This is a really old topic, but I’ll share anyway.
I began Discworld with Color of Magic, then Light Fantastic, then Equal Rites and Mort. It was the last two that really got me into the series. I think that Sourcery might have been the last one I read in order of publication, though I can’t recall, since it was twenty years ago.
At any rate, for many, many years I did not like Rincewind or his stories. It took me forever to read The Last Continent or Interesting Times—in fact, I only read them in the last 12 months or so via audiobooks, and they’re two of the last DW book I ever read!
Rincewind’s tales were just too bizarre and outlandish to my taste (except Interesting Times.) Another thing was Josh Kirby’s illustrations of him as an old wizard. I normally actually really like Kirby’s pictures (though it’s hard to tell half the time what’s going on)—in fact, I give them credit for getting me into the series since I picked up Color of Magic on a bookstore shelf and felt interested in it because of the weird cover. Who says you can’t judge a book by its cover? However, his depiction of Rincewind turned me off. Unlike Granny Weatherwax, for whom there was sufficient textual description for me to ignore Kirby’s illustration of her, I couldn’t quite separate Rincewind from his Kirby image or the headache-inducing settings of his stories.
But then, about 3-4 years ago, three things happened:
First, I discovered Paul Kidby’s more realistic depiction of DW characters. His depiction of Rincewind completely changed my image of him. Suddenly he came alive and meshed with his stories.
Second, I began to listen to audiobooks and both Nigel Planer and Stephen Briggs do a terrific Rincewind. His defeatist, dry tones accompany the text perfectly.
Third, I read the Science of Discworld 1 and 2. At that point, my internal image of Rincewind had already improved dramatically. And he was quite awesome in those books. I can’t explain why, but I love him in those. Then I listened to the audiobooks of pretty much all his books (except Sourcery and Eric, gotta purchase those) and I found myself finally enjoying him as a character in those.
Nowadays Rincewind is not my favorite by any means, but he certainly rose in the ranks dramatically. As Rincewind might have said in dry, sarcastic tones, “Well, ain’t that nice.”