Discounting Otis, the beloved town drunk from "The Andy Griffith Show," and Robert Downey, Jr. , we'll go with Henry Earl
According to Wikipedia, Earl has been arrested, as of January 2007, 937 times. A Newsweek article and interview with the habitual offender reports he's been "homeless and unemployed since 1969" and "spends just about every other night in jail ... mostly for public drunkenness."
Earl became an Internet star when his county jail's web site
began showing the incarceration status of past and present offenders, not to mention years of mug shots
. Earl's notoriety led to a spot on the "Jimmy Kimmel Show," and later spawned a rock song, a Firefox browser extension, and an oil painting, among other tributes.
If you want to keep apprised of Earl's comings and goings, this site is a pretty good bet.