DiCaprio-related memes cluster into a few overlapping strands. The longest-running was the 'Leo still hasn't won an Oscar' joke, which treated each Academy Awards ceremony as another chapter in a gag about how prolific he was without a statuette, an angle Urban Dictionary summed up as 'almost every movie he is in, is critically acclaimed' while noting he 'has never won an Oscar although many people say that he should have'6. Alongside that sat a growing bank of screenshot reactions pulled from his filmography, including the 'Cheers Leo' toast from The Great Gatsby and the pointing scene from Once Upon a Time in Hollywood4.

A second strand focused on his off-screen life. The 2016 photo of a Russian civil servant who looked identical to DiCaprio kicked off an ongoing 'Leo has a twin somewhere' bit2, while paparazzi shots of him with vape pens and yacht guests became their own image macro genre3. His decades-long presence in tabloids gave meme accounts a deep archive to pull from, keeping him in circulation long after the specific 2016 flashpoints faded4.

Most DiCaprio meme use follows one of two patterns. Reaction image use pairs a film still, typically the Gatsby toast, the Django laugh, or the Once Upon a Time in Hollywood point, with a caption describing a moment of recognition, agreement or smug satisfaction4. Running-joke use frames a new event as another entry in an ongoing DiCaprio narrative, whether that is the Oscar drought (before 2016) or his rumored preference for younger partners, often as a tweet reply or a quote-retweet with a screenshot of the source story6.