In 1968, Harry Bellafonte, an African-American singer best known for his single “The Banana Boat Song (Day-O),” appeared on television to perform a televised anti-war duet with caucasian singer Petula Clark. Near the end of the song, Clark touched Belafonte, grabbing hold of its bicep. It shouldn’t have been a big deal, but it was. The program’s sponsor Chrysler tried to have the take removed from the special, believing a white woman touching a black man on television would offend Americans.

In many ways, it’s an incident that typifies the troubled racial history of the American music industry. Though protest songs have been at the forefront of many progressive movements, most notably the ‘60s Civil Rights movement, the record labels and sponsors often resisted racial progress in their own industry.

These five artists are among the many who actively fought to break down the barriers to black musicians despite all the resistance, transforming the racial and musical landscape of America along the way.

Sly and the Family Stone

Sly Stone worked in favor of musical integration long before he was famous, starting by playing songs by white artists while he was a DJ at the San Francisco-based black-oriented station KSOL.

Sly and his band the Family Stone emerged as the first racially integrated, multi-gendered rock band in 1967, attracting black listeners for their gospel-tinged soul vocals and whites for their outrageous costuming and psych-rock influences.

Sly ignored calls from Black Panther activists to replace the band’s two white musicians, Gregg Errico and Jerry Martini. Not only did Sly and the Family Stone represent peaceful integration at a time when the entire nation was transitioning away from “separate but equal” facilities, they also invented a musical style that reflected the diversity of their lineup, incorporating elements of rock, soul, Motown, gospel and psychedelia into their sound and singing lyrics that pleaded for peace and love over prejudice on protest anthems like “Everyday People” and “Stand!”

Ray Charles

Ray Charles found crossover success in the late ‘50s with hits like “What’d I Say,” earning him enough clout to sign a deal with ABC that granted him an unprecedented degree of creative control over his output — at a time when most successful black artists were completely controlled by their labels.

With fans on both sides of the racial divide, Charles famously refused to play a segregated show at the Bell Auditorium in his hometown of Augusta, GA. He was fined for breach of contract and didn’t play in his hometown until it was desegregated.

His eclectic musical tastes led him to record Modern Sounds in Country Western Music and its sequel, Vol. 2 — two wildly successful albums featuring covers of country standards. Charles enjoyed a sudden influx of white fans, and the album immediately brought country music closer to the mainstream of pop music, firmly demonstrating, just as he did with soul music, that the genre shouldn’t be limited to one race. The first album alone spawned four charting singles that became staples for soul and country stations alike, and Willie Nelson said it “did more for country music than any one artists has ever done.”

Marvin Gaye

Soul music pioneer Marvin Gaye enjoyed enormous success in the ‘60s Motown scene, first as a session player and then as a solo artist, but unlike Charles, he was forced to work under the thumb of a controlling record label and a label head, Berry Gordy, who made him feel like nothing more than a “puppet.”

Gaye became one of the first Motown artists to wrestle creative control away from the label with his 1971 album What’s Going On, a landmark in socially-conscious music that precipitated a wave of politically-charged soul music. Gordy refused to release the album’s title track, a pained response to an act of police brutality at a Berkeley anti-war rally, saying he felt it was “too political.” Gaye responded by going on strike until the label agreed to release the song. It reached No. 1 on the R&B charts within a month of release, and the album became Gaye’s first to sell one million copies and spawned two more Top 10 singles.

His bold act of defiance paid off big, and the same year Gaye re-signed with the Motown label for a $1 million contract, then the most lucrative deal ever offered to a black recording artist.

Michael Jackson

In its early days, MTV heavily favored rock music and white artists. Then, in 1983, Michael Jackson released his album Thriller, along with videos for two lead singles, “Billie Jean” and the album’s title trck. Both iconic videos enjoyed heavy rotation on the channel — allegedly only after Michael’s label CBS threatened to pull their other artists and programming from the network — cementing Jackson’s reputation as the King of Pop and all but inventing modern music videos.

White-oriented radio stations that played Jackson’s songs like New York’s WPLJ endured protests from enraged listeners, but that couldn’t stop his runaway success. Before long, Jackson was partnering with Pepsi for an enormous promotional deal and MTV regularly featured other black artists on programs like Yo! MTV Raps.

Public Enemy

Public Enemy was among the first acts to bring hip-hop music to broader attention, and they managed it without ever compromising an ounce of their incendiary political messaging.

Politically motivated hip-hop was a rarity before the release of Public Enemy’s first album, 1987’s Yo! Bum Rush the Show, which earned critical acclaim and established the band’s strongly pro-black political stance.

Their first four albums have been called “the most acclaimed body of work ever by a hip hop act.” Their most powerful statement came with their 1989 track “Fight the Power” and its accompanying Spike Lee-directed music video. The video begins with band member Chuck D denouncing the optimistic speeches of the ‘60s Civil Rights movement, saying that “young black America… ain’t goin’ out like that ’63 nonsense,” and then shows a black power protest against racially-motivated violence in Brooklyn’s Bed-Stuy neighborhood. The song aimed to give young black Americans in the turbulent, politically conservative ‘80s a civil rights movement of their own, and it’s still regarded as one of hip-hop’s greatest tracks.