8 moments of snarky satire and heartfelt patriotism from Jon Stewart

After 17 years hosting The Daily Show, an emotional Jon Stewart announced yesterday he will be stepping down.

Stewart joined the satirical news program in 1999, hosting a somewhat dry recap of the day’s most outrageous news. In the months after the 2000 election, however, the show found its footing and eventually became a vehicle for some of sharpest political satire of the decade — coverage that won The Daily Show its first Peabody Award.

Between goofier segments, Stewart posed serious questions that many journalists didn’t ask in the aftermath of 9/11 and the invasion of Iraq. Meant originally as smart entertainment, the show evolved to have a harder edge, and young people around the country began to cite the show as their main source of news.

As Daily Show fans get ready to say goodbye, take a look at 8 quintessential Jon Stewart clips, listed below in chronological order.

1. When he reported the Supreme Court’s decision on the 2000 election.

Stewart takes on the tenor of a traditional news anchor to call the end of the disputed 2000 election, joking that George W. Bush won “100 percent of the African-American vote” in the Supreme Court.

2. When his heartfelt speech after 9/11 reminded a shaken nation that there were still reasons to laugh.

Stewart offers a special moment of solemnity for a show whose bread and butter has been bombastic jabs at those in power.

3. When he took on Crossfire’s hosts while appearing as a guest on their own show.

In this infamous clip, shared over 8 million times, he lambasted Crossfire for not contributing to intelligent public debate and for participating in partisan bickering. The show was canceled three months later, when CNN’s CEO, Jonathan Klein, indicated he sympathized with Stewart’s criticism and wanted to change the tone of the network’s shows.

4. When he used Sesame Street to illustrate problems at Guantanamo.

Gitmo, an Elmo puppet masquerading as a Guantanamo detainee, became a “senior imprisoned correspondent” on the show. The segment turned into a semi-regular attack on the Obama administration for not upholding campaign promises to shut down the prison.

5. When he exposed Congress’ reluctance to provide health care benefits for 9/11 first responders.

Stewart recalls numerous instances of politicians using the 9/11 attacks for political rhetoric.

6. When he took a hard look at America’s reaction to the Arab Spring.

Watch Stewart and former Daily Show staffer John Oliver dig into the country’s reaction to falling regimes from Libya to Egypt.

7. When he held the Obama administration accountable for the bureaucratic mess standing in the way of veterans receiving benefits.

Stewart urged President Obama to apply the same logic and efficiency that got him elected to the issue.

8. When he compiled CNN’s far-ranging coverage of the disappearance of Malaysia Airlines Flight 370.

Stewart dives into the sometimes absurd lengths CNN went to keep viewers tuned in, including considering whether a black hole may have been responsible for the disappearance of the flight, a segment Columbia Journalism Review included its list of the worst journalism of 2014.