'Say Yes To The Dress': Emasculation of Black Men in Hollywood or Homophobia?

Author Nikki Iyayi

Hollywood's portrayal of Black men has ignited intense debate, particularly concerning representations that challenge hetero-normative gender ideas.

From Tyler Perry's Madea to Billy Porter's iconic red carpet appearances, the visibility of Black men in dresses has sparked conversations about masculinity, gender identity, and representation in the media. Through the limited binary concept that Black men are either dangerous and thuggish, or effeminate and wimpy––a liminal space was created through which Black men can be accessed palatably by society (which has its roots of subjugation in slavery), through drag. 

There is a notion that there is a right of passage for a Black man in Hollywood to achieve success, and that is through saying yes, to wearing a dress. Tyler Perry did this with the Madea franchise in the ‘00s, Eddie Murphy with Norbit (2007) and Martin Lawrence in the Big Momma’s House series (2000 - 2011). All of these men have gone on to achieve wealth, success and status in their respective careers in acting, producing and comedy. These portrayals, often featuring Black men in dresses, have sparked conversations about perceived masculinity, gender identity, and the broader implications for hetero-normative societal perceptions. Is this a progressive move towards gender inclusivity, or does it perpetuate harmful stereotypes of emasculation and homophobia?

Katt Williams

Katt Williams is one comedian who did not do it. In Katt Wiliams’ recent explosive interview with Shannon Sharpe on Club Shay Shay, which racked up 3M views in 3 days, he exposed a conspiracy that Hollywood has an agenda to put Black men in dresses. He mentioned that due to his personal boundaries, he has been able to evade this inevitability that other comedians have had to accept in order to further their careers, sometimes against their will. He speaks about the effort to emasculate Black men in film and TV, and those who go along with it will get success, and those who don’t, like Williams and Dave Chappelle, have had to progress with their careers without support from the industry. 

Dave Chapelle talks openly about being a conspiracy theorist in an interview with Oprah in 2006, and mentioned a pattern of seeing Black men in a dress at some point in their career. In his own anecdote, he refused to wear a dress when he was pressured by fellow actor, Lawrence, and other crew members on set. His resistance to this was based mainly on the fact he wanted to focus on the comedy writing and delivery, as opposed to the appearance of what he would have to wear, and how that would make him feel on a personal level. 

Kevin Hart’s Quvenzhane Wallis SNL skit in 2013, where he impersonated the then 9-year old, dressed as a pope, elicited many laughs and a raised profile for Hart. Following on from this, Hart’s career skyrocketed with an incredible five comedy sketch release the year after in 2014. Prior to this, Hart released one sketch a year from 2009 - 2013. Now in 2024, Hart has a prolific career in producing, acting and comedy, selling out shows across the world. Similar individuals who have worn dresses include the Wayans brothers, Marlon and Shawn, in White Chicks (2004), Perry, Murphy and Lawrence, and many more. 

Historically, cross dressing or drag, has been closely associated with theatre, drama and an ancestor of this is the pantomime dame. The pantomime dame embodies a female character, usually played by an older male actor. With a grandiose and hyperbolised feminine quality, the pantomime dame is a conduit for lewdness and cheap laughs during production. 

However, the concept of men wearing dresses or skirts is not new, illustrating the fluidity of cultural expression across human civilisations across history. In many African cultures, dress-like garments have been worn by men for centuries, often as part of traditional attire that reflects cultural heritage and identity. For example, in various regions of West Africa, men wear garments such as the agbada, a flowing robe-like garment with wide sleeves, or the boubou, a long robe that is often elaborately embroidered. These garments are not only functional but also serve as symbols of status, lineage, and cultural pride. Similarly, in parts of East Africa, men wear garments such as the kanzu, or in Scotland, where the kilt, a pleated, knee-length wrap-around skirt has been worn traditionally since the 18th century. 

Billy Porter

In 2019, the entertainment landscape witnessed a groundbreaking moment with Billy Porter's historic win at the Primetime Emmy Awards for his role in Pose (2018-2021). Porter's portrayal of ‘Pray Tell’ marked a significant milestone, not only as the first openly gay Black man to win in the Outstanding Lead Actor in a Drama Series category but also for challenging stereotypes and expanding the representation of Black masculinity on screen. His unapologetic embrace of gender fluidity resonated deeply, sparking conversations about the intersectionality of race, sexuality, and gender identity. RuPaul’s Drag Race (2009) is an American reality competition series where contestants battle to win a large cash prize, with the largest being $200,000––a life-changing amount of money for many worldwide. Now that the Drag Race franchise has gone global, this show has been successful in bridging the gap between hetero-normative and LGBTQ+ communities, showing the common threads of humanity, which we all share.

Balance is necessary as the inclusion of Black men in dresses is a form of resistance against homophobia and transphobia. By showcasing diverse expressions of gender identity, filmmakers and actors are advocating for acceptance and equality, fostering a more inclusive society where individuals are free to express themselves authentically without fear of judgement or discrimination. 

However, the angle within how this comes about is equally as important. It's crucial to consider the intentions behind these portrayals and the impact they have on both individuals and communities, as it brings the question whether this is a tool used to reinforce harmful stereotypes or contribute to the marginalisation of already vulnerable communities? Also, do these men wear dresses out of their own choice and free will, or are they cajoled through the expectation of a successful career?

As we continue to push for greater diversity and inclusion in film and television, it's essential to critically examine the ways in which different identities are represented and ensure that all individuals are portrayed with dignity, respect, and authenticity.