Why is King Henry disappointed in his son, Prince Hal?

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It's worthwhile to also consider how the king cannot help but compare Hal to himself. While upbraiding Hal for his unseemly behavior, he tells of how he himself managed to win the hearts of his people: 

Had I so lavish of my presence been,   So common-hackney'd in the eyes of men, 40   So stale and cheap to vulgar company,   Opinion, that did help me to the crown,   Had still kept loyal to possession   And left me in reputeless banishment,   A fellow of no mark nor likelihood. 45   By being seldom seen, I could not stir   But like a comet I was wonder'd at;   That men would tell their children 'This is he;'   Others would say 'Where, which is Bolingbroke?'   And then I stole all courtesy from heaven, 50   And dress'd myself in such humility   That I did pluck allegiance from men's hearts,   Loud shouts and salutations from their mouths,   Even in the presence of the crowned king.   Thus did I keep my person fresh and new; 55   My presence, like a robe pontifical,   Ne'er seen but wonder'd at: and so my state,   Seldom but sumptuous, showed like a feast   And won by rareness such solemnity.


The king is so focused on how he managed to "prove" himself that he is blind to the possibility that his own son is equally shrewd. 

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King Henry IV is disappointed in his son and heir-apparent Prince Hal because Hal appears to be taking his responsibilities very lightly and is given to behavior that does not fit his royal role. Hal spends all his time with low companions, such as Falstaff, and even engages in criminal activity with them. King Henry cannot resist comparing the madcap behavior of his son with the valiant and "kinglike" deeds of Hotspur, for the purposes of the drama brought forward as a counterpart and foil for Prince Hal:

Yea, there thou makest me sad, and makest me sin
In envy that my Lord Northumberland
Should be the father to so blest a son,--
A son who is the theme of honour's tongue;
Amongst a grove, the very straightest plant;
Who is sweet Fortune's minion and her pride:
Whilst I, by looking on the praise of him,
See riot and dishonour stain the brow
Of my young Harry. (Act I, scene 1)

However, when King Henry finally calls Prince Hal to account in a private conference, and accuses him face to face,

But thou dost, in thy passages of life,
Make me believe that thou art only mark'd
For the hot vengeance and the rod of Heaven
To punish my mistreadings. Tell me else,
Could such inordinate and low desires,
Such poor, such base, such lewd, such mean attempts,
Such barren pleasures, rude society,
As thou art match'd withal and grafted to,
Accompany the greatness of thy blood,
And hold their level with thy princely heart? (Act III, Scene 2)

the Prince is quick to reassure his father that he will not disappoint him when called upon to fulfill the duties of his position:

This, in the name of God, I promise here:
The which if I perform, and do survive,
I do beseech your Majesty, may salve
The long-grown wounds of my intemperance:
If not, the end of life cancels all bands;
And I will die a hundred thousand deaths
Ere break the smallest parcel of this vow. (Act III, Scene 2)

This satisfies the King's mind, and even though Prince Hal is still speaking of his royal father somewhat facetiously in the next scene ("I am good friends with my father, and may do any thing"), he displays a new focus on his duties:

Meet me to-morrow, Jack, i' the Temple-hall
At two o'clock in th' afternoon:
There shalt thou know thy charge; and there receive
Money and order for their furniture.
The land is burning; Percy stands on high;
And either they or we must lower lie. (Act III, Scene 3)

Prince Hal has not forsaken the company of Falstaff and the rest, but his change of attitude towards his duties reassures his father to the point that the King is willing to acknowledge Prince Hal his successor:

And, Prince of Wales, so dare we venture thee,
Albeit considerations infinite
Do make against it.-- (Act V, Scene 1)

When Prince Hal rescues the King from death in battle at the hands of Douglas, this marks the final resolution of the King's worries concerning the Prince:

Thou hast redeem'd thy lost opinion;
And show'd thou makest some tender of my life,
In this fair rescue thou hast brought to me. (Act V, Scene 4)

Thus, over the course of the play, King Henry's doubts about his son's morals and capability, which have even led him to believe that Prince Hal would welcome his death, are worn down by the Prince's evident reapplication to his royal duties. By the end, although Falstaff and the Prince's other low companions have not yet been openly rejected, Prince Hal has demonstrated his sense of duty and his seriousness.

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