While he came from a moneyed family great grandson of Mark Lyndsay McDonald, his father was an unemployed, free-spending eccentric amateur inventor.

[2][3] Hamilton later said "We lived on one of those dwindling trust funds with a hint of money in the past, but not much in the present".

Hamilton's interest in cartooning was sparked by stacks of European magazines found in the house.

[2][3] In the World Encyclopedia of Cartoons, Richard Calhoun describes Hamilton's work: His close-up renderings of features have more the quality of preliminary portrait sketches than of caricature ... His humor also tends to be of a rather personal stamp—very much New York, corporate and Ivy League in setting, and dedicated to the deflation of intellectual pretension and cliché ... those familiar with the rather hermetic environment he satirizes will laugh (or wince) at his thrusts.

Especially keen are his frequent variations upon the theme of the cocktail party—surely one of civilization's most persistent forms of self-inflicted torture.

[2] His play White Chocolate has been described as "a farce about race and class in the upper echelons of New York society.