The phrase “How do you like them apples?” (or “How you like them apples?”) likely originates from American slang in the early 20th century, though its exact origin is debated. It generally conveys a sense of triumph, challenge, or one-upmanship.

Possible Origins:

1. World War I Artillery Slang (1910s) - British and American soldiers referred to certain types of grenades or artillery shells as “toffee apples” due to their round shape. When launching an attack, soldiers might have used a phrase like “How do you like them apples?” as a taunt to the enemy.
2. Early American Slang (1920s-1930s) - The phrase started appearing in American slang as a way to rub in a victory or deliver a rhetorical punch. It was likely a variation of similar expressions that emphasized irony or a reversal of fortune.
3. Popularization in Mid-20th Century - The phrase appeared in various pulp fiction, movies, and comics in the mid-20th century, often used by tough or streetwise characters.
4. Modern Recognition: Good Will Hunting (1997) - The phrase was famously used in Good Will Hunting when Matt Damon’s character, after outsmarting a Harvard student, slaps a phone number on a diner window and says, “How do you like them apples?” cementing its place in pop culture.

While the exact origin remains uncertain, it’s clear that the phrase has evolved into a way of expressing victory, unexpected success, or a dramatic comeback.

From ChatGPT.