Founder of the political Hip-Hop group The Coup, Boots Riley is a musician, rapper, writer, and activist. One of the leading artists of our time. His “Sorry to Bother You” feature film which he wrote and directed, received the award for Best First Feature at the 2019 Independent Spirit Awards (amongst several other accolades and recognitions).  Riley himself was nominated this year by the Director’s Guild of America for Outstanding Directorial Achievement (First-Time Feature Film), while “Sorry to Bother You” received two 2019 Critics Choice Award nominations for Best Actor (Comedy) and Best Film (Comedy). 

On Saturday May 11th 2019 at Knox United Church in Winnipeg, I was fortunate enough to hear Boots Riley speak. The hall was filled to capacity with over 1,200 people, all glued to their seats and listening intently to a man of small stature. A man who had monuments to say. I had no idea on that evening then that I would attempt to write about Boots Riley a year later. If I had known, I most certainly would have taken notes. 

Boots was invited to speak at the church by the Canadian Centre for Alternative Policies to celebrate the anniversary of the 1919 General Strike. Riley’s work and activism meaningfully reflects everyday life and people. Whose main mission in life is to use music, words, film to evoke change and instil justice and equality. 

He started the evening on May 11, with his rap song called “ Underdogs” The underlying meaning behind the song is that making a change to the system is part of loving yourself. Boots never really ended the evening, and it was clear that the engaged audience did not want this night to end. The question and answer session proved this. It seemed to last forever, especially once the topic of Venezuela got started. This clearly was a man whose politics and art were one. 

During the after party Boots was trapped by so many people who wanted to engage him with their accolades. The unassuming Boots, patiently answered everyone’s questions and listened intently. This was a man who cared. 

That night, I became the proud fan, who now possessed his book, titled Boots Riley Tell Homeland Security- We are the Bomb. Complete with autograph. But I did not want to take up too much of his time, as I could clearly see he was swarmed by fans. 

Boots film “Sorry To Bother You” had just been released across North America.  The shows sold out in advance at Winnipeg’s Cinematique. (yes, it is a small theatre) I was lucky enough to get a ticket, arrived early for a good seat, and sat with anticipation in the theatre. 

“Sorry To Bother You” was mesmerizing to say the least. The political puns, the visual humour, ingeniously conceived stunts all added up to a vision of revolution in this thought provoking social satire. With mega stars like Lakeith Stanfield who plays a struggling telemarketer named Cassius Green. Cassius discovers a magical key to professional success which propels him into a macabre universe. The stellar cast also includes Tessa Thompson, alongside Armie Hammer, Steven Yeun, Danny Glover, Jermaine Fowler, Terry Crews, and Omari Hardwick. Indeed Boots takes aim at corporate greed, racism, class and struggle, art and technology, and the prison industrial complex. Boots’ aim is spot on. 

This is the  kind of film you have to see more than once to soak it all in. There is one scene in the film, where Cassius Green is asked by the white rich folk to spontaneously break into a rap. This particularly poignant scene speaks to the heart of the film. The white rich folk want Cassius to represent “dangerous, cool, and sexy,” which is the rebelliousness minus the rebellion. It reeked of a deep repugnancy towards ignorance with an accurate amount of disgust.

I must confess that because I had worked in Oakland, where the film was made, I was also particularly interested to see scenes from the streets of Oakland. But that is not why the film was made. Not to show off the neighbourhood. It is because Boots would have had a genuine interest in employing and working with his fellow comrades. Boots grew up in Oakland and has an extensive history of fighting for social justice. His father was the civil rights lawyer and organizer Walter Riley. 

You know when you get a taste of Boots music or lyrics, that he is never going to back down, yet he infuses humor in all his work. His group, The Coup, of which Boots is founding member, is one of Hiphop’s most fiercely loved, provocative, subversive, and humorous groups. 

Boots himself says he believes people respond to humour, and he is very optimistic about peoples’ ability to change the world. 

According to Boots from his book, Boots Riley Tell Homeland Security- We are the Bomb. “The things that I think motivate people into auctioneer not doom and gloom, and not anger and rage, the things that I think actually motivate people into action are optimism and hope.” 

Is there is an appetite across the United States for drastic change? It is an obvious yes. All we have to do is look at who is occupying the white house currently and pay attention to the surge of activist movements such as Occupy Wall Street and Black Lives Matter, as well as strikes around the United States.  

It was shortly after Occupy Oakland that Boots wrote “The Guillotine” which is about the power the working class has to change the system and get rid of the ruling class. “To me, the Occupy movement is a simple acknowledgement of a class war that was declared against the “99%,” a war that has resulted in the dismantling of the labor movement, an escalation of the war on drugs, the growth of the prison- industrial complex, cuts in school and domestic programs, and a consolidation of wealth and power by corporations that has put them beyond the reach of any governmental body. The rich have gotten richer, the poor have gotten poorer, and ignoring it ain’t working.” 

Captain Sterlings Little Problem 

Honestly, my all time favourite poem written by Boots Riley is Captain Sterlings’ Little Problem. It is a slap in your face, or maybe I should say Captain Sterlings’ face, and everything he symbolizes. It speaks to several generations. Timeless and pertinent in every direction you decide to take it. It makes such a profound statement and yet it also makes the reader laugh (at Captain Sterling’s expense of course). It also reminded me of the recruiters who frequently visit schools to find young people to get them to join the army with a pack of glamourized false promises. This is allowed because the No Child Left Behind Act, signed by President George W. Bush in 2002, requires military recruiters be granted the same access in schools as college recruiters. Another favourite is Five Million Ways To Kill A CEO and it is basically about CEO’s killing themselves with their own greed. The music and poetry of Boots Riley is far reaching. He does not preach, he just pretty much says it like it is. And with humour. Music for a revolution. 

Boots is currently working on a second film about a twelve foot black man who lives in Oakland. I will be one of the first in line to get my ticket when it is released. And by the way, thanks for the autograph Boots.

Warning: the film “Sorry to Bother You” has content (drugs, sex, violence, horror) that could potentially scare children or teens. This is an adult film. 

You can purchase Boots Rileys book Boots Riley Tell Homeland Security- We are the Bomb on Amazon

And his film Sorry to Bother You on Amazon