Steve Hightower (Steve Harvey) is a 1970s funk legend who is now a music teacher/vice-principal at Booker T. Washington High School on Chicago's West Side. Budget cutbacks meant Steve also had to teach drama and art, much to his surprise. Cedric Robinson (Cedric the Entertainer) is a coach at the high school, and Steve's longtime best friend. The principal of Booker T. Washington High is Steve's former classmate, Regina Grier (Wendy Raquel Robinson), who Steve affectionately calls "Piggy", because of the fact that she was overweight as an adolescent.
Steve seemingly meets his match in a pair of his students: Romeo Santana (Merlin Santana), a stylish, popular, self-absorbed ladies' man, and the equally vacuous Stanley Kuznocki, nicknamed Bullethead (William Lee Scott).
In 1997, the show introduced a new character, a secretary named Lovita Jenkins (Terri J. Vaughn), a woman who is fundamentally good in nature, but nonetheless, considerably unrefined in terms of disposition. Cedric and Lovita begin dating, and eventually marry and produce a child. The show also featured a succession of young actresses who served as female foils to Romeo and Bullethead; the longest-lasting of these was Lori Beth Denberg as the overachieving, socially inept Lydia Gutman. Rapper The Lady of Rage also had a recurring role as Coretta "The Ox" Cox, a physically massive, brutish teenaged girl in romantic pursuit of Romeo. She would also call Bullethead a "broke Brad Pitt" whenever he annoyed her, but would usually refer to Lydia as "Linda", "Lisa", or "Lucy" (correctly calling her "Lydia" only once).
Steve was part of a fictional singing group called "Steve Hightower and the High Tops," who would temporarily reunite to perform on occasion (the spelling of "High Tops" appears on a promotional poster that hangs on Steve's wall). The members consisted of Steve, T-Bone (played by T.K. Carter, later by Don 'D.C.' Curry), Pretty Tony (played by Ronald Isley of The Isley Brothers), and Clyde (played by Jonathan Slocumb). Two of their signature songs (performed several times on the show) were "When the Funk Hits the Fan" (and later on Harvey's eponymous talk show), and "Break Me Off a Piece of That Funk." Though Cedric was not an original member of the group, he usually sang with them on several events.
A few other recurring characters throughout the series included Cedric's grandmother named "Grandma Puddin'" (played by Cedric the Entertainer) and Regina's boyfriend, former NFL star Warrington Steele (played by Dorien Wilson). Kenan Thompson and Kel Mitchell appeared in several episodes as "Junior" and "Vincent." Wayne Wilderson portrayed Byron, a "bougie" type character who was a TV producer and a member of the Onyx Club (a professional men's group that Steve and Cedric tried to join). Dwayne Adway played Jordan Maddox, a professional basketball player who was briefly married to Regina before dying during their honeymoon. Ernest Lee Thomas made a couple of appearances as the Reverend who eulogized Maddox, and who married Cedric and Lovita.
There were a few recurrent gags throughout the series. For instance, Lovita had several relatives named after products or items (her brother's name was Duracell; she had cousins named "Kinko", "Bruschetta," "Clinique," and "Camay").
Steve also made several references to his well-known hot spot "The Nasty Kitty" and his favorite working girl, Bubblicious, even though the strip club is never seen. Steve's topical humor of popular culture was also another recurring gag. One example of these jokes: "When I see that woman, I'm like Shaq doing Shakespeare - I just don't know how to act!". Another recurring gag on the show was despite being a one-time famous musician in the universe of the show, Steve was always mistaken for being other famous musicians. For example, in an episode guest starring Jerry Springer, he refers to him as "That Cop from the Village People." Another episode featured singer Teena Marie, who when Steve went to introduce himself to see if she'd remember him, answers "Oh Yes! Lionel! How are you? Give my best to the rest of The Commodores." (This was in obvious reference to singer Lionel Richie.)
Though Regina blossomed into a beautiful, stylish lady, she sometimes displayed her insecurities, and was highly competitive (always displayed childlike exuberance whenever she won a trophy by yelling her signature catchphrase "Bam! In your face!", and once cheated Steve in a game of Scrabble because he played it better than she). In addition, the romantic tension between Steve and Regina eventually blossomed into a relationship, though they never kissed on the show.
A very well-known gag was Cedric's story about being from Willacoochee, Georgia, where he was raised in a one-bedroom shack. The story was never finished, the scene would change or someone would interrupt him. Cedric's love for decking out his Hyundai, which was never seen in the show, was another running gag, as well as offering to take Lovita out to dinner whenever he had a two-for-one coupon at the Sizzler restaurant.
