Corey Duffels Big Brother interview didn't end but surely impacted his career.
Billy Pepper punching Phelps and getting banned from Thrasher
That one gay skater who was brave enough to come out in the 90s (forgot his name, sorry) and lost his sponsors.
Earl Parkers, (the "master journalist") rise and fall within a year or so
Edit: missed the "hilarious" in the title of the post but I will keep it up anyway. None of these are hilarious.