The Brief: This meme format uses a still from Django Unchained of Leonardo DiCaprio laughing as a reaction image.

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These Leonardo DiCaprio laughing memes come from a scene in Quentin Tarantino’s 2012 film Django Unchained featuring a still of Dicaprio’s character, Calvin Candie, holding a drink and laughing. Variations of image macro memes featuring Calvin, the film’s main antagonist have been circulating online for years. In early August 2020, this particular format became popular on Reddit and Instagram.
https://www.instagram.com/p/CDg4EAtAPkJ/?utm_source=ig_web_copy_link
Leo’s expression in this image appears as if he’s laughing hard. Some iterations of these memes suggest that he’s laughing at an immature joke or a Dad Joke. Others imply that he’s laughing due to schadenfreude, which is fitting for the character.
This format is also reminiscent of another well-known DiCaprio meme: the one from The Great Gatsby where he’s holding his drink up for a toast.
And insisting you can pause you’re online game. from dankmemes
Another usage of the Leonardo DiCaprio laughing format: