The Youth of Alexander the Great
Four Stories of Prince Al (356-323 B.C.)
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Falstaff
Marry, then, sweet wag, when thou art king, let not
us that are squires of the night's body be called
thieves of the day's beauty: let us be Diana's
foresters, gentlemen of the shade, minions of the
moon; and let men say we be men of good government,
being governed, as the sea is, by our noble and
chaste mistress the moon, under whose countenance we steal.
Prince Henry
Thou sayest well, and it holds well too; for the
fortune of us that are the moon's men doth ebb and
flow like the sea, being governed, as the sea is,
by the moon. As, for proof, now: a purse of gold
most resolutely snatched on Monday night and most
dissolutely spent on Tuesday morning; got with
swearing 'Lay by' and spent with crying 'Bring in;'
now in as low an ebb as the foot of the ladder
and by and by in as high a flow as the ridge of the gallows.
Henry IV, Part I, I.ii
It's hard enough living up to the expectations of one's parents, but when one has a great or powerful father whom the whole world admires, it must be very tempting just to throw in the towel. As the son of such a man, the young Prince Alexander (or Prince Hal) would have had no lack of would-be friends, young men with whom he could relax, get up to mischief, tear out his hair at the latest paternal victory,
Whenever he heard Philip had taken any town of importance, or won any signal victory, instead of rejoicing at it altogether, he would tell his companions that his father would anticipate everything, and leave him and them no opportunities of performing great and illustrious actions. For being more bent upon action and glory than either upon pleasure or riches, he esteemed all that he should receive from his father as a diminution and prevention of his own future achievements; and would have chosen rather to succeed to a kingdom involved in troubles and wars, which would have afforded him frequent exercise of his courage, and a large field of honour, than to one already flourishing and settled, where his inheritance would be an inactive life, and the mere enjoyment of wealth and luxury.or get drunk -- although in Alexander's early years, it would have been hard to surpass his father's alcoholic stamina at symposia (drinking parties).
Plutarch Life of Alexander
What else did the young prince do while waiting for his turn to rule, besides studying the Iliad and Euripides, absorbing military discipline from his tutor (Leonidas), then music with Lysimachus, and, from the age of 13-16 (along with some of his friends in the Macedonian aristocracy), philosophy and other information from his tutor Aristotle?
I haven't counted, but I'm sure there are more legends and anecdotes told about Alexander than almost any other historical figure. Without doing any research, you've probably heard of two: the taming of Bucephalus and the cutting of the Gordian Knot. Of these, only the stallion story belongs to the time of Alexander's youth.
Although pride is there from the beginning, the later anecdotes show sides of Alexander that are invisible in the young equestrian. Reckless and courageous sides that may not be thought of as desirable in a son, but were necessary for him to fulfill his political ambitions.
Skip Bucepahlus and go on to the second anecdote.
1. Bucephalus
Philip, King of Macedon, was inspecting Bucephalus, a black stallion that had been offered for sale. The horse was unmanageable, so Philip ordered it removed, but Alexander objected that they were losing a great horse just because they didn't know how to handle it. 
When Philip challenged his son to make good on his bravado, Alexander said he would pay for the horse if he couldn't master it. Since the price was an astronomical 13 talents, the adults laughed.
But Alexander was given his chance. He turned the head of the horse towards the sun so it wouldn't see the shadow that Alexander had noticed it seemd to fear. Then Alexander walked beside the horse, talking to it and calming it down until he felt it was propitious to mount. After a short gallop, Alexander returned to his father and the other men, in full control of the horse.
The men applauded and Philip said, according to Plutarch, "O my son, look thee out a kingdom equal to and worthy of thyself, for Macedonia is too little for thee."
2. The End of his Schooling
Alexander's tuition ended when he was 16, at which time Philip, about to leave for the Hellespont, handed his son the royal seal.
While the king was away, a Thracian tribe, the Maedi, rebelled against Macedonian rule. Alexander led an expedition against the insurgents, subdued the rebels, and renamed the Macedonian colony Alexandropolis.
Shortly thereafter Alexander joined his father. On their booty-laden return from the Danube, another Thracian tribe attacked. Alexander is said to have courageously saved his father's life.
3. Philip Marries Cleopatra (337 B.C.)
When Alexander was born to Philip's fourth wife, Olympias (c. 356), the Queen's status in Philip's household was assured -- at least for a time. Neither Olympias nor any of the other queens were Macedonian natives, so instead of lineage, preferential status was conferred on the basis of production of heirs. Alexander was the only fully competent male child.
However, when Alexander was about 19, Philip married again, and this time to a Macedonian named Cleopatra. At the wedding feast, Cleopatra's uncle Attalus prayed aloud that his daughter produce a legal heir to the kingdom.