Occasional gags referenced Bullethead's trailer park lifestyle, and Romeo's numerous names (he has used the names Romeo Miguel Jesus Pele Rojas Alejandro Santana). In one episode, he wrote all of his names on paper but never prepared his assignment, resulting in an "F". Lydia almost always displayed an obsession for her classmate/alleged lover, Arthur Rabinowitz (whom Steve referred to as "that polite Jewish boy that does his taxes"), and for her favorite entertainer, Barbra Streisand; however, she had total disdain for classmates "Heather the cheerleader" and "Jennifer the cheerleader". One other gag was that teachers would refer to a student (amongst themselves) because of a condition or appearance ("Helmet Boy" for wearing a special helmet in gym class; "Au Natural Girl" for having a strong body odor, and "Firestarter" for one kid who kept setting items on fire).Steve Harvey – Steven "Steve" HightowerCedric the Entertainer – Cedric Jackie RobinsonMerlin Santana – Romeo SantanaWilliam Lee Scott – Stanley "Bullethead" KuznockiWendy Raquel Robinson – Principal Regina Grier-MaddoxTerri J. Vaughn – Lovita Alizé Jenkins-Robinson (1997–2002)Tracy Vilar – Sophia Ortiz (1996–1997)Netfa Perry – Sara (1996–1997)Ariyan A. Johnson – Aisha (1997–1998)Lori Beth Denberg – Lydia Liza Guttman (1998–2002)Kel Mitchell – Vincent (1996–1999)Kenan Thompson – Junior (1996–1999)T. K. Carter – T-Bone (1996–1999)Ronald Isley – Pretty Tony (1996–2001)Jonathan Slocumb – Clyde (1996–2001)The Lady of Rage – Coretta "The Ox" Cox (1997–2000; credited during season 4 episodes as "Robin Yvette")Wayne Wilderson – Byron (1998–2001)Dorien Wilson – Warrington Steele (1998–1999)Samm Levine – Arthur Rabinowitz (2001)Don "D.C." Curry – T-Bone (1999–2001)Dwayne Adway – Jordan Maddox (2000)Teena MarieMeagan GoodJerry SpringerBow WowJermaine DupriTeddy RileySnoop DoggSean CombsKim FieldsIsabel SanfordJudge Greg MathisAntonio FargasBusta RhymesBrian McKnightNikki CoxBoris KodjoeGabrielle UnionBumper RobinsonAdrian ZmedJenn LyonJa'net Dubois
In 2001, Harvey decided to pursue other projects. He wished to end the show after the fifth season, but at the insistence of the WB network, reluctantly filmed a 13-episode sixth season.
The series ended with Regina mulling over a job offer to be a principal at a private school in California. Steve, who doesn't want Regina to go, acts supportive despite his feelings. Regina ends up taking the job; with encouragement from Lydia, Bullethead, and Romeo, Steve decides to go after her to reveal his true feelings. Lydia, Romeo, and Bullethead have all graduated by the series' finale. Meanwhile, Cedric and Lovita win the lottery and Lovita goes into labor (Terri J. Vaughn's real-life pregnancy was written into the show that season).
On November 9, 2002, nine months after the show ended, Merlin Santana was shot in the head and killed while sitting in his friend's (Brandon Adams) car in South Central Los Angeles, California. He was 26 years old. The reason for his death is that the killer's girlfriend falsely stated that Santana tried to rape her. The episode of The Steve Harvey Show immediately following Santana's death was dedicated to his honor.
The series was first distributed to syndication to WB, FOX, UPN, and independent affiliates in the United States by Columbia Tristar Television Distribution in September 2000, and remained airing in broadcast syndication in some U.S. markets on various local stations (such as WCIU and Me-TV in Chicago) as late as 2008. From 2000-2005, reruns aired on New York's UPN station, WWOR-TV. From 2014-June 2016, After Bill Cosby's allegation, The Cosby Show reruns were replaced on WPIX by reruns of The Steve Harvey Show. The show has started airing again in syndication as of 2015.
The series aired on BET until March 2009, and was on TBS in the United States until September 24, 2011, UK Channel Trouble. It was broadcast on Ion Television until March 16, 2009.
In 2003, Sony Pictures released The Best of the Steve Harvey Show, Vol. 1, on Region 1 DVD. The disc features five episodes of the series.