Movie: Plan 9 from Outer Space (1959)
Any list of the "worst" anything in movies feels incomplete without the presence of Ed Wood, who's widely considered to be the worst filmmaker of all time. The funny thing is, though, that cinephiles have always held Wood warmly in their hearts, because, god bless the poor guy, he really believed in himself and made piss-poor flicks like Glen or Glenda and Plan 9 from Outer Space with the passion of a much better director.
In addition to possessing zero talent himself, Wood was also stricken by minuscule budgets, so when it came time to show a bunch of flying saucers hovering above a cityscape, he endearingly made a bunch of toy ships with do-it-yourself, kid-friendly kits and dangled them from cheap wires. Unfortunate, hopeless ingenuity at its finest.