Whitmore made his film-making debut by writing and directing The Walking Dead (1995), chronicling the lives and mission of four African-American soldiers in Vietnam, which drew on his experiences in the Marine Corps.
Thereafter he wrote and executive-produced Fled (1996), an action picture starring Laurence Fishburne and Stephen Baldwin as two prisoners on the lam to find a hidden cache of cash and incriminating computer evidence that would bring down the Cuban Mafia.
The first Lockdown (2000), starring Richard T. Jones, Gabriel Casseus and De'Aundre Bonds as a group of friends unjustly imprisoned, tracks the gritty dissolution of their innocence and friendship behind bars.
In 2004, after completing a rewrite of the Get Shorty sequel entitled Be Cool, Whitmore wrote, produced and directed the Screen Gems film, Doing Hard Time (2004), starring Boris Kodjoe, Michael K. Williams, Giancarlo Esposito and Sticky Fingaz.
Next, Whitmore completed a trio of book adaptations, the independent feature film True to the Game directed by him, starring Columbus Short, Nelsan Ellis, Jennifer Freeman, Nafessa Williams, Andra Fuller, Draya Michele and Vivica Fox, based on the popular Teri Woods novel of the same name.
The film follows the humorous, sarcastic and sometimes harsh, talk radio host, Dominique the Dame, as she brings to the forefront America's contemporary views on race, sex, drugs, religion and technology.
It stars Jasmine Carmichael, Michael Beach, London Brown, Macy Gray, Roger Guenveur Smith, Casper Van Dien, Robert Ri’chard and Loretta Devine.
Whitmore penned the original screenplay Hello (2022), about an emotionally unavailable flight attendant who meets a potential love interest and later finds out that her perfect guy has ulterior motives— starring Eva Marcille and Charlie Weber.