How Rappers Like Boots Riley Are Opening The Door For Directing As A New Hustle

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For the longest time, the path from hip-hop stardom to Hollywood seemed set. The blueprint offered by trailblazers like Ice Cube, Will Smith, Queen Latifah, and LL Cool J became the most reliable post-rap retirement plan around.

Once a rapper had reached a certain level of musical achievement, their audience of fans could be flipped for roles in action blockbusters or family comedies, resulting in a comfortable second act as a movie and television star. However, in recent years, with the success of freestylers-turned-film-directors like Ava DuVernay and Boots Riley, it appears that a new path has emerged, one that hadn’t been as evident, but is no less fulfilling creatively. Whereas before, rappers major route to post hip-hop success was as a box-office draw, now there is another road to Hollywood’s heralded halls: Direction.

This past week, Bay Area rapper and activist Boots Riley released his directorial debut, Sorry To Bother You to rave reviews from both critics and general audiences after a near 30-year career as frontman of political hip-hop band The Coup. The group has released six albums and two EPs, as well as countless music videos, yet Boots is currently experiencing the heights of mainstream success as he promotes the film, which tackles much of the same subject matter as his socially conscious music. The Coup often critiqued capitalism, police brutality, and American politics, Sorry To Bother You does the same, just in a different medium, one with an arguably much greater reach.

Meanwhile, Ava DuVernay has become the toast of the town as a director of the multicultural, big-budget adaptation of popular children’s novel A Wrinkle In Time starring Oprah Winfrey, Mindy Kaling, and Gugu Mbatha-Raw. Its global box office take of $132.7 million makes DuVernay the first Black woman to direct a film that earned at least $100 million at the box office. She was also the first Black female director to be nominated for both a Golden Globe and an Academy Award for Best Picture for her Martin Luther King Jr. biopic, Selma.

Yet, a somewhat overlooked part of her narrative is one of the most intriguing. Before any of her successes as a director, she was a member of jazz-rap duo Figures Of Speech as MC Eve, performing at open mics at the legendary Good Life Cafe in Los Angeles alongside underground rap luminaries like Jurassic 5 and Freestyle Fellowship. In fact, her very first film as a director was a documentary about the open mic sessions there titled This Is The Life, released ten years almost to the day before A Wrinkle In Time. Her next big project? Helming another adaptation, this time of DC Comics’ The New Gods.

Ava and Boots’ recent successes are a testament to the new pathways opening up for rappers seeking new creative outlets or jobs in entertainment. It’s no longer necessary to step in front of the camera; there are expanding opportunities for aspiring hip-hop entertainers to tell their stories behind the camera as well. It wasn’t always like this, but as hip-hop has increasingly become the language and the look of modern pop culture, it’s less and less strange to see former rappers branching out into an expanded pool of possibilities for life after rap.