Bart Simpson is one of the coolest characters in television history due to his iconic, anti-authoritarian attitude and timeless style.
Here is what makes Bart so cool:
Skateboarding Icon: Bart practically invented the phrase "eat my shorts" while riding his board down

Evergreen Terrace. His casual, effortless mastery of the half-pipe solidified his cool factor from the very first short.

Catchphrases: From "Cowabunga!" to "Don't have a cow, man," his unique vocabulary instantly became part of the global pop-culture lexicon, proving he sets trends wherever he goes.

Street Style: His classic outfit—orange t-shirt, blue shorts, and blue sneakers—is simple yet instantly recognizable and has influenced street fashion for decades.

Rebellious Spirit: Bart embodied the quintessential '90s slacker cool: smart enough to know the rules, but too cool to follow them. He constantly challenges authority, whether it’s Principal Skinner, Mr. Burns, or even his own father, all with a cheeky grin.

Mischievous Pranks: His elaborate pranks, especially the frequent prank calls to Moe's Tavern, show a quick wit and a cunning streak that are both hilarious and undeniably clever.