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Bill O’Reilly is still picking fights with rappers, but it feels like his heart’s not in it. Ad Policy

On Monday night, O’Reilly hosted Lupe Fiasco, a 29-year old rapper and singer who recently dubbed President Obama a terrorist. The remark created an opening for O’Reilly to attack hip hop while getting Obama’s back. That’s a twist for Fox News, which usually attacks rappers by lumping them with Democrats, or rehashes the conservative complaints about “gangsta rap.” But the new angle couldn’t really save the segment.

O’Reilly dutifully presented his soundbites (“Obama is not a terrorist”), then turned to condescension, lecturing “Mr. Fiasco” that the word fallacious means wrong, and observing that few rap fans have political science Ph.Ds. Mr. Fiasco countered that his beef is not just with Obama, but with militaristic foreign policy, the root causes of terrorism and all American presidents. There was no fire, and very little substance, in the 5-minute exchange. (It’s a long ways from O’Reilly’s classic rap battles —like the spirited, lengthy 2003 debate he hosted between Damon Dash, Cam’ron and Salome Thomas-El, a black elementary school principal who felt that rap promoted obsccenity and negativity. )

O’Reilly has been obsessed with rappers as social and political leaders for over a decade, but the mainlining of hip hop in American culture has rendered his outrage rather quaint.

“The conventional wisdom is that attacking a rapper is good for high drama,” says Jay Smooth, a hip hop radio host who also does political commentary on the video blog illdoctrine.com. He argues that nowadays, however, rap has become “a bland middle American product like any other,” pointing to this year’s Superbowl, which included three different luxury car ads by rappers (Eminem, Jay-Z and Diddy). “That was a big landmark to me of how far hip hop has come into the safe mainstream,” Smooth told The Nation. Meanwhile, the conservative critique still assumes people think rapper is a dirty word.

As for O’Reilly’s enduring fascination with his hip hop adversaries, real and imagined, Smooth has that figured out, too:

"I’ve always had a theory that O’Reilly sees rappers as kindred spirits —sees a lot of himself in their bravado. He’s always had this mix of declaring himself the master of ‘the no spin zone,’ and ‘keeping it real’ the whole time, but he’s doing a contrived persona that is calculated to keep people watching, which is similar to commercial rappers."

Smooth first spotted this connection in 2007, in an irreverent music video taking O’Reilly’s MC fetish to the next level. (Hint: it rhymes. Video below.)

And back to Monday’s interview, it would not be complete without some post-show sparring. Later in the evening, Lupe Fiasco went online to complain that some of his sharpest arguments were edited out of the segment. He had charged, for example, that U.S. military manuals “teach you how to be a terrorist.” He tweeted the claim to his 670,000 followers, hastening to add that his father was a Green Beret and he’s “not against the military.”

Well alright. Branding opponents terrorists is a destructive tack, obviously, from any corner of the spectrum. Still, Lupe’s lyrics are more compelling than his punditry. Take “Words I Never Said," the new song that started this controversy, where he raps about the War on Terror and the sensationalism of the news media:

I really think the war on terror is a bunch of bullsh**/

Just a poor excuse for you to use up all your bullets…

Your childs future was the first to go with budget cuts/

If you think that hurts then, wait here comes the uppercut

The school was garbage in the first place, that’s on the up and up/

Keep you at the bottom but tease you with the uppercrust If you turn on TV all you see’s a bunch of “what the f*cks

‘Dude is dating so-and-so, blabbering ‘bout such and such/

And that aint Jersey Shore, homie —that’s the news!

And these the same people that supposed to be telling us the truth

Limbaugh is a racist, Glenn Beck is a racist

Gaza strip was getting bombed, Obama didn’t say sh*t

Thats why I aint vote for him —next one either/

I’m a part of the problem, my problem is I’m peaceful

And I believe in the people.

So Lupe on politics is more interesting than Lupe on Lupe — and definitely more worthwhile than Lupe on O’Reilly.

Videos below:

Jay Smooth’s O’Reilly video:

Lupe Fiasco’s music video:

The Fiasco-O’Reilly debate: