[Note: The following information was sent to Amok for his contribution to the Fantasy Flight Games artbook.]
These are all Targaryens, of course, so there should be a strong family resemblence from portrait to portrait. All of them (except as noted) will have the purple eyes and silver-gold hair for which House Targaryen is noted. All of them should be wearing crowns... the same crown in many of the pix, though it will change once or twice along the way, as noted.
The hard part will be making each of the kings an individual, despite the similarities, and evoking each one's character through facial features, pose, clothing, background, and other elements in the portrait.
Here's the lineup:
AEGON I. Aegon the Conquerer. The prototypical Targaryen. A warrior, tall, powerful, broad shouldered. Very charismatic and commanding. Should be shown in his battle armor, perhaps a shirt of black scales, greaves, gauntlets, a flowing cloak. His sword in hand (Blackfyre, a Valyrian steel blade). His hair cut short, no longer than the bottom of his ears. His crown is a simple circle of Valyrian steel set with big square-cut rubies.
AENYS I. A weakling. As tall as his father Aegon, but softer looking. Slender, weedy, dreamy. Paler eyes than Aegon, more lilac than purple. His hair curled and perfumed, all in ringlets, falling to his shoulders. A silky beard and mustache, sort of a "Three Musketeers" look, coming to a point. Dressed in velvet robes, the same lilac as his eyes, with cloth-of-gold lining and an ermine collar. Gold rings and gemstones on long, slim fingers. A different crown; this one is all gold, much larger and more elaborate. No armor. Instead of a sword, he holds a wine cup in the portrait: gold, encrusted with gems. His smile should be somehow tenuous, nervous, anxious to please.
MAEGOR I. Maegor the Cruel. Another warrior. A big man, even taller than his father Aegon, bull-like, heavy shoulders, thick neck, huge arms. On the heavy side, but more massive and square than fat. Nothing soft about him. Short hair, short beard that follows the jawline. Angry, suspicious eyes, scowling mouth. Just looking at him, you know this man is hard and brutal. No wine cup here; it's the sword again. His armor is more elaborate than Aegon's. Instead of a shirt of scale, he wears a breastplate, covered by a surcoat that displays the Targaryen three-headed dragon, red on black. He looks as though he has just come from battle, and his armor and cloak show dints, tears, bloodstains. He wears Aegon's steel-and-ruby crown, not Aenys's elaborate one.
JAEHAERYS I. The Old King. The Conciliator. Jaehaerys reigned for fifty-five years. Let's show him late in his reign as an old man, as that is how he is best remembered. Wise and dignified. Despite his years, still unstooped, but his face and hands are wrinkled, and his long white beard reaches to his waist. Dressed in flowing robes of black and gold. His crown is a simple gold band set with seven gemstones of different colors. In his hands, instead of sword or wine cup, he holds a quill pen for writing.
VISERYS I. A plump and pleasant king, raised during a time of peace and plenty. Round-faced, smiling, jolly. In his forties. No beard, but a bushy silver-gold mustache. Wearing the Jaehaerys crown, with the seven stones. Looks as though he would be great fun at a party, always telling jokes. Clad in silk brocade, dark purple.
AEGON II. A strong resemblence to his father, Viserys, but in him the playful look has been replaced by a certain petulance. A sullen look to the eyes, a pouty mouth. Holds a dagger in his hand, testing the point against his finger. Clad in armor, but he does not look like a warrior. No beard, and only a faint wispy hint of a mustache. Wears the steel-and-ruby crown of Aegon the Conquerer.
AEGON III. The Dragonbane. Clad all in black, even to his gloves. A three-headed dragon on a golden chain around his neck. Pale, lean, unsmiling. A very somber look. He looks sad, marked by the grief he carries with him. It is hard to picture him smiling. A short beard, but no mustache. His crown is a slender gold band, no ornament.
DAERON I. The Young Dragon. Only fourteen when he ascended to the throne. A warrior and conquerer. Young, clean-shaved, very handsome, long hair. Clad in an elaborate suit of gold-and-black plate, with his sword in his hand. Smiling, self-confident, very charismatic. The Alexander the Great of Westeros. He should probably be shown outdoors, with the red mountains of Dorne in the background, and his army, horses, tents, etc. Wears the Aegon crown, the steel and rubies.
