Alumni Spotlight: Toccara Castleman

A Woodlawn native and member of the first class of Wentcher scholars, Toccara Castleman remembers falling in love with performing at a young age. In 6th grade she appeared in the play Roll of Thunder Hear My Cry at ETA theater on the city’s South Side. The play was an adaptation of the book that Toccara’s class had recently finished reading about a girl named Cassie who stands up against racial injustice. In the play, Toccara was cast as Cassie. However, in the adaptation made by her class, her character only had one line. Toccara said that she made the most of her time on stage and was able to make the audience laugh. Garnering a good reaction from the audience sparked something in Toccara. She stated that she felt at home on stage, and from that point on knew where she needed to be.

In high school Toccara continued to perform, enrolling at Curie High School, which at the time was a performing arts high school. There, she learned the meaning of balance as she was a theater major who was also a member of the rigorous International Baccalaureate (IB) program. After graduating high school, Toccara became part of the first class of Wentcher Scholars and a freshman at the University of Illinois Urbana-Champaign. In college, she started off as a Journalism major but ultimately graduated with a degree in Media Studies. While at UIUC, although Toccara did not major in theater, she still participated in various productions on campus. 

Very fond of her college experience, Toccara noted that although she was extremely focused on her academics, she made some really great friends at U of I. She also spoke about how being in the first class of Wentcher scholars helped her significantly. Toccara was thankful that the Wentcher Foundation made college accessible to her in a wonderfully supportive way. Toccara said that because of the scholarship she received from the Foundation she did not have to take out any student loans which she acknowledged put her in a unique position and placed her at a financial advantage when pursuing her post-graduation dreams. 

After college, Toccara moved to New York City where she was briefly a member of the Teach for America program in the Bronx. While in New York, she began working on her first full-length play. Describing it as a “labor of love,” Toccara told us that it took her eight years to write her play because of the complexities of the subject she tackled. The play, titled Maybe a Mexican, is set in 2020 and follows the journey of a working-class Mexican-American man who decides to run for President of the United States—asking not what he can do for his country but questioning what his country can do for him. We asked Toccara what inspired her to write this play given that her background is vastly different from the main character’s, and she said that the piece was inspired by news articles she read about the racial projection of what group the next President should represent—after the country’s first Black President was elected. Toccara said she remembers being on the train thinking to herself that perhaps it was time for a Mexican-American to run for office, and thus her idea for her play was born. Having her play workshopped in a few local theaters in New York, Toccara was able to receive feedback on her script which was really helpful for her because people from all backgrounds, especially members of the Latinx community were able to provide her with pivotal insights. Although Maybe a Mexican has not been fully produced yet, the play has already seen success, winning semi-finalist recognition in the Blue Ink Festival (2020 & 2021), an award created in 2010 to recognize new plays and playwrights. In the future, Toccara hopes to have her play premier in Chicago leading into the next presidential election. You can find more about Maybe a Mexican on the play’s website here.

Outside of successfully developing her own project, Toccara has enjoyed a bit of mainstream success as well. For the majority of her career, Toccara worked for NBCUniversal (SYFY Channel & USA Networks) as a digital marketer, site manager, editor and producer. Throughout her tenure with NBC, Toccara worked to support the success of more than 80+ original and unscripted television series, including Mr. Robot, which garnered Toccara and her colleagues a 2020 Emmy Award for Interactive Extension of a Linear Program. 

Currently, Toccara is based in Chicago working for Goodman Theatre as the Director for Digital Strategy. For the past six months she has been working in this role to create, manage and produce a comprehensive content strategy for Goodman’s Social Media platform, to increase sales, membership and engagement. It’s a role that she enjoys because she has always wanted to work in theater and the opportunity also utilizes her skills as a digital marketer. Toccara explains that it’s been an honor to work for such a pillar in the theater community.

We asked Toccara if she had any advice for scholars looking to get into the entertainment industry, and she had the best suggestion! “Take advice with a grain of salt.” Toccara went on to explain how there’s no single way to be creative, and so the best thing you can do is be selective with the advice you take. Her suggestion, “Take what you need and leave the rest.”

Outside of working for Goodman and on her play, Toccara loves to take classes! Including: tango, tap, sewing, cooking and various acting and writing courses. She most recently took a scene study class at Acting Studio Chicago. And will soon be starting a Solo Show focused acting class so that she can finish her next play. She also tells us that she’s been taking Spanish for about a year and a half and has a language partner she practices with in Mexico. Toccara also loves books citing Dominicana by Angie Cruz and Luster by Raven Leilani as one of her latest favorites. 

We are so proud of Toccara for all of her successes, and we look forward to seeing all that she accomplishes in the future!