Once upon a time, I would have been able to rank these games confidently, but as I’ve gotten older, I find it harder to do so. I’m sure there’s a whole book that can be written about the reasoning behind that, so I’ll skip right to how the “ranking” works in my mind, right now.
Tier 1
Chronologically: The Secret of Monkey Island, Monkey Island 2: LeChuck’s Revenge, Return to Monkey Island
Having gone through Return a handful of times now, it increasingly is becoming hard to separate the three. Return certainly rides on a different narrative structure -- and doesn’t have the advantage of thirty years of lovin' -- but the three fit together perfectly for me. I’ve said enough about the two first games over the past twenty-plus years around these parts, and will have plenty to say about Return after I’ve digested it further. If I was to rank them, in all likelihood it would look like this:
1. LeChuck’s Revenge
2. The Secret of Monkey Island
3. Return to Monkey Island
Tier 2
Tales of Monkey Island
It has its issues and inconsistencies (as generally is the case with TTG’s episodic nature), but the tone of the game is the closest to the non-Gilbert-lead Monkey Islands. In that sense, with Tier 1 taken into consideration, Tales is the logical #4. I guess I'm a Gilbert/Grossman-head at heart.
4. Tales of Monkey Island
Tier 3
Chronologically: Curse of Monkey Island, Escape from Monkey Island
This one is tougher. Escape is deeply inconsistent -- no need to get into those details -- but the dialogue is fresh and funny (albeit sometimes awkwardly so). All very Stemmle-y.
Curse is consistent throughout, in that it feels like it has zero ambitions being anything but cute in story and dialogue. It’s funny at times, but it never leaves me feeling... anything... after playing it. Escape at least has a pinch of satire. Thus:
5. Escape from Monkey Island
6. Curse of Monkey Island