My general feeling is that gawker wins and rickdugan is close. But max_starr has a good entry with the stripper boyfriend who tried to do a drive by on a bicycle!
In my opinion, to qualify as a truly brilliant crazy story the crazy story has to be plausible (even if it is unlikely), crazy, possibly stupid (OK, probably stupid), and possibly dangerous. Ideally costly to the poster and even dangerous to the poster (perhaps those things go along with crazy).
So juicebox69's stories about covering himself in bacon and lying down for strippers and/or dachshunds don't qualify on the plausibility scale, though who knows? Of course, those stories are mostly told by others and not by juicebox69!
JohnSmith69's stories about DS's are also entertaining and plausible, but typically not dangerous or stupid! Not that there is anything wrong with that, in fact my hat is off to JohnSmith69 for not indulging in the stupid and dangerous!
max_starr's story about meeting the criminal boyfriend when he was passed out and the stripper saying stuff about them fighting probably qualifies under stupid and dangerous. So overall he's giving gawker and rickdugan a run for their money!

So now it’s your turn to entertain us, if you don’t have any real crazy ones make one up ! ;)