All Hail the King (On Thor: The Dark World Blu Ray)
This is an optional follow up to Iron Man 3. I put it here because it comes with the Thor: The Dark World Blu Ray and thus reduces changing discs.
Thor: The Dark World
This picks up from the events of The Avengers and sets up Guardians of the Galaxy.
Agents of SHIELD: The Well - Repairs
The Well picks up from the events of The Dark World and Repairs is the last stand alone episode of the series before things start picking up.
Guardians of the Galaxy
This came out after The Winter Soldier, but it can easily be watched anytime between The Dark World and Age of Ultron. I put it here because the payoff from The Dark World is more immediate and it doesn't interrupt any stories from Agents of SHIELD.
Agents of SHIELD: The Bridge - End of the Beginning
This sequence of episodes feeds into The Winter Soldier. The viewing order gets a little hairy here, because there is a big crossover of simultaneous events, but End of the Beginning does not give away any surprises from The Winter Soldier, while its followup, Turn, Turn, Turn, assumes you have seen the film.
Captain America: The Winter Soldier
This ties into the Agents of SHIELD story and sets up Age of Ultron.
Agents of SHIELD: Turn, Turn, Turn - End of the Beginning
These episodes wrap up the fallout from The Winter Soldier events.
Daredevil Season 1: Into the Ring - Daredevil
There is a three month gap between seasons of Agents of SHIELD and this series fits well in there. It only references The Avengers, so it doesn't affect Agents of SHIELD or any of the following films. Please note that this series is much more mature content than any of the others. It's not recommended for kids.
Agents of SHIELD Season 2: Shadows - The Dirty Half Dozen
Starts a new serialized story that it follows for the entire season. Fortunately, unlike The Winter Soldier, Age of Ultron fits seamless between the episodes The Dirty Half Dozen and Scars.
Avengers: Age of Ultron
Functions as an Act 2 climax to the stories from The Dark World, The Winter Soldier, and Guardians of the Galaxy. It also teases the events of Phase 3.
Agents of SHIELD Season 2: Scars - S.O.S.
Scars acknowledges the events of Age of Ultron, and then the series moves on with its own story.
Ant Man
The film will presumably acknowledge the events of Ultron, but who knows. Its just the next film to be released.
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