Greg Kwedar’s 2023 prison drama Sing Sing champions the merits of art as a force for healing and empowerment in an era of doubt and despair. Operating as a reflection of the true events, the film is a semi-fictionalised biography that catalogues the transformative powers of the real-life ‘Rehabilitation Through The Arts’ program at Sing Sing Correctional Facility. Featuring a majority cast of ex-inmates – living testaments to the program’s success – the film is led by an electrically tender performance by Colman Domingo.The cast elevates the film into brave heights, as they toy and tinker with the audience’s heartstrings, offering us insight into the world-shaping influence of art and brotherhood.

Fixed beside this film this week isOscar Wilde’s poem ‘Ballad of Reading Gaol’ – a testament to the lives of those incarcerated. Wilde’s wordcraft has often ignited within me an undeniable appreciation for art and its many-sided faces. This poem, written during his time incarcerated at the eponymous prison, is an outstandingly gripping example of Wilde’s storytelling strength. His narrative assessment of prison life, the spiritual exile felt by those imprisoned, and the fraternity shared by prisoners, excels at sketching a bleak portrait of despair. Whilst the poem itself does little to shine any hope on the umbrous nature of incarceration, its conception and responsibility as an artistic reflection of prison life, merits it as an example of how art can salvage some respite within the worst of conditions or experiences.  

Bonded together, both the film and poem succeed as shining examples of creativity cultivated at the hands of convicts and ex-convicts. Whilst Sing Sing itself does involve the masterful involvement of creatives such as Domingo, Kwedar, and Paul Raci, its importance as an artistic text is mainly anchored within the fact that its very fabric is rooted in the involvement of those who are alumni of the program itself. 

Composed of an entourage led by the raw dynamism of Clarene ‘Divine Eye’ Maclin (who plays a fictionalised version of himself), the film is intrinsically bound together by the authentic portrayals of ex-convicts, who now embrace the remediative quarters of acting. Their influence, their craftsmanship propel the film from the safety of being a dramatic reenactment, and instead gift the film an authentic edge that is both beautiful and earnest in its visual emancipation from convention. As a ‘handmade’ production, the genuine and sincere elements of the film spill into the narrative itself, as the audience is made to experience the authenticity of rehearsals, auditioning, and stagecraft, as the prisoners band together to create something that is of their devising. 

These rough edges and sometimes comically rugged portrayals example the bravery of these men, who, despite their conditions, excel into stardom. If these elements were removed, the film itself would struggle to stand above any labels of being artificial. Through their spatial limitations, the prisoners dig deep into the centre of themselves, unearthing value that previously might have been coated beneath layers of shallow masculinity, vulnerability, and economic hardship. In their admission that they have nothing, they learn that they have everything, as they labour for an art that helps them redefine their selves. 

As a documentation of artistic struggle, the film is itself evidence that through the process of art, humanity becomes malleable and adaptable to whatever the world imposes upon it. Like the film, Wilde’s poem is a document that delivers more than a reproduction of an experience. Tracking and tailing behind the disintegrating figure of Charles Thomas Wooldridge, a murderer condemned to execution, Wilde shadows the morbid realities of those condemned. Through the exposure of this specific, historical experience, Wilde wields his talent to ensnare the reader and force them to recognise how prison life can isolate individuals and their spirits. 

Aside from the poem’s activity, its creation and purpose elevate its proportions. Wilde’s biographical experience of incrimination and institutionalisation veered his once influential and pleasure-seeking existence towards a remotely distinct period of profound depression. Imprisoned within the eponymous jail, Wilde’s struggles to adapt to his new life navigate him towards the comfort of written expression, where his concerns for the future and present can be reflected upon and revisited. Acting as a sanctuary to shield him from the fearsome pressures of prison life, the poem stands as proof that artistic creation can serve as both a shield and a means of transformation within the confines of private creation. 

As vessels, the film and poem exist as repositories for the bonded influence of art and the personal tragedy of isolation. Where prison offers limitation, art offers exploration, imagination, and the incremental chance of escape. Textually, the fact that these texts can exist evidences the ability to grant even those with nothing the chance to create and change.

