The Daily Show

"When we were developing the show, we wanted to reveal, as they did in Broadcast News with William Hurt and Ted Baxter [on The Mary Tyler Moore Show] that these people, these [news anchors], are merely shells of the people who work really hard and give them the info behind the scenes."

The host of the show, Craig Kilborn, was a pretty boy from Minnesota, by way of ESPN. One of the original correspondents, Beth Littleford, remembers him as being "dumb as wood." Which might explain why Kilborn thought it was a good idea to piss off one of the show's executive producers during an Esquire interview:

"There are a lot of bitches on the staff, and, hey, they're emotional people. You can print that! You know how women are—they overreact. It's not really a big deal. And to be honest, Lizz does find me very attractive. If I wanted her to blow me, she would."

Years later, Beth Littleford would respond in an interview with the Toronto Sun: "NO one would give the man a blowjob! NO one who was in their right mind who was not on drugs or under coercion would give the man a blowjob! That's my opinion."

A little more than a year after the Esquire debacle, smarmy Craig Kilborn was replaced by the lovable Jon Stewart. And somehow, over the years, The Daily Show slowly transformed into an actual news show, gradually transforming itself bit-by-bit into the very thing it reviled.

Beginning in late 2002, the comedy program has been regularly visited by some of the nation's most powerful politicians:

Vice President Al Gore, Senator John McCain, Senator Joseph Lieberman, Senator Bob Kerrey, Senator Charles Schumer, Senator Arlen Specter, Representative Dick Gephardt, 2000 Green Party Presidential Nominee Ralph Nader, New York City Mayor Michael Bloomberg, former Senator and 1996 Republican Presidential Nominee Bob Dole, who also served as Guest Political Commentator for the series' "Indecision 2000" election coverage, Senator John Edwards, who formally announced his candidacy for the Democratic nomination for President of the United States on "The Daily Show" on September 15, and 2004 Democratic Presidential Candidate John Kerry.

Lizz Winstead touched on this in 2004 when she was interviewed for Mother Jones magazine:

REPORTER:	Speaking of The Daily Show, I'm always impressed by how comfortably Jon Stewart interviews Kissinger or even Richard Perle.
WINSTEAD:	Jon's tremendous. I feel, though, when you are interviewing a Richard Perle or a Kissinger, if you give them a pass, then you become what you are satirizing. You have a war criminal sitting on your couch—to just let him be a war criminal sitting on your couch means you are having to respect some kind of boundary.
	[...]
REPORTER:	So did that disappoint you, when Jon Stewart was nice to Kissinger?
WINSTEAD:	I don't mean that you would necessarily need to grill Kissinger. But to let it go...
REPORTER:	So you should jokingly say, "Say, Dr. Kissinger, what about those 2 million dead Cambodians...?"
WINSTEAD:	Exactly! As a way to say something. To me, it seems like the elephant in the room.

Timeline