21 of Jon Stewart’s best political interviews on ‘The Daily Show’

He skewered American politics for 16 years. Here are some of his best high-profile chats.


Kevin Collier


Published Feb 11, 2015   Updated May 29, 2021, 1:46 pm CDT

Americans, millennials, the civic-minded with a sense of humor, and everyone in between are all rightfully wringing their hands at the news that beloved Daily Show host Jon Stewart will retire later this year.

All but the stodgiest viewers have long accepted that just because Stewart has joke writers and a live, laughing audience, that doesn’t mean his content is any less serious than the network newscasts. Now that he is heading for the door, it’s worth remembering that he has put tough questions to some of the most important American political figures during his 16 years as Daily Show host.

Many of these interviews are split into multiple segments. We encourage you to click through to see the full conversations.

1) Donald Rumsfeld, 2011

2) Barack Obama, 2005

3) Chris Christie, 2012

4) John McCain, 2002

5) Nancy Pelosi, 2011

6) Barack Obama, 2012

7) Marco Rubio, 2012

8) Wendy Davis, 2014

9) Hillary Clinton, 2003

10) Hillary Clinton, 2014

11) Bill Clinton, 2007:

This video isn’t embeddable, but you can watch it here.

12) Rand Paul, 2011

13) Bernie Sanders, 2011

This video isn’t embeddable, but you can watch it here.

14) Colin Powell, 2005

15) John McCain, 2006

16) Henry Kissinger, 2003

17) Dennis Kucinich, 2003

18) Arlen Specter, 2000

19) Joe Lieberman, 2001

20) Bill Clinton, 2014

21) Jimmy Carter, 2015

Images via The Daily Show | Illustration by Max Fleishman

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*First Published: Feb 11, 2015, 3:34 pm CST