This article appeared in the September 19, 2025 edition of The Film Comment Letter, our free weekly newsletter featuring original film criticism and writing. Sign up for the Letter here.
Penitentiary (Jamaa Fanaka, 1979). Courtesy of Vinegar Syndrome.
When North Carolina’s Central Prison showed the buddy comedy Life (1999) to the incarcerated population in 2004, I couldn’t sit through more than 30 minutes. The film, starring Eddie Murphy and Martin Lawrence, follows a pair of bootleggers from New York who are wrongly convicted of murder and sent to prison for life in 1930s Mississippi. My friends laughed until they lost their breath. But at 25 years old, I had already served two years on a life-without-parole sentence for murder. Watching a multitude of caged Black men—like me—on screen didn’t seem entertaining, no matter how much I loved going to the movies.
Movie night on Fridays at Central Prison brought me as close to the free world as I could get. My friends and I brought chips, sodas, and pints of ice cream to the packed auditorium. For 120 minutes, I escaped prison to marvel at spies uncovering diabolical plots for world domination, underdogs overcoming humble origins to achieve great things, and visuals of exotic locales that I will never see in person while serving life.
But watching films about prison while incarcerated destroyed my idea of escapism. I didn’t like how these films relied on stereotypes about prisoners to carry a story. Often, they portray violence as the accepted consequence for men who express vulnerability instead of toughness. They reinforce society’s image of the common prisoner as a hypermasculine thug who could never rehabilitate. In these movies—like Gridiron Gang (2006), Undisputed (2002), and The Longest Yard (2005)—Black prisoners are no better than happy slaves in minstrel shows of yesteryear. The characters I saw didn’t depict my reality, so I shunned them.
Despite my concerns about prison movies, I understand the Hollywood motive. Portraying a convicted killer as a hero is challenging. A rusty shank will never gleam brighter than Excalibur. So heroes in prison films are usually innocent and relatable to a Caucasian audience, which is a far cry from who really fills American prisons.
I didn’t always dislike films about prison. Before my incarceration, I enjoyed quite a few. Bad Boys (1983) was the first prison film I remember liking as a teen. In it, 16-year-old Mick O’Brien (Sean Penn) is sent to a wild youth prison after he crashes a stolen car during a drug deal gone wrong, killing an 8-year-old boy. The boy’s older brother, Paco Moreno (Esai Morales), assaults Mick’s girlfriend in a bid to be sent to the same prison, so he can avenge his slain sibling. Mick, forced to fight for his life (wielding, in one scene, a pillowcase stuffed with unopened soda cans for self-defense), becomes a redeemable character. I appreciated Bad Boys because it depicted an underdog besting his enemies, but back then I didn’t pick up on the subtext: that a criminal can be a relatable, likable character only if he’s a rebellious white teen.
The 1970s Blaxploitation films like Penitentiary (1979), which I found in my father’s pirated VHS collection as a teenager, presented a different kind of criminal—and a different kind of relatability. The film’s hero, Too Sweet (Leon Isaac Kennedy), lands in prison unjustly, and as his first test, must fend off the notorious prison predator Half Dead (Badja Djola). I giggled when the Afroed soul brothers in the film schemed to hoodwink the racist white lieutenant, but I was too naïve, then, to understand the film’s true message.
Too Sweet represented the emerging “Black tough” of the 1960s and ’70s, when Black Americans were redefining their identity after the end of segregation. Back then, America weaponized incarceration to silence Black activists, like members of the Black Panther Party. In response, these activists instigated prison riots from Soledad in California to Attica in New York, and even Central Prison in North Carolina. Solidarity behind bars furthered the social revolution. Penitentiary embodied a newly discovered Black bravado, as did other countercultural Black films of that time, like Super Fly (1972) and The Mack (1973), in which even pimps could be protagonists as long as they were tough enough to trump the racist authorities. Those films paved the way for modern films like Hustle & Flow (2005), starring Terrence Howard.
Some movies incorporate prison as a rite of passage a hero must endure for personal growth. To conquer prison, the hero meets a wise mentor. In Malcolm X (1992), Malcolm Little (Denzel Washington) encounters incarcerated Muslims who help him kick dope and find his voice as a leader. In South Central (1992), Bobby Johnson (Glenn Plummer) meets a father figure who helps him earn parole so he can get out to raise his young son. Mentors in prison films guide broken souls from a path of self-destruction to one of righteousness, something I experienced in my own life. As a 24-year-old lifer, I met a man I’ll call Bobby Sinclair, a Black Army veteran who had been serving life for murder since 1977. He taught me kung fu in secret at Central Prison so that I wouldn’t join a gang. Along with showing me shadow kicks and battering-ram punches, Sinclair helped me navigate prison by teaching me the intricacies of dealing with other convicts. Without his mentorship, I probably would’ve joined a gang, making my life one of turmoil instead of accomplishment.
In Sing Sing (2023), Colman Domingo plays John “Divine G” Whitfield, an incarcerated playwright serving decades for a crime he didn’t commit. Divine G struggles with repeated denials of parole and the unexpected death of his friend Mike Mike (Sean San José), but somehow, he mentors and reshapes the life of a thug named Clarence “Divine Eye” Maclin (cast as a dramatized version of himself) through a program that enables incarcerated folks to put on plays in prison.
Unlike Divine G, I am not an innocent man, so I can’t identify with his struggle to clear his name. In 2002, a North Carolina jury convicted me of killing a man after trying to rob him during a drug deal. I needed cash because I had recently been released from a year in prison for petty crimes, and was then homeless. To thwart the robbery, he pulled out a black plastic pistol that I mistook as a deadly firearm. When I fired my gun, I thought I was protecting myself. The courts ruled differently. Since being incarcerated, I have published a plethora of writings, pursued higher education, and taught my peers in a writing workshop, but I remain in prison—after 23 years—with no hope for release. Worse, I live with the regret of having killed someone who couldn’t have hurt me.
My horrid character arc will never inspire a feature film. But Sing Sing reflects my grief, my temptation to give up hope, and my fear of dying in a cage. As a writer, I relate most to how Divine G leans on his art as a crutch. I couldn’t view him as a character in a film. Divine G represented every man I pulled time with. And when he was too strong to cry for himself in the film, I cried for him.
Sing Sing gave me the courage to finish watching Life when it aired on cable TV recently, more than 20 years after I walked out on it. This time, Bernie Mac made me laugh until my stomach hurt. Even though the film parodies the hardships of incarceration, I recognized an overarching theme of resilience. The main characters, Ray and Claude, never stop seeking freedom, even after a half century behind bars. They survive three acts of conflict by hoping when life seems hopeless. Ever since then, I’ve stopped viewing prison films as a source of entertainment, and now I embrace them as a wealth of inspiration.
Phillip Vance Smith, II is serving life without parole in North Carolina. He advocates for criminal sentencing reform through journalism and legislation. He is currently working toward publishing a memoir about the difficulties and consequences of activism behind the wall. His writing has appeared in HuffPost, Slate, and The North Carolina Law Review, among other publications. Read his personal essays describing the esoteric side of incarceration on his free Substack page, Prison Life Unlocked.
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