20. Mark Twain
Get your facts first, and then you can distort them as much as you please.
Yes, Samuel Clemens was born in Florida- Florida, Missouri that is. (Hence the trick clue!)
The top 20 of my list is crowded with statesmen and innovators, but it's fitting to kick it off with America's greatest man of letters. Yes, I know that if you walk into any English department, there will be a list of great American writers that are generally regarded above Mark Twain: Herman Melville, Nathaniel Hawthorne, William Faulkner, F. Scott Fitzgerald, Ernest Hemingway, John Steinbeck, just to name a few.
But this is a list of great Americans, and Twain has to top all of those guys, even Hemingway (who also made this list a while back) because he is the quintessential American writer. He is the first one everybody thinks of, the classic name, arguably the greatest observer of our society. Adventures of Huckleberry Finn, more so than Moby **** or The Great Gatsby, really is THE American novel. And Tom Sawyer is arguably our greatest fictional creation (with all apologies to Superman and Batman.)
Twain was a liberal but no extremist. He was a humorist and a satirist but never a cynic. There is a sense of optimism which is evident in all of his writings, a love for America and what it could be. He was definitely a moralist but didn't look down on anyone, and always avoided patronizing people. He hated lecturing and being lectured to. And even though his values were by and large progressive, he defended the strengths of the conservative rural society in which he was raised. Very clearly one of our greatest Americans.
Up next: the Founding Father who, as a lawyer, defended the British soldiers accused of murder in the Boston Massacre...