Whitaker played a kindly plastic surgeon in "Johnny Handsome" (1989), and the actor's heavy-lidded, unhurried delivery suggested the naiveté of his Mama's Boy character in "A Rage in Harlem" (1991) and the skeptical intelligence of his insurance investigator in "Consenting Adults" (1992). All three projects showed how easily he could rise above otherwise bland material. He displayed a mesmerizing depth in "Diary of a Hitman" (1991, released in the USA in 1992), the feature directing debut of acting coach Roy London. Hired to knock off the wife and child of a born-again commodities broker who claims his wife is a drug addict and the infant crack baby not his, Whitaker goes about saving the intended victim (and himself) when he discovers the broker lied in this modest, expertly-acted indie. He was also quietly, irresistibly sympathetic as a British soldier kidnapped by the IRA in Neil Jordan's highly praised "The Crying Game" (1992).

The unexpected commercial success of that film led to increased interest in Whitaker's long-form directorial debut (he had previously directed music videos), "Strapped" (HBO, 1993). Filmed on location in Brooklyn's notorious Fort Greene district, the gritty urban drama screened at various international film festivals and earned the director's award for best first feature in Toronto. Deluged with offers to direct, Whitaker remained a familiar face on screen while pondering his filmmaking future, segueing effortlessly from Hollywood genre fare, both big-budget ("Blown Away" 1994; "Species" 1995) and small ("Body Snatchers" 1993). His ability to evoke audience empathy continued undiminished as he affectingly portrayed physically and mentally maimed fathers in "Jason's Lyric" (1994) and "Smoke" (1995). Admirably unafraid to play gay characters, Whitaker also fared well as a down-to-earth designer in Robert Altman's misfired satire, "Ready to Wear (Pret-a-Porter),” and returned to the world of jazz as trumpeter Buddy Chester, stricken with a fatal brain tumor in Showtime's "Lush Life" (both 1994).

Whitaker chose to make his feature directing debut with "Waiting to Exhale" (1995), the Black female ensemble drama adapted from Terry McMillan's best seller. Boasting a large cast headlined by Whitney Houston and Angela Bassett, the film opened to mixed reviews – mostly complaints about the episodic nature of the story – and healthy box office. He returned to the other side of the camera as John Travolta's best friend in "Phenomenon" (1996) but was back in the director's chair for "Hope Floats" (1998), unable to keep the leaky craft starring Sandra Bullock from sinking. Though similar to "Waiting to Exhale" in its story of a character trying to regain belief in herself, Whitaker's sophomore effort was far less compelling, and Bullock (who also executive produced) had very little help from her mostly muted and wooden fellow actors. Although he admittedly prefers directing to acting, the demand for him to do the latter has kept him primarily in front of the camera since "Hope Floats,” though he did executive produce and helm a busted ABC pilot "Black Jaq" in 1998.

Whitaker's school security guard ("a $5 cop with a $50 a