WANDA SYKES: One of the Most Celebrated Entertainers of Her Time

Wanda Sykes portraint, n.d. Photo Unknown

“I’m proud to be a woman. I’m proud to be a black woman, and I’m proud to be gay.”

TRQ: Wanda Sykes Born March 7, 1964

One of the most celebrated entertainers of her time, Wanda Sykes is an Emmy Award winner who has captured the hearts and minds of audiences worldwide using sharp wit and unapologetic humour. As the first African American and openly gay master of ceremonies for the White House Correspondents’ Dinner, she has shattered barriers and set new standards for excellence in her field. On stage, she has performed alongside Chris Rock, Regina Hall, Amy Schumer, Julia Louis Dreyfus, and Cyndi Lauper.

Beyond her comedic genius, Sykes has emerged as a tireless champion for the LGBTQ+ community, using her platform to shine a light on issues of discrimination and inequality. Through her bold and insightful commentary, she has inspired countless individuals to stand up for their rights and fight for a more just and fair society.

Sykes was born into a family of service, with her father serving as an Army colonel and her mother working in banking. Growing up in the Maryland suburbs of Washington, D.C., she developed a keen sense of the world around her, and a deep appreciation for the sacrifices her parents made in service to their country.

After completing her studies at Arundel High School, Sykes set her sights on higher education, enrolling at Hampton University, a storied institution with a rich legacy of educating African American leaders. There, she pursued a degree in marketing, honing her skills and preparing herself for a career that would take her to new heights of success and achievement.

Sykes began her career as a procurement officer for the National Security Agency (NSA), a position that placed her at the forefront of America’s national security efforts. In 1987, her first foray onto the stage was in a talent contest in Washington, where she discovered a newfound passion for making people laugh and connecting with audiences profoundly.

Despite early setbacks, including a failed second try at stand-up, Sykes remained undeterred in her quest to become a successful comedian. While working full time at the NSA, she continued to hone her craft, performing at local clubs and events on nights and weekends.

Wanda Sykes struggled for years to come to terms with her sexuality, feeling the weight of social and cultural pressures to conform to a more traditional way of life. In 1991, she married record-producer David Hall, hoping to find acceptance and validation in a society that often viewed same-sex relationships with suspicion and disdain.

In 1992, Sykes took her career to the next level, moving to New York City to immerse herself in the vibrant and competitive world of comedy. There, she found new opportunities to refine her skills and connect with audiences, paving the way for a career that would see her rise to the top of her field.

Sykes’s personal and professional lives diverged dramatically in the late 1990s, as she navigated the challenges of a failed marriage and the demands of a burgeoning career in comedy. Despite the pain and heartache of her divorce, Sykes viewed the experience as transformative and allowing her to embrace her true self and pursue romantic relationships with women.

Sykes was rapidly becoming one of the most sought-after comedians in the business, honing her skills on stages across New York City and earning critical acclaim for her writing and performances on The Chris Rock Show.

In 1999, the entertainment industry recognized Rock’s talent team members when they won an Emmy Award for Outstanding Writing for a Variety, Music, or Comedy Program. Over several years, the team earned four nominations for the prestigious award, cementing Sykes’s status as one of the most innovative and impactful writers in the business.

Sykes’s work with Rock continued into film with Chris Weitz and Paul Weitz’s Down to Earth (2001) and Pootie Tang (2001). Sykes became a fixture of the television landscape, delighting audiences with her sharp wit and impeccable timing. As well as hosting the 2002-2003 season of Comedy Central’s Premium Blend, Sykes appeared in a variety of roles on hit shows like The Drew Carey Show and Curb Your Enthusiasm. She even turned a chance encounter with sportscaster Bob Costas into a fruitful collaboration, using her quick thinking and comedic instincts to earn a recurring spot on the HBO series Inside the NFL. For her work on the show, Sykes received two Emmy Awards in 2002 and 2004.

In 2006, Wanda Sykes joined the cast of The New Adventures of Old Christine in a recurring role. Sykes’ character on The New Adventures of Old Christine married the character played by Julia Louis Dreyfus, despite both characters being heterosexual. This bold move challenged traditional gender norms and helped to open the door for a greater representation of marginalized groups on mainstream television.

That same year, she also took on the role of executive producer for her own HBO special, Wanda Sykes: Sick and Tired. Known for her sharp, incisive humour, Sykes tackled a wide range of provocative topics in the special, including politics, race, and same-sex marriage. Her unflinching honesty and razor-sharp wit made her an instant fan favourite, and cemented her reputation as a fearless performer who was unafraid to speak her mind. 

