When Jay-Z and Kanye West perform in Washington tonight, it will be an interesting collaboration not just musically, but also politically.

The two hip-hop superstars have very different reputations in D.C.

Jay-Z is a longtime supporter of President Barack Obama who got prime seats at the 2009 inauguration and was once photographed in the Situation Room of the White House with his wife, Beyoncé Knowles.

West is famous for arguing during a TV telethon after Hurricane Katrina hit New Orleans that President George W. Bush didn’t care about black people — a moment the president later called a low point in his administration — and was offhandedly derided by Obama as a “jackass” for interrupting fellow musician Taylor Swift at an awards show.

Touring in support of their chart-topping collaborative album “Watch the Throne,” the pair is actually quite representative of the relationship that hip-hop has shared with official Washington over the years. 

It’s a history marred by misunderstandings, aggressive criticism from both sides and the occasional bizarre interlude, such as a gangsta rapper hanging out with a GOP president. 

More than any other genre of music, hip-hop has struggled to find solid footing in the political world.

“Even though hip-hop is a part of Americana right now, it’s tenuous when it comes to people trying to place it in the mainstream, especially in politics,” said Marcus Reeves, author of “Somebody Scream: Rap Music’s Rise to Prominence in the Aftershock of Black Power.” “Hip-hop is not as outspoken as it once was, but it’s still affiliated with a part of society that is something you might want to shun.”

Recent events show the awkwardness has continued. 

Earlier this year, criticism flared from conservative pundits and New Jersey state troopers after rapper Common was invited to appear at a White House poetry event. 

Common — a socially conscious Chicago rapper who has appeared in Gap commercials — was protested for a track empathizing with a Black Panther convicted of murdering a New Jersey police officer.  

Compare that to a 1991 White House visit made by now-deceased Eazy-E, a former member of N.W.A. — known to many for their song “F— tha Police” — at the behest of the National Republican Senatorial Committee, an event that drew little public criticism.

Vance Levy, a native D.C. rapper who performs as Head-Roc, said partisan and racial politics explain the difference between the receptions given to Eazy-E and Common.

“I think that was a reaction to the country’s first black president,” he said. “It’s [also] a clear indicator of the mindset of the two-party system.”

Chris Richards, the Washington Post’s pop music critic, saw the incident as indicative of a larger conundrum for Obama. 

“It seems like [the White House] is in a difficult position, because the hip-hop community has supported the president, but when he shows support back, it opens him up to criticism,” he said. “It’s a tightrope act, and they’re still figuring that one out.”

The Obama administration is not the first to have a tenuous relationship with hip-hop. In 1992, then-candidate Bill Clinton responded to racially controversial comments by the female rapper Sister Souljah by implying that the musician’s views were comparable to those of white supremacist David Duke.

While some in the hip-hop community were disappointed at Clinton’s reaction, the “Sister Souljah moment” was also seen as a way for Clinton to curry favor with white voters uncomfortable with liberal elements of the Democratic base.

That same year, Ice T’s band Body Count released its self-titled album with the single “Cop Killer,” drawing the ire of Vice President Dan Quayle and Tipper Gore and helping to usher in the creation of the “Parental Advisory” labels that still adorn albums covers.  

And West was certainly not the only rapper to take shots at Bush for his handling of Hurricane Katrina — New Orleans rapper Lil Wayne closed his massively popular 2006 “Dedication 2” mixtape with “Georgia … Bush,” a song which not-so-subtly suggests the government may have been behind the damage to the city. 

Despite these flare-ups, Jay-Z may be at the helm of a new era in relations between hip-hop and Washington. Richards and Reeves both pointed to the role of the hip-hop community in the 2008 election.

Obama’s body man, Reggie Love, reportedly added some hip-hop tracks to the candidate’s iPod. During an event in North Carolina, Obama even seemed to some to reference the Jay-Z song “Dirt Off Your Shoulder” in response to criticism from primary rival Hillary Clinton. 

“What helped solidify Obama with the next generation was his popularity with hip-hop,” Reeves said. “It showed that the generation that helped get him elected thought about race and power differently than their parents.”

But it is that move toward mainstream influence that remains the major difference between the two poles occupied by Jay-Z and West.  

On the one hand, there’s Jay-Z, the reformed street hustler turned business deal-maker who now moves with the biggest power broker in all the land. “Jay-Z’s no longer a gangsta rapper, he’s a corporate figure who raps,” Reeves said. “Everyone loves the underdog who overcomes, and Jay-Z represents that. But he’s now about as cuddly as anything in pop culture.”

And on the other hand there’s West, the iconoclastic loudmouth, eager to break into the corridors of power but appearing to lack the impulse control necessary to achieve his ambitions.

“Washington is a place where cooperation helps you succeed in a lot of ways, and Kanye doesn’t seem to care about anything but his art and what he wants to say,” Richards said. “There are no Kanye Wests in Washington. That kind of character doesn’t really exist here.”