#500MoviesIn500Days was an attempt to enter the Guinness Book of World Records by frequent On Cinema guest Gregg Turkington. Announced during S03E05, Turkington planned to watch 500 movies within a 500 day time span, starting with the film Jack Frost on July 30, 2013, along with one other movie. Crucially, Turkington's challenge did not require him to watch a movie every day, so long as he watched more than one movie on other days. In this way, a backlog could be built up in case Turkington had to miss a day due to unforeseen circumstances.

Turkington's focus of movies to watch were films currently playing in theaters, and movies in his collection he had not previously seen.^[1]

By day 15, Turkington had watched 19 movies, giving him a surplus of 4.^[2]

Due to an unforeseeable setback on the 500th night, Turkington was unable to view the 500th film that day. The project was revamped into #501MoviesIn501Days, setting an even more impressive record on day 501.