Wolverine's journey, in order
To watch the Wolverine movies in order, start with X-Men Origins: Wolverine, then X-Men and X2. That's 8 out so far, about 16 hours, ending with Deadpool & Wolverine.
Hugh Jackman played Wolverine for more than 20 years. This is Logan's own story, from his origin to his last stand, skipping the prequels he only visits briefly.
Updated
The Wolverine movies in order
X-Men Origins: Wolverine
Logan's past, and how he got his adamantium claws.
X-Men
Logan meets Rogue and joins the X-Men.
X2
Logan finds the man behind his past, William Stryker.
X-Men: The Last Stand
Jean Grey returns as the Phoenix.
The Wolverine
Logan in Japan, haunted by Jean.
X-Men: Days of Future Past
Logan is sent back to 1973 to change history.
Logan
An old Logan's last journey, in 2029.
Deadpool & Wolverine
Deadpool recruits a different Wolverine, into the MCU.
Also worth watching
X-Men: Apocalypse
A short, bloody appearance at Alkali Lake.
Questions
What order should I watch the Wolverine movies in?
Start with X-Men Origins: Wolverine, then X-Men and X2, and follow the list above: 8 in all, ending with Deadpool & Wolverine.
How long does it take to watch all of the Wolverine movies?
About 16 hours for the 8 out so far.
Where does Logan fit in the X-Men timeline?
It's set in 2029, after the new future created in Days of Future Past, and it was made as Hugh Jackman's farewell to the role.
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