Internally, Sing Sing and The Ballad of Reading Gaol crystallise around a handful of acute moments where the influence of art is active and attentive. Throughout the film, protagonist John "Divine G" Whitfield (played by Colman Domingo) undergoes great creative expansion and disarming emotional reduction. Saddled with his role as the chief creative within the program’s inner circle and the embattled position of defending his innocence through parole procedures, Whitfield is a combatant through and through. His gladiatorial resolve is mirrored  in the play performed throughout the film, where he is cast as a gladiator forced to fight for the program’s success. Whitfield tussles with fellow members of the program, sparring for their salvation despite their resistance. Like Atlas, he bears the weight of others on his shoulders, and the burden of his demons in tandem. This insurmountable struggle is only medicated through creative and artistic means. 

In the solitude of his cell, Whitfield emerges as an avid playwright, a habitual sorcerer who weaves his spells through the means of drama. Additionally, his explosively sensitive turns reading Hamlet’s famed ‘To Be or Not to Be’ soliloquy, or the closing remarks from A Midsummer Night’s Dream, showcase Whitfield's immense potential as an artist and performer. It is through these artistic occupations that Whitfield’s escape from injustice and imprisonment is made probable. 

Yet, as the film nears its conclusion, Whitfield’s struggles, his doubts, and demons arise, burying him into a distanced rage that threatens to derail the program’s efforts. Kwedar shows this, not only to offer us a ‘bump in the road’ that disarms the progression of the narrative, but to instead communicate how art can be restorative when progress is halted. Art is staged, is this moment to be a connective tissue that supports the bond shared amongst a group or community. Whitfield’s salvation ultimately lies in the fraternity that he helped build. Without Whitfield’s dedication or the reconstructive power of art, this brotherhood, this fraternity of prisoners, would be unable to collectively empower each other and resist the temptations of their criminal past. 

A repeated motif haunts the narrative with profound effect throughout Wilde’s poem. Originally couriered within Wilde’s focus on Wooldridge’s upcoming execution, the poem deftly examines how men inevitably destroy that which they love. Parallel to this concept of destruction, Wilde interrogates this dread that he, too, has destroyed that which he loves (his relationship with his family), and instead looks to rebel against destruction through his capacity for creativity. Whilst mostly the poem primarily examines prison life, the deeply personal and private troubles experienced by Wilde inspire us to recognise that the poem deals with loftier concerns. Like Whitfield, Wilde is isolated from his family, a figure burdened with the dread that he now haunts the ruins of a life destroyed. Their overwhelming fear, that little remains of their life, entrenches them within an oscillating position, where their habit for creation is often sabotaged by a history of destruction. Whereas we can find redemption in Wilde’s construction of such a formidable piece of art, his final remark resoundingly reiterates his fear that destruction rests in the hearts of all men, whether it is brutal or not:

“ And all men kill the thing they love,

By all, let this be heard,

Some do it with a bitter look,

Some with a flattering word,

The coward does it with a kiss,

The brave man with a sword.”

Moreover, Wilde deals with a cautionary tale that wards away any moral high ground. He muses that art itself cannot only be concerned with the aesthetic beauty of this world, but also the dark and destructive.

Questions have long surrounded the ‘need’ for the arts in a world that is rampantly driving towards technology and high-scale innovation. Governments might soon be reluctant to bury the hatchet when it comes to making further cuts to funding the arts, but this optimism rests on fragile ground. As the arts continue to be decimated, films like Sing Sing remind us that art is integral to every corner of society. Be it private, profound and personal or performed, art has power over our potential to be more. Sing Sing freezes over any doubts that might be raised when it comes to the influence that art can have over someone’s life. Wilde’s poem, on the other hand, trials us with increased depth. Reminding us of the sanctuary and safety that art can provide, Wilde’s poem symbolises how, in moments of severe distress, art can be a safe space to remove us from an environment that seeks to see us fail. If you doubt that art is something erasable and unworthy of support, remind yourself of those moments where your comfort has relied on art as a scaffold that separates the world from your door.