Today I'm considering a batch of "fun" Gandalfs. These are illustrations for The Hobbit considered as a children's book (which, of course, it definitely is, but not uniquely so: it tends to span interest through all age groups and can be illustrated to appeal to any level of reader), for a t-shirt, and for a comic book parody. The odd thing about them is that they all have various levels of "Gandalfishness"; if someone points to them and says, "That's Gandalf," you could very well reply, "Oh, yes, I see it," but out of context I wonder if you would recognize them.
The first Gandalf is from the 1975 Rumanian translation of The Hobbit. This Gandalf has a broad fan of a beard, and wears leggings instead of a robe down to his boots. This would be much more practical for wandering, I suppose, but not so iconic as the wizard's robe.
The second Gandalf is from the 1976 Russian translation of The Hobbit. This Gandalf's hat is flat on top, rather than pointed, and sports a peacock feather; more appropriate within the "legendarium", perhaps, for Tom Bombadil than Gandalf. Note the high-heeled boots with pointed toes.
The third Gandalf is from the 1962 Portuguese translation of The Hobbit. I get a rather Calvin and Hobbes vibe off these pictures, probably from the round eyes (this couldn't have existed at the time of course, years before the comic strip). Tolkien knew these illustrations and considered them too "Disneyfied" to be appropriate to his work.
The fourth Gandalf is from that line of t-shirts from the 1970's; no artist is listed, but I assume it is the same that did the Bilbo Baggins shirt from a prior post, Susan Greenwood Sweeton.
The fifth Gandalf is Gondeaf the Wizard from Wally Wood's Plop! comic story, "The King of the Ring." When Gondeaf taps Froydo Biggits, a Habit, to destroy the ring and its' master, Souron, Froydo asks with annoyance, "Why me? Why can't you do it?" Gondeaf explains that since he's a great and powerful wizard, if the Ring made him evil, it would be terrible, but if Froydo was corrupted, it wouldn't matter. Accompanied by some knock-off Disney dwarves and Snyder, the Prince Valiant look-alike "secret king of the world," Froydo's journey is bedevilled by the Nazighouls, Schlob the giant spider, and Glum, whom the Ring has turned into "a rotten evil swamp frog." When Froydo finally pushes Glum into the volcano with the Ring, it explodes, blowing the accursed trinket right into the hand of Gondeaf, who promptly declares that since he was around the Ring a long time, he is now evil. He puts the Ring on and disappears with the comic title's trademark sound effect, PLOP! Wood was a great comic book artist, and I think his story shows great humorous affection for the tale, as well as an understanding of (as opposed to simply mocking) themes and ideas behind the story.