The 'Very Legal and Very Cool' meme originated from a December 2018 tweet by Donald Trump, who used the phrase to defend his business discussions regarding a potential project in Moscow. The internet immediately latched onto the defensive and repetitive phrasing, transforming it into a sarcastic catchphrase for anything that is obviously suspicious, ethically dubious, or hilariously incompetent. Users typically apply the text to situations where someone is trying too hard to normalize an abnormal action or clear their name. Its longevity stems from its versatility in political commentary, corporate satire, and everyday awkward social interactions.