As Jon Stewart heads into the final stretch of hosting “The Daily Show,” Truthdig has chosen some of our favorite segments from both his popular Comedy Central news satire and other news shows on which he appeared—usually to the chagrin of those shows.

These clips are meant to celebrate his best moments: Whether he was exposing political dysfunction, excoriating corporate media or showing the folly and corruption of the powerful, Stewart made palpable the wrongdoing within the corporate system.

The segments below contain interviews in which Stewart either took on or poked fun at his guests in a manner that exposed not only major flaws in their public persona, but the hypocrisy of the image they were trying to project to the public.

The first segment shows an infamous interview with “Mad Money” host Jim Cramer. “I understand you want to make finance entertaining, but it’s not a fucking game,” says Stewart, exposing Cramer’s callous intent in knowing the illegalities yet still exonerating Wall Street for its part in the 2008-09 financial meltdown while simultaneously blaming the middle class.

(The first clip, provided by “The Daily Show,” has audio that is not in full sync with the video.)

The following segment is with Bill O’Reilly, Fox News pundit. O’Reilly and Stewart have interviewed each other over the years and even took part in a fake debate in 2012. Stewart often held up O’Reilly as an example of the extreme political views Fox News espouses.

Our final segment is from an interview with former Vice President Al Gore, in which Stewart asks if “mogul” Gore can coexist with “activist” Gore. Stewart exposes the hypocrisy of allowing “fossil fuel money” to buy Gore’s news station, Current News, given his frequent criticism of the fossil fuel industry.

— Posted by Donald Kaufman.

Your support is crucial...

As we navigate an uncertain 2025, with a new administration questioning press freedoms, the risks are clear: our ability to report freely is under threat.

Your tax-deductible donation enables us to dig deeper, delivering fearless investigative reporting and analysis that exposes the reality beneath the headlines — without compromise.

Now is the time to take action. Stand with our courageous journalists. Donate today to protect a free press, uphold democracy and uncover the stories that need to be told.

SUPPORT TRUTHDIG