BAELOR I. Baelor the Blessed. Baelor the Beloved. The septon king. No sword or armor here, only a septon's white robes tied off with a rope belt. A young man, in his early twenties, but very thin (from repeated fasts) and frail looking, with a gentle, almost beatific smile (think Jesus). One hand raised in blessing, the other holding a holy book (black leather, with a seven-pointed star stamped on the cover in gold leaf). His long hair and beard remind one of Jesus too, although Baelor's are the typical Targaryen silver-gold color. Wears a crown of flowers and vines.
VISERYS II. Came to the throne quite late, when he was in his fifties. Clean-shaved, with long hair, a prominent nose, bushy eyebrows, a shrewd and calculating look about his mouth and eyes. Coins in his hand. He wears the simple crown of Aegon III Dragonbane.
AEGON IV. Aegon the Unworthy. He began his realm when he was young and handsome, and ended it old and corrupt. To provide some variety in the portraits, let us go with the older Aegon. By the end he was bloated, fat, corrupt. His eyes almost lost in the fat of his face, his legs too weak to support his belly, his mouth small and mean. His clothing should be silk and satin, bright and rich, and he would have lots of gold and gemstones about him; a chain, rings, etc. A big beard, meant to help hide his round cheeks and double chin (it doesn't). The Henry VIII of Westeros. His crown is a new one, huge and heavy, red gold, each of its points a dragon's head with gemstone eyes.
DAERON II. Daeron the Good. A thoughtful face, pale, dignified, kindly Not a warrior by any means; round-shouldered, with thin legs and a small pot belly. His face has a certain quiet strength, though, and his eyes are clear and full of resolve. In his forties. In his hands is a parchment treaty. Wears his father's elaborate dragon crown.
AERYS I. Bookish. Spindly and stooped, his robes rich and elaborate but soiled, as if he has forgotten to change them. Long straight hair, long thin face, long thin mustache, long pointed beard. In his hand is an old scroll, and other books and scrolls are visible in the portrait. His eyes red-rimmed from reading. The dragon crown is atop a pile of books, as if he has forgotten to put it on.
MAEKAR I. There's an excellent depiction of a younger Maekar in THE HEDGE KNIGHT graphic novel. As king, Maekar would look much the same, only older. A certain weariness about him, but strength as well. Armored, with a spiked mace in his hand (blood on one of the spikes). His crown is black iron and red gold, sharply pointed. His surcoat shows his personal arms; the Targaryen three-headed dragon, four times (two above, two below).
AEGON V. Aegon the Unlikely. Egg of THE HEDGE KNIGHT, grown up. Show him as a man in his thirties, with his hair falling to his collar. Tall, slender, a slight smile. Large, thoughtful eyes, very deep purple. His hand resting on a map of Westeros. Wears the simple crown of the Dragonbane. Handsome, strong yet somehow kindly, approachable.
JAEHAERYS II. Amiable, clever, sickly (he died young). Pale and frail, with very large purple eyes. Shoulder-length hair, a silky beard, a tired smile. One arm concealed by the drape of his cape. Wears Maekar's crown.
AERYS II. The Mad King. Only in his forties when he died, but he looked much older. Very thin (he was afraid of being poisoned) and gaunt, with wild, tangled hair past his shoulders, and fingernails almost a foot long (he would not allow blades in his presence, even to cut his hair and trim his beard). Wears the big, elaborate crown of Aegon the Unworthy.
VISERYS III. The Beggar King. No crown. Perhaps he should be shown in tattered beggar's robes and cloak.
DAENERYS I. Daenerys Stormborn. No description necessary, I assume. Show her wearing the three-headed dragon crown she was given in Qarth, as described in A CLASH OF KING. Might be good to include the three dragons in the picture. Show them very young, as hatchings, one in her lap, one wrapped around her arm and shoulder, one flying just above her.
And that's it.