This question is intentionally vague: What’s the greatest double-feature of all time?
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There Will Be Blood & No Country For Old Men go perfectly together! Two masterpieces of the 21st century. That is a long time to be sitting - I normally don’t watch movies back-to-back either, unless I’m making a special effort at it. In the right circumstances it’s a ton of fun.
They hit wide release within a couple months of each other. After some deliberation I've arrived at my final answer: The Straight Story (1999) followed by Bad Grandpa (2013)