I guess where you should start depends on what you're interested in...Let me quote a comment I made to a friend a few weeks ago on that question. ___________________________________
As for Chesterton, er, well, it depends on what you are interested in. He basically wrote in all genres (or so it seems) on every topic. He was one of the most prolific writers ever (with over fifteen million words in print). To give a few examples of his work and their influence, which I document (for the most part) on my list of Chesterton's influence (http://augustine.livejournal.com/7853.html#cutid1), let me note the following, giving only one sample from each category, just to see what you might be interested in. From there, I can give you more detail on any individual category (and I'm missing some categories, no doubt).
Novels:The Man Who Was Thursday
Terry Pratchett and Neil Gaiman dedicated their novel Good Omens to Chesterton because, according to Gaiman, they felt that while writing Good Omens they were, on a very fundamental level, "doing The Man Who Was Thursday".
Short stores:Father Brown detective stories.
Strand Magazine describes Chesterton as the "acknowledged father of the cozy murder mystery"
Poetry:The Ballad of the White Horse
His Ballad of the White Horse is one of the last epic poems in the English language, and was admired by John Galsworthy, W.H. Auden, C.S. Lewis, J.R.R. Tolkien, Graham Greene, H.L. Mencken, and others (though Tolkien was later critical of its undoubted flaws).
(Chesterton wrote shorter poems as well, including comic ones)
Newspaper articles:
A newspaper article he wrote (he wrote over 4,000) is what first inspired Gandhi to start his movement to end British colonial rule in India
Literary criticism:Charles Dickens
His biography Charles Dickens helped spark a revival in Dicken's work, and was considered by many people the best book ever written on Dickens (for instance, by Theodore Roosevelt, George Bernard Shaw, T.S. Eliot, etc.). And Dicken's own daughter informed Chesterton of how much she liked the book.
Social criticism:Eugenics and Other Evils; What's Wrong With the World
Chesterton's 1922 book Eugenics and Other Evils made Chesterton one of the very few major writers to speak out against eugenics in the early part of the twentieth century.
And, commenting on his book What's Wrong With the World, Michael Crichton wrote:
Chesterton lost the debate about the future direction of society to his contemporaries H. G. Wells, Bertrand Russell, and George Bernard Shaw. Chesterton saw the implications of their vision of twentieth century society, and he predicted exactly what would come of it.
Christian apologetics:
C.S. Lewis credited Chesterton's book The Everlasting Man to have been the most important contemporary book in his conversion from atheism to Christianity, and referred to it as the very "best popular defense of the full Christian position" he knew of.
Economics:The Outline of Sanity
Chesterton's leadership in the distributist movement was also influential. For instance, E.F. Schumacher's book Small is Beautiful grew out of an essay which he originally named "Chestertonian Economics".
no subject
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As for Chesterton, er, well, it depends on what you are interested in. He basically wrote in all genres (or so it seems) on every topic. He was one of the most prolific writers ever (with over fifteen million words in print). To give a few examples of his work and their influence, which I document (for the most part) on my list of Chesterton's influence (http://augustine.livejournal.com/7853.html#cutid1), let me note the following, giving only one sample from each category, just to see what you might be interested in. From there, I can give you more detail on any individual category (and I'm missing some categories, no doubt).
Novels: The Man Who Was Thursday
Terry Pratchett and Neil Gaiman dedicated their novel Good Omens to Chesterton because, according to Gaiman, they felt that while writing Good Omens they were, on a very fundamental level, "doing The Man Who Was Thursday".
Short stores: Father Brown detective stories.
Strand Magazine describes Chesterton as the "acknowledged father of the cozy murder mystery"
Poetry: The Ballad of the White Horse
His Ballad of the White Horse is one of the last epic poems in the English language, and was admired by John Galsworthy, W.H. Auden, C.S. Lewis, J.R.R. Tolkien, Graham Greene, H.L. Mencken, and others (though Tolkien was later critical of its undoubted flaws).
(Chesterton wrote shorter poems as well, including comic ones)
Newspaper articles:
A newspaper article he wrote (he wrote over 4,000) is what first inspired Gandhi to start his movement to end British colonial rule in India
Literary criticism: Charles Dickens
His biography Charles Dickens helped spark a revival in Dicken's work, and was considered by many people the best book ever written on Dickens (for instance, by Theodore Roosevelt, George Bernard Shaw, T.S. Eliot, etc.). And Dicken's own daughter informed Chesterton of how much she liked the book.
Social criticism: Eugenics and Other Evils; What's Wrong With the World
Chesterton's 1922 book Eugenics and Other Evils made Chesterton one of the very few major writers to speak out against eugenics in the early part of the twentieth century.
And, commenting on his book What's Wrong With the World, Michael Crichton wrote:
Chesterton lost the debate about the future direction of society to his contemporaries H. G. Wells, Bertrand Russell, and George Bernard Shaw. Chesterton saw the implications of their vision of twentieth century society, and he predicted exactly what would come of it.
Christian apologetics:
C.S. Lewis credited Chesterton's book The Everlasting Man to have been the most important contemporary book in his conversion from atheism to Christianity, and referred to it as the very "best popular defense of the full Christian position" he knew of.
Economics: The Outline of Sanity
Chesterton's leadership in the distributist movement was also influential. For instance, E.F. Schumacher's book Small is Beautiful grew out of an essay which he originally named "Chestertonian Economics".
(continued in another comment)