In addition to longstanding work on the CBS drama "Wiseguy" from 1988-1990 and other series (including "Miami Vice" and "21 Jump Street"), Iscove worked extensively in made for TV films, managing to turn in movies of the week that were visually accomplished and dramatically compelling, despite having hopelessly cliched titles like CBS' "Breaking the Silence" (1992) and "Dying to Love You" (1993). The small screen offered Iscove the opportunity for consistent work, where he proved an inventive director, impressing with his masterful use of the limited resources. He moved into producing as well as directing in the 1990s, and took on varied projects, from the series of Janek detective TV-movies (1990-1994) starring Richard Crenna to a spate of fact-based personal horror stories like the domestic abuse chronicle "It Was Him or Us" (CBS, 1995) and even entries like the sci-fi disaster film "Without Warning" (CBS, 1994,). He tried his hand at series again, with co-producing and directing credits for the short-lived edgy drama "Profit" (Fox, 1996). The following year, his revisionist, multicultural take on the musical "Rodgers & Hammerstein's Cinderella" captured a wide audience and earned the director and producer attention and an Emmy nod.
Having already racked up film credits as choreographer of Norman Jewison's 1973 big screen adaptation of "Jesus Christ Superstar" and 1976's "The Duchess and the Dirtwater Fox", Iscove made the move to feature directing in 1999 with "She's All That", a roundabout modernization of "Pygmalion" for the high school set. More heartfelt than the lowbrow slapstick brand of comedy popular at the time and more fun than the heavy-handed John Hughes 1980s teen fare, "She's All That" was an auspicious debut, a box office success that received a fair measure of critical acclaim and set the bar for the countless teen comedy releases to come. The presence of hip-hop princess Lil' Kim and R&B heartthrob Usher added credibility, and an up-to-the-minute soundtrack made the film all the more attractive. Iscove's background in choreography obviously influenced his direction, shown not only in the film's two uncharacteristic but effective dance numbers, but also through the fluid motion of the camera throughout the film. One particularly impressive visual effect showcased an inspired transition between real and fantasy life, wherein Zack (Freddie Prinze Jr.) is seamlessly transported from the front lawn of school to poolside at spring break. The following year Iscove returned with "Boys and Girls", a similarly hip but sweet look at youthful relationships, this time set in college. The film reteamed Iscove with Prinze, and the two proved a good match. While the young actor rated high on the hot meters in the interim, Iscove was able to elicit a higher caliber performance from the young actor than he had given in some of his other projects. Co-starring fellow up and comers Jason Biggs and Claire Forlani, and marking the big screen debut of R&B diva Monica, the film was surrounded by hype-free buzz that should have appealed to its target audience. While on paper it might have seemed that Iscove had found a winning formula, "Boys and Girls" had to be ranked as a dismal failure.
In addition to this notable film and television work, Iscove was director and choreographer of the revival of "Peter Pan" starring Sandy Duncan, a captivating Broadway event that enjoyed a 1979-1981 run.