Alexander, fearful of his own position and insulted by the implication that he was illegitimate, threw a cup of wine at Attalus and said "what, am I then a bastard?" Philip intervened, but instead of taking his son's side, he drew a sword to use against him. As luck would have it, Philip was drunk and fell down.
Humiliated, Alexander quipped "See there," said he, "the man who makes preparations to pass out of Europe into Asia, overturned in passing from one seat to another."
At the wedding of Cleopatra, whom Philip fell in love with and married, she being much too young for him, her uncle Attalus in his drink desired the Macedonians would implore the gods to give them a lawful successor to the kingdom by his niece. This so irritated Alexander, that throwing one of the cups at his head, "You villain," said he, "what, am I then a bastard?" Then Philip, taking Attalus's part, rose up and would have run his son through; but by good fortune for them both, either his over-hasty rage, or the wine he had drunk, made his foot slip, so that he fell down on the floor.Alexander and his mother left the court. She went to her brother's court at Epirus and Alexander went to Illyria.
Plutarch Life of Alexander
Alexander was persuaded to return home by the end of that same year -- 337.
4. Pixodarus (336 B.C.)
While Alexander had been the only healthy male child, he hadn't been the only son of Philip. According to John Maxwell O'Brien, Olympias may have caused brain damage to her step-child, the other male child, Philip Arrhidaeus.
Alexander had never considered his half-brother a threat until his father and Pixodarus of Caria (part of the Persian Empire) began to discuss marriage plans between their children. Philip Arrhidaeus was to marry Pixodarus' daughter.
Alexander, persuaded by his friends or mother that the marriage was more important than Philip let on -- that it signified Alexander's replacement by his half-brother -- sent an emissary to Pixodarus countermanding the king's arrangement. The emissary insisted that not Arrhidaeus but Alexander be the bridegroom.
This was more than disobeying a parent.
When Philip found out, he was enraged, banished four of Alexander's closest friends and ordered Alexander's emissary brought home in chains.
In the end, Pixodarus decided against the alliance with Macedonia and sided, instead, with the Persian Darius III.
... for when Pixodorus, viceroy of Caria, sent Aristocritus to treat for a match between his eldest daughter and Philip's son, Arrhidaeus, hoping by this alliance to secure his assistance upon occasion, Alexander's mother, and some who pretended to be his friends, presently filled his head with tales and calumnies, as if Philip, by a splendid marriage and important alliance, were preparing the way for settling the kingdom upon Arrhidaeus. In alarm at this, he despatched Thessalus, the tragic actor, into Caria, to dispose Pixodorus to slight Arrhidaeus, both illegitimate and a fool, and rather to accept of himself for his son-in-law. This proposition was much more agreeable to Pixodorus than the former. But Philip, as soon as he was made acquainted with this transaction, went to his son's apartment, taking with him Philotas, the son of Parmenio, one of Alexander's intimate friends and companions, and there reproved him severely, and reproached him bitterly, that he should be so degenerate, and unworthy of the power he was to leave him, as to desire the alliance of a mean Carian, who was at best but the slave of a barbarous prince.Postscript
Plutarch Life of Alexander
Death of Alexander
Pausanias, a personal bodyguard, stabbed and killed Philip in the same year as the Pixodarus affair. We do not know whether Pausanias acted alone or in a conspiracy. It was suggested that Olympias may have been involved. Accusations against Alexander were levelled and dropped. But the most common explanation for the regicide is that Pausanias was angry with his king for failing to take action against Attalus. Besides insulting Alexander, Attalus had plied Pausanias with wine and then handed him over to muleteers to abuse.
Alexander the Great: The Invisible Enemy 
Online reviews of works on AlexanderDrinking to excess, according to John Maxwell O'Brien in Alexander the Great: The Invisible Enemy, was a Macedonian vice to which Alexander's father Philip was particularly devoted. Once, when a woman upon whom Philip had pronounced sentence made an appeal -- as she told the king, to a sober Philip -- he understood, sobered up and reversed his decision.
• Commentary on Arrian's History of Alexander
• Review: John Maxwell O'Brien. Alexander the Great: The Invisible Enemy.
In criticizing O'Brien's book for being little more than a reworking of Plutarch's Life of Alexander, Waldemar Heckel says it is "colourful, lively, and largely anecdotal."
Heckel also criticizes one feature of the book I found exasperating: the constant linking of obscure mythological figures.O'Brien, in his desire to link Alexander with his mythical past, strains the evidence and finds connections everywhere: the Rhodian general Memnon is described as a "man, whose namesake was slain by Achilles in the Trojan War."To me, the main problem with O'Brien's book, is using the anachronistic frame of a 20th century obsession with alcohol.
