Great Moments in Late Night Politics

By PopEater Staff Posted Sep 21st 2009 04:00PM

Like him or not, it's no secret that Barack Obama is one telegenic cat. Given the amount of political soap to sell and the politicians who need to sell it, it shouldn't be a surprise that Obama has been on 'The Late Show with David Letterman' five times. But Monday night's episode is a big deal because it is the first time in 'Late Show' history that a sitting president will be a guest. Yep, President Obama will visit Dave for an hour and yuk it up about health care. Here's hoping we won't need an aspirin afterwards ...

To mark the occasion, here's a list of stand-out Political Moments in Late Night.

McFeud

David Letterman can be a prickly pear sometimes. Make that most of the time. And what pisses Dave off is when a guest for his TV show doesn't show up. But what makes him even more ornery is when the guest scheduled for his show winds up being interviewed somewhere else. Ladies and gentlemen, the runner up for POTUS (President of the United States) ... John McCain, a.k.a. The Man Who Wasn't There.

Dole Pops Up

Viagra causes baldness? Or was that blindness? During Jay Leno's 'Tonight Show' monologue, a special visitor from Kansas pops up. Har. Hardy har har. For those keeping score, that joke officially landed below the belt. Or was it "beltway"?

Sax Man

Then-Governor Bill Clinton was trying to reach a younger audience when in 1992 he brought his saxophone skills to Arsenio Hall's now-defunct show.

A Bad Joke Reverberates

A joke is a joke is a joke. Unless it's about Willow Palin, the 14-year-old daughter of former Republican Vice Presidential nominee Sarah Palin. After being informed that one of Dave's jokes about Willow was tasteless, Dave humbly apologizes. Well, kind of.

One Tough Cheney

Jon Stewart usually spends the second half of 'The Daily Show' talking to political guests. But when his preferred guest has been secreted away in a bunker for most of the Bush administration, Stewart turns to the next best option. His wife. Jon Stewart can be pretty intimidating. And so can Dick Cheney. But you haven't seen intimidating until you've seen the wife of the former Vice President, Lynn Cheney.

Who Booked This Guy?

Sometimes it takes some time for the storm to gather speed. In this clip, Stephen Colbert skewers the Bush White House during the 2006 White House Correspondents' Association Dinner, invoking shivers of silence in the room. Although it received little attention early on, James Poniewozik of Time magazine called the speech "the political-cultural touchstone issue of 2006."

Who Created Huckabee?

Former Arkansas Governor Mike Huckabee took the Republican party by storm, finishing second in the 2008 Presidential primaries. But what was his secret? Was it his Conservative background? His "aw shucks" demeanor? Or how about his ad featuring Chuck Norris? (Seriously there was such an ad.) But maybe, just maybe, it was the work of Conan O'Brien, Stephen Colbert and Jon Stewart. Here the boys fight it out for bragging rights for the political juggernaut known as Mike Huckabee.

Reverence

And finally, it just wouldn't be right unless we ended where we started. With Dave. Here's David Letterman during his first broadcast after the 9/11 attacks. Could a funny man be so serious? Touching? And eloquent?