Adam Sandler – Netflix Deal (2014-Present)

In one of Netflix's early moves to gain legitimate Hollywood star power, they signed a four-picture deal with comedian Adam Sandler for a reported $250 million, or $62.5 million per film. Even though the quality of those films have been amongst his most critically reviled works, they've been popular enough on the streaming giant that Netflix has twice renewed the deal – first in 2017 and again in 2020. If those figures remain the same, that could be upwards of $750 million, although only the initial deal is confirmed.