The 'Leo is all of this legal' meme originates from the 2013 film "The Wolf of Wall Street," directed by Martin Scorsese and starring Leonardo DiCaprio as Jordan Belfort. This particular scene captures DiCaprio's character with a smirk, delivering the iconic line, "Is all of this legal? Absolutely fucking not." The film is a satirical look at Wall Street excess and corruption, and this scene embodies the audacity and flagrant rule-breaking of its protagonist. It has become a popular meme format because of its perfect encapsulation of shamelessly flouting the rules with an air of smug self-awareness.