One of the biggest names in comic books these days is Alex Ross, known for painting superheroes and their adventures in strikingly photorealistic style.
Comics companies like to use Ross's portraits of iconic characters on special issues and anthologies. Collectors seek his originals and prints, and there's even a blog just for Alex Ross collectors. Currently the asking price for Ross's watercolor painting of Superman and Captain America together is $19,000.
One of Ross's masterworks, Marvels, authored by Kurt Busiek, retold the early history of the Marvel universe through the eye of an ordinary newspaperman. In another, Kingdom Come, Ross and writer Mark Waid looked ahead to the possible future of the DC universe. That original story included a middle-aged version of Dick Grayson, using the name Red Robin. But, frankly, it didn't include him much.
Indeed, I've found Ross's depictions of Robin to lack the vigor and realism he's brought to Superman, Captain Marvel, Wonder Woman, and other characters. (The biggest exception is his cover for Legends of the Dark Knight, #100, shown above, courtesy of the Grand Comics Database.) Ross's portrayals of Robin have struck me as stiff and generic, in contrast to the qualities he usually gives to Batman. See the difference on this Batman Family collectible plate.
In Mythology, a collection of Ross's work for DC Comics, editor Chip Kidd described Ross as "somewhat reluctant, at first, to do a rendition of Robin." What was the problem? The traditional character offended the artist's (and comic book fan's) sense of practicality:
The weird thing about my ever working with Robin is that, as a character, he just doesn’t make any sense. He’s the compromise Batman would never have logically made. Who would put a child at risk like that, in that garish outfit? But you can’t fight history, and I just remain faithful to it despite itself. There’s no point in trying to make his costume look tough, or menacing, or even practical. With Robin you don’t have a choice--it’s those gaudy colors or nothing.Early on, however, I'm pretty sure that Ross liked Robin a lot, in just the way that the character's creators meant young readers to. Why am I so sure? Here's the very first example of superhero art reproduced in Mythology, drawn and colored when Ross was a preschooler.
[ADDENDUM: A very new addition to Ross’s gallery of heroes.]