While Rauschenberg was no stranger to collaged found imagery, the silkscreen technique reinvigorated his artistic practice in the early 1960s. After Andy Warhol introduced him to the photo-silkscreen technique. Rauschenberg created a series of silkscreen paintings that allowed for an open-ended association of meanings through his appropriation and arrangement of mass media imagery. In Skyway, Rauschenberg wanted to communicate the frenetic pace of American culture encapsulated in the early half of the decade, particularly as represented on television and in magazines. He stated, "I was bombarded with television sets and magazines, by the excess of the world. I thought an honest work should incorporate all of those elements." He created the work in the year following the assassination of John F. Kennedy. Kennedy was a potent symbol for change, even though he was struck down only halfway through his first term as president. The image of Kennedy appears twice in the upper half of the painting surrounded by images that illustrate the ideals of American progress in the second half of the 20th century including an astronaut, the bald eagle, and a large, mechanical crane surrounded by a demolished building. The lower half of the canvas contains a repeated image of Morning Toilet of Venus (1615) by Peter Paul Rubens. The mirror within the painting expands the image into the viewer's space, mirroring the world around them as well as the world around Rauschenberg when he created the work. While the appropriated images can be read as politically and socially laden, Rauschenberg claimed he aimed to encapsulate the contemporary climate rather than comment on it, using "simple images" to "neutralize the calamities that were going on in the outside world."

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