Over the years, I’ve done a number of drawings and paintings of myself — and I’ve been fortunate enough to be the subject of drawings by a few other people. Looking back at this whole collection of portraits, it’s a bit difficult to see how they connect; If I didn’t already know what I look like, I’m not so sure that they’d add up to anything really cohesive. But maybe that’s the secret of caricatures: When they work, they exist outside the constraints of objective reality — while still managing to be truthful.

This first one, a self-portrait, was published in my college yearbook as part of a collection that included the chancellor, the student senate president, a basketball player, a cheerleader and the ever-popular professor who taught Human Sexual Biology:

This next one, also a self-portrait from my college days, is actually a five-foot-wide painting (which currently stares out into the neighborhood from the back wall of my garage):

Back in the Stone Age, when newspaper comic strips seemed like a big deal, I pitched a handful of concepts — one of which featured this pseudo-lookalike:

I’ve managed to save a few things by my friend and former co-worker David O’Keefe:

This O’Keefe sketch marked my departure from The Tampa Tribune in the mid-’90s:

As did this full-blown (and I do mean “full-blown”) caricature:

And here’s one more from the talented Mr. O’Keefe:

For a Christmas letter one year, I drew myself as Mr. Potato Head for a “Toy Story”-themed family portrait:

More recently, I included this self-portrait in one of my “Blogjam” comics:

And another recent cartoon:

But my favorite portraits may be a pair that were drawn by my youngest son, Jeremy; This one is from his Pre-Teen Period:

This last one from Jeremy (as a 15-year-old artiste) provides a glimpse of how “Old Greg” might look in 15 years:


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