(5) James Joyce
Joyce's mastery of language and inventiveness with new literary forms made him possibly the most critically acclaimed and influential novelist of the 20th century. Ulysses, Finnegans Wake, Dubliners, and A Portrait of the Artist as a Young Man are all firmly entrenched in the modern canon, and although his wildly experimental tendencies make reading his work tedious, it's tough to deny that Joyce had a pretty firm grasp of human nature.
(12) Bill Simmons
Simmons, better known as ESPN's Sports Guy, changed the sports journalism game earlier this decade by foregoing all of the field's tired conventions and giving fans what they really wanted: something written from their point of view. By eschewing locker rooms and insider access, Simmons was able to inject a new sensibility into sports writing, one that used a relentlessly playful and sarcastic tone, myriad references to 80's movies, unapologetic Boston homer-ism, and Simmons' always-sharp sense of humor in lieu of banal postgame quotes from players. It worked. The Sports Guy's columns became required reading for sports fans, while everyone else's writing started to feel a little bland by comparison.
Both writers have a tendency to write incredibly long works. Both writers' outputs show a willingness to break with convention and test the limits of what their form can do. Both writers loved to mock Isiah Thomas' decision making with the Knicks. (At least we think that's what Joyce was doing in the Penelope episode of Ulysses.) As of yet, Simmons hasn't written anything quite as long as Ulysses, but his long-awaited forthcoming NBA book may in fact be 783 pages long. This one's a tough call.
[See the whole bracket here.]