When did Indiana Jones learn to fly a plane?

Question

Consider the following sets of dialogue.

The first is from Indiana Jones and the Temple of Doom (1984) and the second from Indiana Jones and the Last Crusade (1989).

From Temple of Doom:

Willie: No one's flying the plane!

Indy: Oh, boy...

Willie: They've all gone! You know how to fly, don't you?

Indy: No. Do you?

Willie: Oh, no. Oh, my god!

Indy: How hard can it be?

From Last Crusade:

Indy: Come on, Dad. Come on!

Jones Sr.: I didn't know you could fly a plane.

Indy: Fly, yes. Land, no.

So on to my question. When did Indy learn to fly a plane? Are we meant to understand that he's learned to fly since the events of Temple? Or are we meant to understand that due to the events of Temple, he now has a basic working knowledge of how to fly a plane?

Answer 1

According to the Lost Journal of Indiana Jones, he learned how to fly a Ford Tri-Motor Airplane following the events of The Temple of Doom.

Determining that killing Jones was worth the cost of the plane, Lao Che signaled the pilot and co-pilot to ditch the plane. After refueling in Chungking, the plane traveled west instead of south towards the scheduled destination. While the passengers slept, the pilots dumped the fuel, took the only parachutes aboard and jumped to safety over the eastern Siwalik range2. Jones and his companions awoke, realized that a crash was unavoidable, and jumped out of the plane with an inflatable raft. The plane crashed into a mountaintop near the Pindari Glacier.

After the encounter, Jones found an instruction manual for a Ford Trimotor and kept it in his journal, along with a note to learn how to fly a plane. By 1938, he had learned how to fly a plane, but not land.

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Note: The Temple of Doom is considered a prequel as it is set in 1935 and Raiders of the Lost Ark is set in 1936. So, Indiana Jones learned to fly (but not land) in the time frame between The Temple of Doom and The Last Crusade.

Answer 2

Despite the accepted answer, I think the more obvious answer is that this is just a (self-referential) joke.

So most likely Indiana Jones never actually learned to fly a plane, he kept one in the air in Temple of Doom (which technically checks the "flying" part), but he obviously botched the landing. So he answers truthfully: Fly? Yes. Land? No.

Now explaining jokes is always funny, but that actually works as a short standalone sketch and if you've seen Temple of Doom, you'd also get a nice throwback to that adventure.

Now with regards to that Lost journal of Indiana Jones. That was apparently released in 2008 for the Crystal Skull movie so not sure that should count as canon with regards to the original trilogy.

But if you consider it canon and consider that many people (maybe even the writers of this log) don't actually realize that Temple of Doom is actually a prequel and not a sequel to Raiders of the Lost Ark. You might even include Raiders in that joke:

Like in "Raiders of the Lost Ark" he escapes the turmoil after the warrior temple with the help of his pilot, who has a pet snake(!). So as I'd imagine that wasn't a nice experience for a person with a snakephobia, that might be the origin of:

"Indiana comments in a to-do list that he must learn how to fly a plane."

Then in "Temple of Doom" he actually flies a plane but crashes it. Or in other words he can now cross "flying a plane" off the to-do list but instead:

Later on, he makes a new to-do list that includes learning how to land a plane.

You know the crucial part that he didn't consider last time.

While the "By 1938, he had learned how to fly a plane, but not land", probably has it backwards. 1938 is the in-universe year in which The Last Crusade takes place, so we know that he didn't learn to land until then ... well because of that very line of dialogue that you quote in the question.

So if you consider the chronological progression (Temple, Raiders, Crusade) then the lost journal doesn't actually make all too much sense here. Because if Indiana Jones would have really picked up flying AFTER Temple of Doom (he obviously couldn't fly in that adventure), he wouldn't have gotten far until Raiders we're he still has a pilot. But most crucially: Why would he have not gotten to the landing part by 1938! And I'm not talking about him being a slow learner, but about the fact that in Temple of Doom he literally had an experience that would have taught him that landing a plane is the most important part of all of flying.

So I'd suspect that the writers of that journal thought the progression is Raiders, Temple, Crusade and then made funny references to these three movies.