The phrase 'That's Wiggity Wack, Yo' is famously associated with Poochie the Dog, a character introduced in a 1997 episode of The Simpsons titled 'The Itchy & Scratchy & Poochie Show.' Poochie was designed as a corporate caricature of 'extreme' 90s attitude, forced into a cartoon to boost ratings. The phrase has since become the definitive way to ironically express disappointment or to mock someone trying too hard to stay relevant. In meme culture, it serves as a nostalgic reaction image used when something is decidedly uncool, unfair, or simply frustrating, capturing the essence of forced coolness gone wrong.