exactly .. the idea in the movie is that he was expecting the cup of king of kings not a carpenter

It was stupid because you'd think that Donovan would have researched something like this
to know what the real grail looked like. I mean ,it's the f'in Holy Grail.
And then when Elsa offers to choose one, she doesn't even look around, she basically just turns and grabs one without even examining it. Even someone who wasn't a historian would know that it wouldn't have been made of gold just by looking at the painting of the last supper which unless you'd been living under a rock you'd have seen that painting at least once in a book. Plus, why would you drink from it knowing if it was the wrong one you'd die. I would have made her or Jones drink from it first. Course then the plot would have changed. That's movies for you. The bad guy always makes a stupid mistake

If you thought you were in the presence of one of the greatest artefacts in human history, we would see how your 'common sense' would hold up.
The dude was completely overwhelmed by his emotions, his greed being chief among them. When emotion takes over human beings - yourself included - common sense is the first thing that steps out to grab a cup of coffee.
Never defend crap with 'It's just a movie'
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Where is this 150 year old Knight mentioned?
In the scene where Donovan shows Indy the tablet.
Donovan: Let me tell you another "bedtime story," Doctor Jones. After the Grail was entrusted to Joseph of Arimathaea, it disappeared and was lost for a thousand years before it was found again by three Knights of the First Crusade. Three brothers, to be exact.
Indy: I've heard this one as well. Two of these brothers walked out of the desert one hundred and fifty years after having found the Grail and began the long journey back to France. But only one of them made it. And before dying of extreme old age, he supposedly imparted his tale to a to a Franciscan friar, I think.
So that's 150 years staying with the grail - well, let's say 149 and one year for trekking back. The first crusade lasted from 1096-1099, and if we say the brothers found the grail in 1099, that means the third brother returned to France in 1249.
Edit: my maths was off.

Where is this 150 year old Knight mentioned?
I'm not being funny, I'm genuinely asking. I don't remember it.
Does the Knight himself mention it, or is it a legend that Indy/Henry or Donovan talk about?

It wasn't. He left the temple after his wound had been cleared. He was just a normal human being again.
Yet the knight who made it out of the desert died from "extreme old age", 150 years (plus an unspecified amount of time) after having found the grail. Of course, we don't know how much he drank from the grail before leaving the temple, but he didn't take the grail with him.

him dying of old age was a bit of a goof in Kingdom
It wasn't. He left the temple after his wound had been cleared. He was just a normal human being again.
He would only have a long life if he'd stayed.

Then why does Henry Sr not only have his bullet wound healed by the water of the grail, and then die later at what we can assume is a typical old age in the 40s / 50s of 60-70?
The grail can heal wounds. But just like a band-aid, it doesn't have any pro-active effects. Putting ice on your skin now isn't going to prevent a burn from hurting tomorrow. And him dying of old age in the '50s was a bit of a goof in Kingdom. They had to have an excuse for his father not being present, I guess (owing to Sean Connery turning down the part).

Then why does Henry Sr not only have his bullet wound healed by the water of the grail, and then die later at what we can assume is a typical old age in the 40s / 50s of 60-70?

First, Donovan is an arrogant beep and we all know it.
Second, if you're in a room with your worst enemy, are you going to let him have the ultimate thing that can keep him alive forever? beep no, YOU'LL take that, even on the off-chance you'll die.
Drinking from the grail won't make you immune to bullets, it simply means you won't die from old age. And they all knew as much. Remember the two knights who walked out of the desert? One of them died
in
the desert, and the other died from
extreme old age
, suggesting he had once drunk from the grail. But in order to live for ever, you have to keep drinking from it. So what harm could there possibly be, from Donovan's perspective, in letting Indy drink from the true grail?

First, Donovan is an arrogant beep and we all know it.
Second, if you're in a room with your worst enemy, are you going to let him have the ultimate thing that can keep him alive forever? beep no, YOU'LL take that, even on the off-chance you'll die.

Villains like any person make mistakes

Who was Donovan was he the guy who rode off on a horse at the end?

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It is definitely a plot hole but let's be honest it's the least of this films problems.
"I really wish Gia and Claire had became Tanner" - Honeybeefine

He was so caught up in what he thought was his ultimate victory that he let his pride and greed get the better of him.
Arrogant people thinking they can benefit from toying with Holy Artifacts is a recurring theme in this series. Belloq did the same thing when he thought he'd be able to fool the Ark into thinking he was a Jewish Holy Man reciting the Jewish Prayer to activate the Ark.

Best response yet.

Yeah, Donovan really wasn't that intelligent. He didn't even bother to look up what the grail looked like before he went after it. And he places his life entirely in the trust of Elsa. Seriously, there was only a 1/50 chance he would choose the right grail, and he just has her pick one willy nilly.
However, that said, there is at least one theory that could explain his rash want to throw his life away. Not only was he tempted by the promise of eternal life, but it almost seemed like he was being seduced by the supernatural aura of the golden, jewel-embedded goblet. Look at his face when he gazes on it and says "it's more beautiful than I could ever have imagined." It's as if he was being hypnotized into drinking from it, and was compelled into choosing poorly by his greed and vanity. After all, Satan thrives on deception and false promises.
~ I'm a 21st century man and I don't wanna be here.

A) See, nobody at that point, actually knew that the grails longevity effect wears off if you exit the temple. They believed drinking from the grail grants immortality, period. As such, Donovan did not want Indy to receive this gift.
B) As he saw the cup Elsa had chosen, Don instantly believed it to be the right one, because she was the expert, and because that cup was the most glorious and magnificent one. He didn't doubt at all he had the right one.
I'm having trouble with a patient of mine; he's a teenage drug addict who's being molested. By me.

That's my interpretation as well, but I do see kinda as a ambiguous detail to some people.

First, lets stop saying "live forever". You do not live forever after taking a sip from the cup. In order to really keep living, you have to actually stay in the temple and continually drink from the cup, like the knight did.
And yes I agree, it was very stupid of Donovan to take the first sip himself. He should've had Indy take a sip first and see what happens, or he could've told Elsa to drink from it first.

Why would Donovan risk giving his arch nemesis (Jones) eternal life??
What if Indy did try the holy water out of the correct grail? He'd live forever! Donovan would be toast.
How would that make Donovan toast? It's not like Indy would then have super powers or anything. The eternal life implied by the grail was never more than an anti-agapic: supposedly "the gift of youth" (as Donovan describes it at one point), and never ageing. This doesn't mean that you can't be killed. And indeed, Donovan knows that one sip won't suffice: the one knight who made it out of the desert died of extreme old age, suggesting he had drunk from the cup but he did die.

Why would Donovan risk giving his arch nemesis (Jones) eternal life??
What if Indy did try the holy water out of the correct grail? He'd live forever! Donovan would be toast.

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