An astute observer of the realms of both politics and portraiture must by now know that Rudy Giuliani is a man of many faces. He's America's mayor, a gun-hating 'bortion-craving conservative. He frowns on civil liberties. He's married, then unmarried and then married again, sometimes to cousins. And yet Catholic. He had cancer. He's a pupa, a chrysalis and a butterfly! Also he is the World Trade Center. Through the throes of his complex and multi-hued transformations, Philip Burke has captured the man for the pages of the New York Observer and sometimes for the New Yorker. What can these paintings tell us about their subject—and hey, about ourselves?

The first internet-extent Philip Burke Giuliani portrait dates back to a May 29, 2000 Observer piece. It was 12 days after Giuliani had announced that he and his wife had separated. The work features a bespectacled Giuliani, his head cocked slighty. His hawkish features are softened by a certain challenging directness that hovers between confrontation and vulnerability. His gray hair, soon enough to evaporate, still crowds the horizon of his head. His hands are small and red and clasped together like a penitent asking the forgiveness of the city. The painting is available for $30,500.00 through the LB Madison Gallery.

To illustrate Jason Horowitz's article about Rudy's prenatal presidential campaign, Burke drew on the classic 1994 comedy Junior, in which Arnold Schwarzenegger plays an impregnated man. Like Ulysses, allusion and multivalence course through and below the work. The reference to Junior, which starred a liberal Republican Governor of California, underscores what Giuliani had hoped might have been a reputation as a uniter. Sadly, it was not to be! His presidential pregnancy,

surely showing precociously for its first trimester, was on the rocks. His buffalo stance on abortion—he is "ok" with it and "ok" with not it—raised the question whether his nascent dreams for the White House should be terminated early. In this picture, Rudy still wears the same expression as he did in 2000. But as his presidential star ascended, that would all change.

In the latest representation of Giuliani, accompanying this week's cover story "Rudy's Doin' It," the pear-shaped Giuliani is gone. In fact, leading in the Republican field, Giuliani's legs look like tiny dangling participles unable to support his massive torso. His face has gotten fatter.

The worried creases of his forehead (a penitent mayor, a worried candidate) have disappeared. Instead, his lipless mouth is parted in a supercilious smile. Farewell Giuliani of Amadou Diallo. Hello America's Mayor! Also, there's a cray-cray looking bitch next to him. That would be his newest wife. This Giuliani borders on Cro-Magnon. His knuckles barely clear the floor. He's wearing clown shoes. As Giuliani becomes a caricature for the public, so too does his caricaturist give free reign to his malevolent dysmorphic pen.

Recently, the New Yorker got in on some Burke action, recruiting the artist to illustrate a piece that is basically just a longer version of the Observer one.

Gone are the scurvy yellow and gangreens of Burke's work for the Observer. Rudy's skin is ruddy. His cheeks are rosy. The eyes squint but in the New Yorker they glimmer too. His chin, in one publication a crooked grotesque cantilever, is in the other straightened into a comforting gentle "U." But compared to earlier Giuliani's, it's safe to say that his most recent incarnations are looking entirely too presidential.