Malcolm X and rap music have always fit together like a needle in the groove, connected by struggle, strength and defiance. But three recent episodes involving the use or misuse of Malcolm and other black icons have raised the question: Has rap lost touch with black history?

Chart-topping rapstress Nicki Minaj provoked widespread outrage with an Instagram post featuring one of black history’s most poignant images: Malcolm X peering out the window of his home, rifle in hand, trying to defend his wife and children from firebombs while under surveillance by federal agents. Superimposed on the photo: the title of Minaj’s new song, which denigrates certain black men and repeats the N-word 42 times.

That came after Minaj’s mentor Lil Wayne recorded a verse last year using the civil rights martyr Emmett Till in a sexual metaphor, and the hip-hop mogul Russell Simmons posted a Harriet Tubman “sex tape” video on his comedy channel.

What is happening to mainstream rap music, which was launched by Simmons and is now ruled by the likes of Minaj and Wayne?

“I don’t want to say today’s rappers are not educated about black history but they don’t seem as aware as rap generations before them,” said Jermaine Hall, editor-in-chief of Vibe, the hip-hop magazine and website.

While previous generations had to struggle with the racism and neglect of the 1970s or the crack epidemic of the 1980s, Hall said, today’s young people have not faced the same type of racial struggle: “They’re sort of getting further and further away from the civil rights movement.”

“In the ‘80s, whether it was KRS-One, Public Enemy or the Native Tongues, that entire movement, it was very in tune with black history,” Hall said. “They knew everything about Malcolm, about Martin, about Rosa Parks. Now, the new rappers just aren’t as in tune.”

Indeed, Minaj issued a statement expressing disbelief at the uproar and apologizing to Malcolm’s family “if the meaning of the photo was misconstrued.” Wayne wrote to the Till family to “acknowledge your hurt, as well as the letter you sent to me via your attorneys.” Simmons was the only one to say, “I am sincerely sorry.”

The apologies did not change much for Pierre Bennu, a filmmaker and artist who said Malcolm X’s life was dedicated to advocating for the humanity of black people, while Minaj’s song was simply dehumanizing. When he saw Minaj’s manipulation, Bennu said, “I felt punched in the gut.” The episode inspired him to post a mash-up video (http://bit.ly/1fpoFYB) laying Minaj’s song over the infamous 1941 Walter Lantz cartoon Scrub Me Mama With A Boogie Beat, which depicts a town of lazy black people hypnotized by a seductive washerwoman.

Various mainstream rap artists seem reluctant to defend Minaj and Wayne; The Associated Press sought out five but none returned calls for comment. Jasiri X, a rapper whose music focuses on black empowerment and current events, said many of today’s mainstream rappers use images of revolutionary black icons to promote an anti-establishment image.

“All the while, they’re being funded and pushed by major corporations,” he said. “I see Nicki and other artists, whether Kanye or Jay Z, adopting these revolutionary images or using a clip or saying their name but never practice the principles which these revolutionaries gave their lives for,” Jasiri said.

It wasn’t always so. Hip-hop began in the early 1970s as an alternative to gang activity. Before the music was recorded, founding fathers like DJ Afrika Bambaataa – whose slogan was “peace, love, unity and having fun” –  would play Malcolm X’s voice over instrumental break beats.

“Not only did it sound funky but it helped raise our consciousness,” hip-hop historian Davey D wrote on his website. Davey attended many early rap concerts at Harlem’s Audubon Ballroom, where Malcolm was assassinated. As the music gained steam, X was constantly honored on wax. KRS-One duplicated Malcolm’s gun-in-the-window pose on the cover of his 1988 classic album, By Any Means Necessary. In 1991, Tupac rhymed on Words of Wisdom: “No Malcolm X in my history text, why is that?/Cause he tried to educate and liberate all blacks.”

Malcolm’s voice and image appeared on so many records and videos, “many would remark that he was an emcee,” Davey wrote. Tubman also is a longtime rap staple, mentioned by everyone from Ice Cube (“She helped me run like Harriet Tubman”) to Pharoahe Monch (“A railroad to underground like Harriet Tubman”). Till, too, has been mentioned in songs such as Kanye’s breakthrough 2003 single Through The Wire.

But today’s rappers reflect our money-obsessed society, said Bakari Kitwana, whose Rap Sessions organization just moderated a series of community dialogues between the civil rights and hip-hop generations.

“We see a lot of things going on with our young people and we don’t feel like we are teaching them values that can compete with the way the value of money is ingrained in our culture,” Kitwana said. “Everything is just focused on money. If you can get money, whatever else you’re doing doesn’t matter.”

“It’s reached a crisis point,” he said. “I came up in the ’70s and ’80s and greed has always been present but I don’t think I’ve ever seen it like it is now.” He was echoed by Paradise Gray, who performed in the 1980s with the Afrocentric rap group X Clan.

“Mainstream rap music has lost its reverence for anything besides money,” Gray said.

Today’s rappers threaten to kill people who disrespect them “but they sit back and let you disrespect our legacy, our culture, our history,” he said. “What,” Gray asked, “will the disrespect of your humanity and your blackness cost you?”

Jesse Washington covers race and ethnicity for The Associated Press. He may be reached at www.twitter.com/jessewashington or jwashington@ap.org