Jon Stewart’s decision to leave his Comedy Central show brings an end to more than a decade of contentious interviews with politicians and news anchors, pointing out the absurdities of politics in a way few others could.
Here are Stewart’s top moments skewering politicians and the U.S. political system:
The aftermath of 2000’s presidential election between George W. Bush and Al Gore turned Stewart, who’d just started the show, and a cast of supporting characters that included Stephen Colbert and Steve Carrell, into must-watch television.
READ: How Jon Stewart changed politics
When Bush said that he “was not elected to serve one party,” Stewart quipped: “You were not elected.”
Stewart’s recurring series blasts the U.S. military’s prison in Cuba, as well as President Barack Obama’s failure to accomplish his 2008 campaign goal of shuttering it.
READ: Who will Comedy Central pick to replace Stewart?
In one skit, he dressed an Elmo puppet up and called it “Gitmo,” and used the puppet to highlight an NBC News report about the comforts afforded to prisoners detained in the facility.
“Gitmo bleed America dry from prison. Paying to take care of Gitmo and friends – death by 1,000 cuts. Gitmo bankrupt America!” Stewart, playing Gitmo, said.
Battles with Bill O’Reilly
The Fox News anchor was a frequent target of Stewart’s criticism, and over the years the two occasionally appeared on each others’ show, in a sign of mutual respect.
Ahead of one of Stewart’s appearances on O’Reilly’s show, O’Reilly introduced his guest by simply saying: “Stewart is back. It’s inexplicable, but he’s here.”
Stewart responded, during O’Reilly’s next appearance on his show, by having the Fox News host serenaded, with rose petals thrown in front of his feet as he walked onto the set.
Nancy Pelosi and corruption
When top House Democrat Nancy Pelosi visited his set, Stewart left her stammering with a series of questions about the corrupting influence of money in politics – and the behind-the-scenes access that money buys.
When Pelosi pointed to Republicans taking energy money, Stewart said Democrats complicated financial regulatory reform in part because they take Wall Street money.
“The important stuff that’s happening is what’s happening behind closed doors,” Stewart said.
Mike Huckabee and gay marriage
In the wake of the 2008 presidential election, former Arkansas Gov. Mike Huckabee, a social conservative, tried to defend his opposition to same-sex marriage against Stewart, who compared Huckabee’s stance to segregation.
“I think it’s the difference between what you believe gay people are and what I do,” Stewart said. “Religion is far more of a choice than homosexuality, and the protections that we have for religion – we protect religion, and talk about a lifestyle choice, that is absolutely a choice. Gay people don’t choose to be gay.”
As Huckabee argued that the definition of marriage has stood for thousands of years, Stewart said: “It feels like semantics is cold comfort when it comes to humanity.”