I’ve been watching The Simpsons since the early 90’s when I was roughly Bart’s age. That manic force of the character’s anarchistic energy was appealing to the younger me for a litany of reasons. The uncontrolled ID, a character who was cool, but still had clear antagonists to his story. Yet in the end, this behavior is unquestionably self destructive. In the numerous Simpsons future episodes Bart’s future is never truly desirable. But the Future of Milhouse is open to many possibilities. He may work in the White House, or become a massive Hulk, or even marry Lisa. In any event he is a far more active participant in his own future. Bart is just going to coast on his natural charm, as a cliched 90’s slacker. Just like Milhouse growing up I wanted to be Bart, but eventually I grew up and when Bart did he got an apartment with Ralph. A room mate who eventually dumps him.
Despite the overall first impressions and numerous self esteem issues, Milhouse is cooler than Bart. Aside from El Barto, he is constantly getting nailed for the pranks he pulls. Milhouse got to be Fallout Boy, Milhouse had a girlfriend before Bart, and Bart’s first girlfriend Jessica Lovejoy is clearly abusive. Samantha Stanky however just wants to kiss in a tree fort. While both Bart and Milhouse have less than desirable family lives, Milhouse is indicated to be in therapy to help him adjust, and he does.
Despite being clearly nerdy, Milhouse is not the passive creature that Bart is. While Bart is content to fight authority for reasons he truly does not understand. Milhouse wants more, and is shown to be more capable than Bart. Such as when Milhouse moves to Capital City in “Milhouse Doesn’t live Here Anymore.” Milhouse is able to totally re-inent himself in a cooler image. Contrast this to Bart’s failures at Cypress Creek when the family moves in, “You Only Move Twice.” Bart is placed in a remedial class where he can’t even engage in mischief. This is after the other kids were initially so enamored with him. I was like them once, but now everything is coming up Milhouse.