Lollerskates is a classic internet slang term that emerged in the early 2000s as a more intense version of LOL. Combining LOL with roller skates, the term was often paired with phrases like 'I'm on my lollerskates' to indicate that something was extremely funny. It gained traction alongside other vehicle-based humor like the Roflcopter and Lmao-zine. While it originated in chat rooms and forums like 4chan and Something Awful, it became a staple of early image macro culture. Today, the meme is used to evoke nostalgia for the early web or to react to something absurdly hilarious with a vintage flair.