Jon Stewart's style as "Daily Show" host has morphed from deadpan sarcasm to informed, dynamic pugnaciousness. Since his debut in 1999, Stewart has in many ways single-handedly transformed what we expect of news satire. The show has become a forum for direct interrogations with political figures and comprehensive appraisals of the media. It's fair to say his influence has only just begun.

Perhaps most impressively, Stewart has been responsible for giving us smart, swift interviews with towering figures. Here's how Emmy-winning comic handled his eight biggest, most important, and most noteworthy interviews. 

  • Hillary Clinton, 2014: Turning intense media speculation into a hilarious game
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    During the seemingly endless period of time when Hillary Clinton hadn’t acknowledged she’d be running for president in 2016, Jon Stewart had fun with the former Secretary of State by asking her vague questions about the presidency. “Do you want to sit in traffic or cause it?"
  • Barack Obama, 2015: Aggressive questioning peppered with respect
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    The president has appeared numerous times on “The Daily Show,” but I think his richest moment was his most recent visit when Jon asked about his “senioritis” and how he felt about his efficacy in office. Their rapport is sharp, and Stewart keeps Obama relatively candid using direct questions and even quicker moments of drollness.
  • John McCain, 2008: Asking (and insisting) about his running mate
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    During John McCain’s campaign trail appearance on “The Daily Show,” Stewart surprised the Arizona senator with a bold question: Why don’t you pick Hillary Clinton as a running mate? McCain responded that he hadn’t considered it, but the query sent a wave of awe through the audience. Wonder if he regrets not taking him up on that offer now.
  • Jim Cramer, 2009: Nailing an interviewee to the wall, even when he is begging to be let down
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    One of the stranger “Daily Show” appearances is CNBC personality Jim Cramer’s. Stewart hammered him for his ballistic onscreen presence, and Cramer… couldn’t really respond to anything? Every Stewart snipe seemed to catch him off guard, and Cramer barely came up with a cogent counterargument for anything lobbed at him. Stewart never eased up. His even-handed evisceration lasted for 22 minutes and Cramer’s apologetic sputtering seemed to go on for hours beyond that.
  • Malala Yousafzai, 2013: Leveling with an extraordinary adolescent through philosophy
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    Though Malala Yousafzai, the teenager who fought in her native Pakistan for educational rights, survived the Taliban’s attempted murder, and became the world’s youngest Nobel Peace Prize recipient, is certainly worthy of an interview. The question is, how does one properly interview a teenage advocate? Wisely, Stewart leaves much of the talking to Yousafzai but begins with a smart, simple question: How do you feel about humanity?
  • Bill O'Reilly, 2015: Picking exactly one topic
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    Bill O’Reilly has visited Jon Stewart’s show a number of times (and vice versa), and that means Jon Stewart has found an answer to a difficult question: How do you have a reasonable, watchable conversation with someone whose views are (and will remain) diametrically opposed to yours? In the case of the clip above, Jon Stewart picked a single topic — white privilege — and debated the concept with O’Reilly for a full 12 minutes. It’s such an organic conversation that you forget it’s just another book plug.
  • Ralph Nader, 2000: Getting serious with the candidate no one takes seriously
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    In his early days on “The Daily Show,” Stewart named his interview with Ralph Nader as one of the brighter talks on the show. The clip from 2000 is one of the first signs of what “The Daily Show” would become; Stewart asks about Nader’s exclusion from national debates, opinions on Bush and Gore, and why he attempts political stature at all. It’s one of the first examples of Stewart blending interrogative wryness with political insight, and it’s also one of his first great moments as an interviewer.
  • Kurt Vonnegut, 2005: Letting an elusive legend speak
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    Kurt Vonnegut appeared on “The Daily Show” about two years from his death, and his stint in Jon’s chair was marked by political speechifying, jokes about evolution, and that otherworldly presence. Stewart seemed to be analyzing his aura right along with us, and he gave the legendary author room to be as droll, theatrical, or proclamatory as he preferred.