The fifth season of On Cinema at the Cinema began airing July 2, 2014.

Tim takes up residence in Jackson Hole, Wyoming, and shuttles back and forth between there and Los Angeles on his new Kawasaki motorcycle. He opens a publishing company, and makes plans for his debut book, Hog Shots, as well as a deal with Gregg for a book of film essays. Regarding the revelation of Ayaka's pregnancy at the end of last season, Tim sends her funds to undergo an abortion. He is also temporarily blinded in an incident involving his motorcycle, and sports a black eye for much of the season.

The first season of Decker premieres, between episodes 3 and 4. There is a bit of initial friction between Tim and Gregg after Tim uses some footage of Gregg without permission, but Gregg warms to the show, and expresses a desire to be a part of the show moving forward. The first season wraps after five episodes.

Gregg is forced to start his 500 Movies in 500 Days campaign over from scratch, as his list of watched films was lost. However, he finds his original list by the season finale, allowing him to add the two and jump forward significantly. At season's end, he sits at 327 films.

In the season finale, it is revealed that Ayaka did not go through with the abortion, and gave birth to a son, whom she named Tom Cruise Heidecker Jr. She uses the funds Tim sent to return to the United States and raise the boy with Tim.