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Jon Stewart told viewers on Tuesday that later this year he’d be leaving his long-time role as host of The Daily Show. Here are five of his top moments:

Stewart’s first broadcast post-9/11 – Sept. 20, 2001

Along with the other New York-based talk-show hosts – David Letterman, Conan O’Brien, et al – Stewart had the difficult task of easing viewers back to reality following one of the darkest days in U.S. history. In a tearful, yet composed, opening segment running nearly nine minutes, Stewart said, “The view from my apartment was the World Trade Center, and now it’s gone.” In retrospect, what stands out most in the clip is Stewart’s unwavering sense of honesty and uncertainty in the face of an uncertain future. “Our show has changed, I don’t doubt that,” he said. “What it has become, I don’t know.”

Barack Obama makes his first visit – Oct. 26, 2010

In his first appearance on The Daily Show, the U.S. President defended his record and reiterated that he never promised transformational change would take place overnight. Stewart countered by suggesting that the Democratic Party had traded boldness for pragmatism, and told the commander-in-chief, “You ran on very high rhetoric, hope and change, and the Democrats this year seem to be running on, ‘Please baby, just one more chance.’ ” Undaunted, Obama returned to the Daily Show three more times.

Stewart vs. Bill O’Reilly on The O’Reilly Factor – May 16, 2011

Technically, The Daily Show host was a guest on the Fox News program The O’Reilly Factor – hosted by his longtime right-wing nemesis Bill O’Reilly – but Stewart owned the conversation. On this occasion, O’Reilly railed against the rapper/actor Common being invited to the White House, primarily because he wrote a song in support of Assata Shakur, who was convicted of killing a New Jersey State trooper. In his patently informed manner, Stewart clarified the facts and pointed out to O’Reilly that Common, along with Bono, Bob Dylan and other artists, had the right to creative expression. The sharp Stewart coda: “Why are you drawing the line at Common? There is a selective outrage machine here at Fox that pettyfogs only when it suits the narrative that suits them.”

Stewart does the Harlem Shake – Feb. 19, 2013

Nobody can ever say that Stewart doesn’t know how to have a good time. In recognition of the freakish appeal of the dance-cum-meme known as The Harlem Shake, the normally reserved host did his level best to replicate the trend’s frenetic movements, which he performed while wearing a safety helmet and surrounded by the expansive Daily Show production staff. As per Harlem Shake tradition, Stewart was eventually ditched by his co-workers and left dancing with himself. The best part: Stewart’s bold attempt inspired his friend and ex-colleague Stephen Colbert to mount his own Harlem Shake remix on The Colbert Report.

Stewart addresses the Charlie Hebdo tragedy – Jan. 7, 2015

Once again, Stewart was the voice of reason in the wake of a horrific tragedy – in this case, the murder of 11 people at the French satirical publication Charlie Hebdo in Paris by terrorists. Stewart opened that night’s show with sincere condolences for the magazine’s staff and families, and saying, “I know very few people go into comedy as an act of courage. Mainly because it shouldn’t have to be that.” And as he’s done so many times, Stewart wrapped by reminding viewers that for all the flaws of American society, the right to free speech is still a blessing. “However frustrating and outraged the back and forth can become, it’s still back and forth, a conversation among those on, let’s call it, team civilization,” he said. “And this type of violence only clarifies that reality.”