George Macy of the Heritage Press invited Rockwell to illustrate Mark Twain's Tom Sawyer and Huckleberry Finn. Rockwell was passionate about this opportunity writing, "It's fun to do a really good book, but only the best titles give me any satisfaction. Mark Twain's Tom Sawyer and Huckleberry Finn are of the type I enjoy. These had long intrigued me, so when [I was] invited to illustrate them, I was able to throw myself into the task with real enthusiasm."
To capture the authentic details of the story's setting, Rockwell visited Hannibal, Missouri. At the time he was the only illustrator of the Tom Sawyer stories who went to the site. When describing the experience Rockwell claimed that "The whole town of Hannibal lives in the memories of Tom and Huck-or rather, of Mark Twain. He depicted things just as they actually were. The Tom sawyer story is truly autobiographical in the sense that even if Mark Twain didn't personally do some of the things attributed to Tom, he understood exactly how Tom would have done them. That made my task as illustrator an exceptionally interesting one." -Norman Rockwell from Arthur L. Guptill's Norman Rockwell Illustrator
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