Based on the August 23, 1956, Princeton Leader, a small-town Kentucky weekly, this drawing may well be Warhol's first work to include headlines. The artist transcribed selected articles from the front page, but with important changes. Under the headline "Local Man Completets [sic ] Apprenticeship as a Plumber, Steam Fitter," Warhol humorously inserted the name of his friend, Charles Lisanby, in place of the real subject. A theater and CBS television professional in New York, Lisanby hailed from an upper-class family and probably never wielded a plumber's wrench. Thus, this drawing offers a glimpse of Warhol's keen awareness (as a child of poverty himself) of the social stratification in 1950s America.
Taking its inspiration from the New York Post of November 3, 1961 [left], A Boy for Meg  is the artist's first use of a headline in a painting. The second painting of the same subject shows Warhol's stylistic transformation in the span of just a few months. He abandoned his more expressive, clearly hand-rendered style in favor of the slick, machinelike aesthetic for which he would become famous. With the aid of an opaque projector that enlarged and projected the newspaper source, Warhol carefully traced the images and lettering, eliminating signs of his own hand.
"Fate Presto" (Italian for "hurry up") was the headline for the November 26, 1980, Naples daily, Il Mattino ("The Morning"), on which Warhol based these three silkscreens. With this work Warhol returned to the front page of the newspaper as source material after a more than ten-year hiatus. The original headline urged a quick response following a catastrophic earthquake in the Neapolitan region. Warhol did not crop or edit this source material as he did for most of his headline works; he varied the tone and expanded the size, creating monumental canvases that echo the scale of the disaster and loudly, repeatedly call for action. Following Fate Presto, Warhol made a group of socially conscious headline paintings.
Keith Haring (1958–1990), well known for his calligraphic style of graffiti art, was a "Warhol baby," belonging to a generation that venerated the artist they called "Papa Pop." Together the two artists painted several canvases that featured headlines about their friend, the young singer Madonna. This suite of paintings based on the July 9, 1985, New York Post refers to the media frenzy that ensued after nude photographs of Madonna, taken years earlier, were sold by the photographer and published in Penthouse and Playboy. Three works from the collaboration appropriate the metro edition's headline "Madonna: 'I'm Not Ashamed"; an equal number of paintings feature the tabloid's late edition headline, "Madonna on Nude Pix: So What!"
Warhol and Haring replaced the original photograph in the late edition source (a young woman wearing a tank top and "Staying Cool") with a photograph by Haring of Madonna and Sean Penn, who would marry later that summer. As Warhol noted in his diary, less than two weeks before the wedding: "I want to do a Madonna headline—the Post one: 'MADONNA ON NUDE PIX—SO WHAT?'—and use a photograph of her from a different day that would fit right in, but Keith wants to use a photo he took of her and Sean Penn. Which is kind of grey. But I'll do it both ways. We're doing a painting together for her wedding present."