Through her participation in pride festivals, a gay cruise, and Cyndi Lauper’s True Colors Tour in 2008, Sykes established a significant following among the LGBTQ+ community. She used her platform to advocate for the community by creating a public-service announcement for the Gay, Lesbian, and Straight Education Network (GLSEN) in 2007 and voicing her opposition to California’s Proposition 8, a bill aiming to restrict marriage equality in the state, on Ellen DeGeneres’s show before the November 2008 election.

Although Sykes alluded to her heterosexual marriage during her comedy routines, she was initially perceived as an ally until she publicly revealed her sexual orientation shortly after the election.

Sykes gave an impassioned impromptu speech at a rally protesting Proposition 8 in Las Vegas, where she was performing. “I don’t really talk about my sexual orientation. I didn’t feel like I had to. I was just living my life, not necessarily in the closet, but I was living my life,” she stated. “I’m proud to be a woman. I’m proud to be a black woman, and I’m proud to be gay.”

Sykes disclosed her marriage to Alexandra (or Alex) in October 2008, but kept her wife’s privacy intact, saying, “She’s not in show business. I want her to have as much of her private life as she can.”

In April 2009, Alex gave birth to twins Olivia Lou and Lucas Claude. 

At the May 2009 White House Correspondents’ Association dinner, Sykes broke barriers as the first African American woman and openly LGBTQ+ headliner. Her daring routine took jabs at prominent figures such as Sarah Palin and Rush Limbaugh. It sparked both criticism and admiration. Sykes fearlessly standing behind her comedy recalls the bold title of her book of comedic commentary, Yeah, I Said It (2004).

In October 2009, Sykes’ HBO comedy special, I’ma Be Me, made its debut. Shortly after, in November 2009, she premiered her own talk show, The Wanda Sykes Show, on the Fox network.

Sykes often takes to Twitter to voice her political opinions. On May 25, 2021, she retweeted a photo by Evan Vucci of Gianna Floyd, daughter of George Floyd, entering the White House. On July 17, 2021, she urged her followers to support the passing of the #ForThePeopleAct in Congress and take part in the “Good Trouble Vigil” in honour of late activist and Congressman John Lewis.

Sykes has had an impressive run in recent years, starting with her starring role on the hit Netflix sitcom The Upshaws in 2021. She then co-starred at the 94th Academy Awards with Regina Hall and Amy Schumer. In January 2023, The Daily Show tapped Sykes to guest host after Trevor Noah’s departure.

Wanda Sykes has been a trailblazer throughout her career, using her platform as a stand-up comedian, actor, writer, and producer to speak out on social and political issues. From her ground-breaking appearance as the first African American and openly gay master of ceremonies at the White House Correspondents’ Dinner to her impassioned speeches at rallies protesting Proposition 8, Sykes has fearlessly used her voice to advocate for LGBTQ+ rights, racial justice, and other important causes. Her work has garnered critical acclaim and multiple Emmy Awards, and her continued success on stage and screen is a testament to her talent and unwavering dedication to making a difference.

The Wanda Sykes Show, circa 2009. Photo FOX
Wanda Sykes on the cover of Ms. Magazine, Summer 2004. Photo Liberty Media for Women, LLC
Wanda Sykes on the cover of her Yeah, I Said It book, 2005. Photo Jim Wright, Atria Books
Wanda Sykes on the cover of JET Magazine, 2004. Photo JetMag
Wanda Sykes, I’Ma Be Me Special, October 2009. Photo HBO
Wanda Sykes headshot, 2009. Photo Unknown
Wanda Sykes during stand up set, 1998. Photo Comedy Central
Wanda Sykes with Yvonne Orji for Glamour magazine, 2018. Photo Williams + Hirakawa
Wanda Sykes, What Happened… Ms. Sykes? Special, 2009. Photo ePiX
Wanda Sykes portraint, n.d. Photo Unknown

About the Authors

Troy Wise is currently a PhD student at UAL Central St Martins and teaches fashion and graphic design at London College of Contemporary Arts. His background is in marketing and is founder and co-editor of Image Amplified. He lives in, and is continually fascinated by, the city of London.

Rick Guzman earned his most recent MA at UAL Central St Martins in Applied Imagination in the Creative Industries. He currently holds two MA’s and an MBA in the New Media, Journalism and International Business fields. Co-editor at Image Amplified since its start, he lives in London, is fascinated by history and is motivated by continuing to learn and explore.


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WANDA SYKES: One of the Most Celebrated Entertainers of Her Time

WANDA SYKES: One of the Most Celebrated Entertainers of Her Time