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I checked eBay's "Completed Listings" which were sold over the last year, and there weren't any original artwork of Tony Soprano that were sold or listed for more than $350.Yeah the Hillary one was particularly cartcature-like IMO.
They'd be best off doing caricatures on a boardwalk someplace for $10 each IMO. High-end art this is not. JMO, and I admittedly am not into art so what do I know. But JMO this stuff would be worth the most in 100 years when descendants of Mike and Frank find them in a barn someplace behind a Mobilgas Pegasus while filming an episode of American Pickers v.3.0.
JMO
Most were on a "Buy It Now" option and sold for around $99.00 or less. Maybe the eBay listing was over a year ago which I can't go back that far to check.