A relatively late starter, Schiff racked up an impressive number of credits quickly into his career, landing increasingly larger roles in film, and becoming a familiar face due to his prolific guest work on television, in addition to regular roles on the series "Relativity" (ABC, 1996-97) and "The West Wing" (NBC, 1999- ). The balding actor's realistic, average looks, sad eyes and world-weary demeanor made him an especially believable frazzled Everyman, a role that he would play masterfully in several film and television productions.
After honing his craft in downtown New York City theater productions, Schiff landed a role in the independent short "Arena Brains" (1987), directed by Robert Longo and co-starring Ray Liotta and Eric Bogosian. He moved to Los Angeles and joined Tim Robbins' acclaimed Actor's Gang, racking up more stage credits before making his feature debut with a starring role in the independent gangster comedy "Medium Straight" (1988), but soon moved on to smaller roles in bigger films, including a 1990 appearance in "Young Guns II". In 1992, the actor appeared in several features, including such blockbuster fare as "The Bodyguard" and the popular biopics "Malcolm X" and "Hoffa". Schiff continued to rack up feature credits, and moved up to supporting roles in 1996's "City Hall" and "The Arrival". The following year, in addition to acting in the features "Touch" and "Volcano" he co-starred in "The Lost World: Jurassic Park", playing Eddie Carr, an equipment specialist outfitting the research team led by Jeff Goldblum's Ian Malcolm. While Carr meets his end relatively early on in the film, Schiff's multifaceted portrayal was one of the more engagingly true-to-life aspects of Spielberg's fantastical sequel, and audiences especially responded to his efforts and struggle. In 1998, Schiff had supporting roles in "Deep Impact" and "Dr. Dolittle", and portrayed the financially successful brother of Danny DeVito's elevator operator character in "Living Out Loud". The following year, Schiff could be seen in the romantic comedy "Forces of Nature", and additionally starred in the independent New Zealand production "Heaven", starring opposite Martin Donovan as a sleazy strip club owner.
The actor's work in television was comparably prolific, guesting on many popular series and co-starring in several TV-movies. Schiff made his longform debut with 1989's "Trenchcoat in Paradise" (CBS) and was featured the following year in HBO's "Korman's Kalamity", an installment of the "Tales From the Crypt" thriller series. Roles in the NBC true crime dramatizations "Till Death Do Us Part" and "Cruel Doubt" followed in 1992. Schiff broke into series television with guest work on the acclaimed dramas "L.A. Law" (NBC) and "Picket Fences" (CBS) in 1992 and took roles in the sitcoms "Murphy Brown", "Love & War" (both CBS) and "The John Larroquette Show" in 1994. 1995 saw him take on a memorable guest role as Vartan Illiescu, a malcontent immigrant and suspected terrorist bomber, on the highly-rated police drama "NYPD Blue" (ABC). Schiff also did guest stints on the popular medical dramas "ER" (NBC) and "Chicago Hope" (CBS) in 1996, the same year that he was featured in the CBS space race TV-movie "Special Report: Journey to Mars". That fall, Landing a regular role on the critically acclaimed romantic drama "Relativity" he was cast as Barry Roth, a salesman and the emotionally detached patriarch of the less posh of the two families featured on the series. The role offered him some powerful if limited screen time, and he again showed his proficiency for making somewhat unlikable characters come across as sympathetic people with basic human weaknesses. Despite glowing reviews, the series failed to grab a significant audience and was all too quickly canceled. Schiff wasted little time getting back onscreen, though, and could be seen in ABC's 1998 remake "The Taking of Pelham One Two Three", playing Mr. Green (the role originated by Martin Balsam), a disgruntled former subway employee who masterminds the hijacking of one of the system's trains. Again, Schiff more than capably evinced a good man gone awry, showing through his eyes the volatility of someone pushed past his limit, while making the audience understand and identify with the character. That same year he took roles in the HBO political satire telefilm "The Pentagon Wars", starring Kelsey Grammer and guested on episodes of David E Kelley's legal series "The Practice" (ABC) and "Ally McBeal" (Fox). Schiff returned to series television with a regular role on NBC's "The West Wing", a Washington, DC set ensemble drama, co-starring such luminaries as Martin Sheen (as the President) and Rob Lowe. The actor brought a playful cynicism to his characterization of White House communications director Toby Ziegler, an overworked and slightly shaken man who battles his anxiety-laden profession with a dose of dry humor. As Ziegler, Schiff earned another Emmy nomination for Outstanding Supporting Actor In A Drama Series.