Jon Stewart is famous for a lot of things after 16 years on Comedy Central’s “The Daily Show,” but one legacy will certainly be — his takedowns. It quickly became clear after Stewart took over as host: You didn’t want to be on his bad side.

However, as scathing as Stewart could be, he also had some people he genuinely enjoyed: Here’s a look back at some of his well-known friends, enemies and frenemies through the years.

[Jon Stewart confirms final guests for his last week on ‘The Daily Show’]

FRIENDS

* Stephen Colbert

These BFFs bonded long ago when Colbert was a “Daily Show” correspondent — Stewart was giddy whenever his pal took a break from “The Colbert Report” to stop by. And Stewart seems thrilled to watch his friend thrive and land his next job. “There’s no greater joy than seeing a genuinely good man who works as hard as he can every day and deserves all the success in the world actually get that success,” Stewart said when CBS announced that Colbert would take over for David Letterman.


* Brian Williams

As the Huffington Post wrote (when wondering how Stewart would cover the story of the embattled NBC News anchor this past winter), “Williams and Stewart have, over the course of many interviews, developed something of a collegial relationship — if not an outright bromance.” Williams was a frequent “Daily Show” guest, and Stewart was one of the first people to appear on Williams’s ill-fated “Rock Center.”


* President Obama

They did have those White House meetings! But really, Stewart always enjoyed it when Obama stopped by the show, dating back to his first appearance in 2005.


* Malala Yousafzai

The teenage Nobel Peace Prize winner and education advocate rendered Stewart speechless the first time she stopped by at age 16. “I know your father is backstage, and he’s very proud of you, but would he be mad if I adopted you?” Stewart asked her.


* Denis Leary/Louis C.K./Colin Quinn

This is straight from Stewart: Asked recently about his favorite guests, he rattled off these three, because they’re his pals. Those interviews don’t even qualify as work, he says.


ENEMIES:

* Jim Cramer

One of Stewart’s most famous takedowns after the 2008 economic crisis, was when Stewart devoted multiple shows to calling out CNBC for irresponsible financial reporting. Later, Jim Cramer appeared on his show for a highly touted smackdown. “I understand you want to make finance entertaining, but it’s not a f—ing game,” Stewart told him.

* Sean Hannity/Glenn Beck/Fox News

How do you even count the number of times that Stewart has skewered Fox News? It might actually be impossible. For just one example, Stewart recently challenged Fox News to a “lie off” after Megyn Kelly said a lot of Stewart’s “attacks that were levied on me had no foothold in the facts.”

“Your distortions and lack of fact footholds against mine!” Stewart said, adding that he compiled 50 of the network’s lies in one six-second Vine clip.


* “Crossfire”

Stewart always thought CNN’s show was bad, but as he clarified to hosts Tucker Carlson and Paul Begala when he stopped by in October 2004, “It’s not so much that it’s bad as it’s hurting America.” He called the show painful to watch, accusing them of partisan hackery. “You have a responsibility to the public discourse, and you fail miserably,” he said. When Carlson and Begala shot back that “The Daily Show” could use work, too, Stewart uttered his now-famous zinger: “You’re on CNN! The show that leads into me is puppets making crank phone calls. What is wrong with you?”


* Rick Sanchez

Stewart made fun of CNN’s Rick Sanchez for years. Sanchez lashed out in response on a radio show, calling Stewart a “bigot” and mocking the idea that Jewish people could be a minority when “everybody who runs CNN is a lot like Stewart.” He was fired by CNN a day later.


* Judy Miller

Stewart reached peak anger level when former New York Times reporter Judy Smith came on the show to talk about her new book, and he took her to task for reporting on Saddam Hussein’s weapons of mass destruction. “I believe that you helped the administration take us to the most devastating mistake in foreign policy that we’ve made in 100 years,” Stewart said, though he added that she seemed like a “lovely” person.


FRENEMIES:

* Bill O’Reilly

These guys. Through opposite sides of the spectrum, many arguments, and the “Rumble in the Air-Conditioned Auditorium,” each talk show host has genuine respect for the other.


* Seth MacFarlane

After the “Family Guy” creator publicly criticized Stewart for continuing his show during the Hollywood writers’ strike, Stewart called MacFarlane and “ripped” him for an hour. MacFarlane later recounted the details and seemed a bit shell-shocked from the incident. But he’s been on Stewart’s show several times since, so all seems okay.

 

Read more: 

— Can we go on without Jon Stewart? Of course we can. He’s shown us how.

– Jon Stewart: Meeting with Obama wasn’t a secret

– Many millennials are about to lose their most-trusted news source: Jon Stewart

– Jon Stewart’s progressive legacy