At the risk of seeing this blog lurch even further in the direction of "Which Dead Celebrity Caricature Can I Post This Week?", here's a couple of old Ted Kennedy illos from the heyday of New York Press.
I was a regular contributor to NYPress from the early 1990's through the mid-2000's. My drawings often accompanied columns by Alexander Cockburn, John Strausbaugh and J.R. Taylor, but for the entirety of 1999, I provided the art for NYPress Publisher Russ Smith's notoriously Right-leaning MUGGER column.
Typically, these MUGGER illos started off with Smith phoning me on a Friday to describe whatever concept he had in mind. In one or two instances, I may have massaged Smith's concepts slightly, but generally I drew exactly what he asked for. There were dozens of illos slagging the Clintons, Al Gore, & other Democrats, while others were aimed at NYC media figures like Tina Brown, Kurt Andersen, etc.
Here's a MUGGER illo from May 1999, showing a tuxedo-clad Ted Kennedy handing the "Profiles In Courage" award to John McCain, (dressed as an extra from one of the "Rambo" films). Revisiting this one, I cringe just a bit at my McCain likeness, (my McCains would improve over the subsequent decade), but I like to think the Ted Kennedy likeness still holds up.
Next we have a cover illo for New York Press from April 2001. This was an especially fun one for me, because I got to switch into horror movie mode, (always a happy place for me). Here we see mad scientist Ted Kennedy unleashing a new generation of toothy Kennedy offspring upon the political scene, while the ghostly head of JFK looks on approvingly. Art direction by my pal, longtime NYPress art baron Michael Gentile, of course.