With It

My brother was commenting over dinner last night that we didn't used to really hang out when we were younger. I responded to him that the age gap between us was a bigger deal when we were younger, but now he's more "with it" and almost an adult. He then asked what "it" was and proceeded to quote Grandpa Simpson, which I thought was pretty funny:

"I used to be with 'it.' But then they changed what 'it' was. Now, what I'm with isn't 'it,' and what's 'it' seems weird and scary to me."

From way back: