Iron Man's journey, in order
To watch the Iron Man movies in order, start with Iron Man, then Iron Man 2 and The Avengers. That's 9 out so far, about 21 hours, ending with Avengers: Endgame.
Tony Stark started the Marvel Cinematic Universe, and his story runs through more than his own three films. This is every film that moves it on, from building the first suit in a cave to Avengers: Endgame.
Updated
The Iron Man movies in order

Iron Man
Tony builds his first suit and tells the world he's Iron Man.

Iron Man 2
The palladium in his chest is killing him, and S.H.I.E.L.D. comes calling.

The Avengers
He joins the Avengers, and what he sees in New York stays with him.

Iron Man 3
Dealing with the aftermath of New York, and the Mandarin.

Avengers: Age of Ultron
His plan to protect the world creates Ultron.

Captain America: Civil War
He backs the Sokovia Accords and ends up fighting Steve Rogers.

Spider-Man: Homecoming
He becomes Peter Parker's mentor.

Avengers: Infinity War
He finally faces the threat he's feared since New York.

Avengers: Endgame
The end of Tony Stark's story.
Also worth watching

Spider-Man: Far From Home
Peter Parker lives in Tony's shadow and deals with his legacy.

Ironheart
Riri Williams builds her own suit, picking up where Iron Man left off.
Questions
What order should I watch the Iron Man movies in?
Start with Iron Man, then Iron Man 2 and The Avengers, and follow the list above: 9 in all, ending with Avengers: Endgame.
How long does it take to watch all of the Iron Man movies?
About 21 hours for the 9 out so far.
Do I need to watch Iron Man 2 and 3?
They're the weakest link to the bigger story, but both matter to Tony: Iron Man 2 introduces Black Widow and Nick Fury's plans, and Iron Man 3 shows how New York changed him.
More to watch in order
- The full Marvel watch order
- Spider-Man movies in order
- Black Panther movies in order
- Avengers movies in order
- Infinity Saga in order
- Guardians of the Galaxy movies in order
- Captain America movies in order
- Thor movies in order
- Hulk movies in order
- Black Widow movies in order
- Doctor Strange movies in order
- Scarlet Witch and Vision in order
- Loki in order
- Ant-Man movies in order
- Captain Marvel movies in order
- All 44 watch paths
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