Today marks 30 years since The Steve Harvey Show premiered on August 25, 1996. The WB sitcom introduced viewers to Steve Hightower, a former funk musician who finds a new career teaching music at Booker T. Washington High School on Chicago’s West Side. The series ran for six seasons before airing its final episode in 2002.

Steve Harvey led the cast as Hightower, whose new profession put him alongside his longtime friend Cedric Robinson, played by Cedric the Entertainer. Wendy Raquel Robinson starred as principal Regina Grier, Steve’s former classmate and eventual love interest. Terri J. Vaughn joined the series as school secretary Lovita Jenkins, while Merlin Santana became a fan favorite as Steve’s student and mentee Romeo Santana.

During its 122-episode run, The Steve Harvey Show also welcomed an impressive list of guest stars. Snoop Dogg, Meagan Good, Gabrielle Union, Busta Rhymes, Kenan Thompson, Kel Mitchell, and the iconic Ronald Isley all made appearances on the series. The show also earned several NAACP Image Awards during its run, including three wins for Outstanding Comedy Series. Harvey, Cedric and Vaughn received individual honors for their performances as well.

Three decades later, several members of the cast have gone on to build lasting careers in entertainment, while others are remembered for the characters they brought to Booker T. Washington High.

Take a look back at the cast of The Steve Harvey Show, then and now.

Steve Hightower

A former 1970s funk star, Steve Hightower trades life onstage for the classroom when he takes a job teaching music at Booker T. Washington High School on Chicago’s West Side. He later becomes the school’s vice principal. His past as a performer frequently finds its way into his lessons, while his job puts him alongside longtime friend Cedric and former classmate Regina.

Steve Harvey

Harvey was already a major name in comedy when The Steve Harvey Show ended in 2002, and his career continued to grow afterward. He launched The Steve Harvey Morning Show and became the longtime host of Family Feud. His 2009 bestseller, Act Like a Lady, Think Like a Man, was later adapted into a hit film. Harvey has also earned seven Daytime Emmy Awards, two Marconi Awards and 14 NAACP Image Awards during his decades in entertainment.

Cedric Jackie Robinson

Steve’s best friend works alongside him at Booker T. Washington High School, where Cedric serves as a coach. Often caught up in Steve’s schemes, he provides a comedic counterpart to his longtime friend throughout the series. His personal life also becomes an important part of the show after he begins dating school secretary Lovita Jenkins, whom he eventually marries.

Cedric the Entertainer

Cedric the Entertainer continued the run he began during the 1990s with major roles on television and in film. Following The Steve Harvey Show and The Original Kings of Comedy, he became a familiar big-screen presence as Eddie in the Barbershop franchise and lent his voice to several animated projects. He later starred in The Soul Man before leading the CBS sitcom The Neighborhood from 2018 to 2026. In 2019, Cedric received a star on the Hollywood Walk of Fame.

Romeo Miguel Jesus Pele Santana

Romeo is one of Booker T. Washington High School’s most confident students, with a sharp wardrobe and an even higher opinion of his appeal to women. He develops a close relationship with Steve, who becomes a mentor to him during his high school years. Romeo’s personality and frequent attempts to impress his classmates made him one of the sitcom’s standout student characters.

Merlin Santana

Before playing Romeo, Merlin Santana had already appeared on television as Stanley, Rudy Huxtable’s admirer on The Cosby Show. He later added credits including Moesha, NYPD Blue, JAG and Play’d: A Hip Hop Story. Santana’s career was cut tragically short when he was killed in Los Angeles in 2002. He was 26 years old.

Principal Regina “Piggy” Grier-Maddox

Regina Grier begins the series as principal of Booker T. Washington High School and Steve’s former classmate. Their history makes his arrival particularly complicated since Steve teased her when they were teenagers. Their bickering becomes a recurring part of the series, but the relationship gradually changes. After years of sparring, Steve and Regina eventually become romantically involved.

Wendy Raquel Robinson

Robinson followed The Steve Harvey Show with one of her best-known roles as sports agent Tasha Mack on The Game, a character she played during the show’s original run and subsequent revival. Her television résumé also includes The Chi, where she appeared as Riley Dalton. Robinson won the NAACP Image Award for Outstanding Actress in a Comedy Series in 2014 for her performance on The Game.

Lovita Alizay Jenkins-Robinson

Lovita arrives during the second season as Booker T. Washington High School’s new secretary and quickly establishes herself as one of the office’s biggest personalities. Her romance with Cedric becomes a major storyline as the series progresses. The pair eventually marry, turning their relationship into another source of comedy at the school and giving Cedric a life outside his friendship with Steve.

Terri J. Vaughn

Vaughn’s performance as Lovita earned her three NAACP Image Awards for Outstanding Supporting Actress in a Comedy Series. She went on to appear in sitcoms including All of Us and Meet the Browns while expanding her work behind the camera as a director and producer. In 2025, Vaughn created, produced and starred in the Netflix political comedy Miss Governor, adding another chapter to a television career spanning three decades.

Read the original article on Essence.