How Jon Stewart (and Obama) changed comedy

Obama to Jon Stewart: You're leaving before me?
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Story highlights

  • Dean Obeidallah: "Daily Show" interview highlights how Barack Obama and Jon Stewart both have changed their jobs
  • Obeidallah: Obama has brought deft comic touch to selling policy, skewering opponents
  • Stewart brought serious discussion of public policy into late-night comedy realm, he says

Dean Obeidallah, a former attorney, is the host of SiriusXM's weekly program "The Dean Obeidallah Show." He is a columnist for The Daily Beast and editor of the politics blog The Dean's Report. He's also the co-director of the documentary "The Muslims Are Coming!" Follow him on Twitter: @TheDeansreport. The opinions expressed in this commentary are solely those of the author.

(CNN)Social media lit up with clips of President Barack Obama's seventh and final appearance Tuesday on "The Daily Show." There's a reason for this.

Watching the President's valedictory interview with Jon Stewart, it was hard not to be struck by how much the two have in common. Neither has shown any fear in challenging people's views on hot-button issues, from racism to gun violence to the Middle East. Both have utterly redefined their respective jobs when it comes to comedy. Both, of course, have pissed off many, many people on the right.
Dean Obeidallah
And both are short-timers at their jobs -- relatively so, in Obama's case: He turns over his presidency on January 20, 2017, and Stewart ends his Comedy Central stint on August 6.
    How did these two redefine their positions from a comedic point of view? Well in Stewart's case, he has so eclipsed his predecessor, Craig Kilborn, that many don't realize that anyone else hosted "The Daily Show" before him. Kilborn, once described as having "frat-boy good looks and self-parodying smirk," did not exactly have public policy chops.
    But when Stewart took the reins in 1999, he not only transformed "The Daily Show," he redefined late-night TV comedy as a stage for political commentary. Before him, late-night monologue jokes featured mainly toothless, often unoriginal swipes at politicians. (I'm especially looking at you Jay Leno: "Yesterday President Bush was at Mount Rushmore. Don't confuse this with former President Clinton who was just in a rush to mount more.")
    Obama's last 'Daily Show'
    Obama's last 'Daily Show'

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    Obama's last 'Daily Show' 00:42
    And while Stewart doesn't shy away from bawdy jokes, he also routinely pauses -- often at length -- on complex issues from super PACs to the Palestinian-Israeli conflict to aid for first responders. Viewers often learned more about these issues from him -- while laughing -- than from traditional news outlets.
    In Obama's case, he followed George W. Bush, a guy who, like Kilborn, had a bit of a "frat boy" rap, a famous smirk and also was no heavyweight when it came to policy. Obama, as I have noted before, not only far eclipsed Bush in his use of comedy and his comic timing, he has likely forever changed the way presidents will use comedy going forward.
    First, the President has used comedy to reach out to Americans in nontraditional ways, such as when he showed his straight-faced comic timing in an appearance on Funny or Die's "Between Two Ferns" to sell Obamacare to younger people.
    But even more impressively, he has used comedy as a weapon. In the past, our presidents would generally use comedy in a self-deprecating manner. For example, Ronald Reagan joked about his advanced age, commenting, for example, that for his staff "preparing me for a press conference was like reinventing the wheel. Not true. I was around when the wheel was invented, and it was easier."
    Obama, on the other hand, has used comedy, like Stewart, to filet politicians with whom he has disagreed. We have seen Obama comically mock political adversaries such as House Speaker John Boehner, or Senate Majority Leader Mitch McConnell: "Some folks still don't think I spend enough time with Congress. 'Why don't you get a drink with Mitch McConnell?' they ask. Really? Why don't you get a drink with Mitch McConnell?"
    And he took a shot at super PAC funder Sheldon Adelson, "Did you know that Sheldon Adelson spent $100 million of his own money last year on negative ads? You've got to really dislike me to spend that kind of money. ... Sheldon would have been better off offering me $100 million to drop out of the race."
    Obama even gave "The Donald" the comedy equivalent of a body slam in 2011, the last time Trump was eyeing the presidency.
    Jon Stewart rips into Donald Trump
    Jon Stewart rips into Donald Trump

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    Jon Stewart rips into Donald Trump 01:29
    At that year's White House Correspondents' Association dinner, Obama gave us not one, but three jokes at Trump's expense, including this one that still resonates today: "We all know about your credentials and breadth of experience. ... In an episode of 'Celebrity Apprentice,' ... you, Mr. Trump, recognized that the real problem was a lack of leadership. And so ultimately, you didn't blame Lil Jon or Meatloaf. You fired Gary Busey." Obama, going in for the comedic kill, then added, "And these are the kind of decisions that would keep me up at night."
    And on Tuesday's "Daily Show," Obama and Stewart teamed up for a one-two punch mocking Trump. Stewart asked Obama if he had any advice '"to bequeath to future President Trump." Obama jokingly responded, "I'm sure the Republicans are enjoying Mr. Trump's current dominance," to which Stewart quipped, "Anything that makes them look less crazy."
    For me, and for many others, these two will be sorely missed. True, maybe their successors, Trevor Noah and Hillary Clinton ... or maybe Donald Trump or Carly Fiorina, will be just as good. But it will be awhile before someone will make us forget Obama and Stewart, who even as their respective tenures come to a close, are going out swinging.