In his third teaming with Lumet and his eighth and last collaboration with director of photography Boris Kaufman, Sylbert, working entirely within the studio, created the poetic backdrop for "The Pawnbroker" (1965), a strikingly photographed black-and-white journey through the mind of a Holocaust survivor living in Harlem. Building both the concentration camp and the pawnshop, he carried the grill wire as a prison metaphor from one to the other throughout the film and approximated the look of Italian neorealism to the point where people believed the picture had been made on the street. The following year he earned his first Oscar win for his claustrophobic sets (a roadside bar and the home of a college professor) on Mike Nichols' feature directing debut, "Who's Afraid of Virginia Woolf?", another super black-and-white movie (shot by Haskell Wexler) inaugurating a seven-picture association with that director. For Nichols' "The Graduate" (1967), he installed an elevator shaft in order to capture Dustin Hoffman walking down a flight of stairs without cutting. Perhaps the best of his other films with Nichols was the very symmetrical "Carnal Knowledge" (1971), designed like chamber music for four voices.
Sylbert copied apartments from NYC's Dakota to scale on sound stages for "Rosemary's Baby" (1969), his first film with director Roman Polanski. Using bolts instead of nails to fasten the sets enabled the production team to pull the walls in and out as often as necessary (without destroying them), thereby facilitating shooting. He scored an even bigger hit with Polanski's "Chinatown" (1974), a story revolving around water rights in the Los Angeles area, set during a 1937 draught. There are no clouds in Sylbert's sky, the buildings are bleached-out bone white and the color green becomes almost a symbol of power and corruption. He also raised all the buildings slightly above the eye level of private eye Jake Gittes (Jack Nicholson), who literally has an uphill climb to solve the case. In "Shampoo" (1975), his first picture with Warren Beatty as writer and producer, he repeated the latticework from Beatty's beauty parlor and Goldie Hawn's apartment in the rich person's house and then the tennis scene in an effort to unify the totally artificial world. Lots of mirrors emphasized the narcissism in the film, and to get the picture's soft and dreamy feel, cameraman Laszlo Kovacs exposed 10 percent of the negative before shooting.
In a totally unprecedented move, Sylbert replaced Robert Evans as head of production at Paramount in the mid-70s and showed he had a good eye for off-beat material, making a hit of "Looking for Mr. Goodbar" (1977) and optioning books like "A River Runs Through It" and "Interview with a Vampire" that would not see the silver screen for more than a decade. Hollywood was changing fast, however, and he was out of place among the new generation of execs with their fast food approach to manufacturing product. According to his assistant Don Simpson, Sylbert's attitude of "I'm the best art director alive. If it doesn't work out, so what" (Premiere, December 1993) didn't sit well with the suits, and he vacated the executive suite in 1978. After the undistinguished "Players" (1979), he reteamed with Beatty on the monumental "Reds" (1981), Beatty's directorial debut more than a decade in development. Two years in the making and shot on four continents, it was just the tonic Sylbert needed, earning him a fourth Oscar nomination for his detailed period work spanning the Pacific Northwest, Cape Cod, New York City and revolutionary Russia. By all rights he should have won the Oscar (Beatty did as director), but when his design lost out to "Raiders of the Lost Ark", he resolved to persevere in the presence of what he called "the stupidest generation in living memory."
Sylbert has bridged the gap between theatrical directors like Kazan, Lumet and Frankenheimer who favored a stationary camera to explore the emotional dynamics of the narrative and film school acolytes embracing the showier "Look at me" style advanced by boy genius Orson Welles. "The first film school director I ever ran across was Francis Coppola. We were standing on a set, and he said to me, 'This is going to be the Kurosawa shot.' I had never heard anybody say that in my life." (Premiere, December 1993). Despite his preference for directors who do not call attention to themselves, he garnered an Oscar nomination for Coppola's period gangster musical drama "The Cotton Club" (1984) and subsequently collaborated with Brian De Palma on the more contemporary "Bonfire of the Vanities" (1990) and "Carlito's Way" (1993). Winning a second Oscar for the cartoon strip primary colors of Beatty's "Dick Tracy" (1990), he proved he could keep pace with his changing profession, designing 45 mattes when he had only done one matte before in his life. Sylbert reasserted the importance of the production design in the era after the studio system fell apart, showing that a true artist needed more than a real-estate license and a facility for fluffing pillows. Taking time from his busy fishing schedule, he continued to work crafting the detailed and appropriate settings for the noirish "Mulholland Falls" (1996, in which he had a cameo as a coroner) and the romantic comedy "My Best Friend's Wedding" (1997). That same year, Sylbert recreated several blocks of Beijing, China in astonishing detail on seven acres near Los Angeles' airport for Jon Avnet's drama "Red Corner". Still active at a time when others might think of retiring, he crafted the meticulous settings for "In the Boom Boom Room" (lensed 2000), adapted from David Rabe's play about a go-go dancer in the late 1960s.