In many ways, the political landscape of 1999 was different than it is today. Bill Clinton was racing towards the end of his second term. Flash-forward 16 years later and his wife, Hillary, is the front-runner in the Democratic race to succeed President Obama. It was a pre-9/11 America, a country readily excited for the new millennium, and vastly unprepared for the tragic 2001 terror attacks that would forever change the way we view national security. Despite all this, though, as is always the case in politics, it was more of the same.

Perhaps no other show on television has personified that brutal realization the last 16 years than The Daily Show with Jon Stewart. Stewart and his colleagues have torn apart politicians and pundits for nearly two decades, all the while becoming the unexpected voice of a generation. It's a title the late night host has shot down on numerous occasions--he'd rather be a satirist than a journalist--but the fact of the matter is that Stewart is a beacon for honest news to many young (and old) viewers.
So when it comes to talking about Stewart's legacy, how are we to talk about it? Is he a comedian merely poking fun at the 24-hour news cycle? Or is he something more? Whatever Stewart ends up being hailed as by his colleagues and by the think pieces and even by his enemies when all of this is over remains to be seen. One thing is for certain, though: Jon Stewart stopped giving a shit when he announced his retirement from the show. And it’s amazing.

If you look at Stewart’s final weeks hosting The Daily Show, there’s a certain feeling of relief throughout. In an interview with The Guardian after announcing he’d be leaving the show this year, Stewart blamed a level of dissatisfaction, like a car you’ve driven for years that’s just not the same as it once was. “

“It’s not like I thought the show wasn’t working any more, or that I didn’t know how to do it. It was more, ‘Yup, it’s working. But I’m not getting the same satisfaction,’” he says. “These things are cyclical. You have moments of dissatisfaction, and then you come out of it and it’s OK. But the cycles become longer and maybe more entrenched, and that’s when you realize, ‘OK, I’m on the back side of it now.’”

The car is getting him places, but the check engine light has been on way too long…and yet, he’s never been better.

Yes, Stewart seems relieved that this feeling of dissatisfaction will be gone soon. But it’s only fueling him to deliver some of his best material. In these final weeks, Stewart has been unapologetic in his…satire? It’s bold to call it that at this point. The host is leaving no stones left unturned, and it seems like his comedy is more brutal truth than parody. One might even call it journalism.

How far has Stewart’s level of no-fucks-given really gone? Well for starters, he did an entire segment using only noises and hand gestures rather than talking just because he’s always wanted to. He reigned down a verbal assault like none other on Fox News on Monday’s episode, stating “Adios mother fuckers” before realizing he still had three more shows left.

And while all of this sounds like the antics of a man who doesn’t care anymore, it’s only because he no longer cares who he cuts ties with. Come Thursday night, Stewart’s 16 year old run will be over. He won’t be interviewing the very conservatives (or liberals) he’s berated all these years. He doesn’t have to care anymore. He can do whatever he wants. But what he still does care about is what matters.

After the tragic South Carolina attack, an emotional Stewart began the following night’s show with no prepared segment. He merely spoke to his audience. It was no laughing matter, and indeed, nobody was laughing. He labeled the attack as terrorism, something the main news sources had largely been failing to do at the time. At the end of the day, Stewart will always care about the issues that matter and how we as a society perceive them.

With his curtain call approaching, Stewart’s legacy is firmly in the hands of his audience. And while Fox News may be jumping for joy that he’ll be gone, he’ll probably rest easy at night. Not only because he no longer has to deal with this dissatisfaction, but because he went out satisfying everyone else.