During his childhood he had a fascination with mass media; movies, television, magazines, and comic books, which continue to influence his art.

[6] After enlarging the pictures through a projector, he and an artist assistant drew them in sizes ranging from three-quarter scale to larger than life-size.

[7] According to art critic William Wilson of the Los Angeles Times, the pictures recall nothing so much as the final scene in Ingmar Bergman's The Seventh Seal.

[9] As a consequence, in his 30s, Longo was among the most widely publicized, exhibited and collected artists of the 1980s along with the likes of Cindy Sherman and David Salle.

[12] From 1995 to 1996 he worked on his Magellan project, 366 drawings (one per day) that formed an archive of the artist's life and surrounding cultural images.

[14] To create works such as Barbara and Ralph, Longo projects photographs of his subjects onto paper and traces the figures in graphite, removing all details of the background.

After he records the basic contours, his long-time illustrator, Diane Shea, works on the figure for about a week, filling in the details.

During the late 1980s and early 1990s Longo developed a number of performance art theatre pieces, such as Marble Fog and Killing Angels, collaborating with Stuart Argabright, the guitarist Chuck Hammer and Douglas Sloan.

Menthol Wars also was part of a series of three staple-bound paperback books by Richard Prince published during 1980 by Printed Matter, Inc.. During the same period, Longo also performed with Rhys Chatham in Chatham's Guitar Trio and produced a series of slowly fading slides entitled Pictures for Music which was projected behind the musicians.

Commissioned by Italian luxury label Bottega Veneta, Longo photographed models Terron Wood and Alla K for the brand's fall/winter 2010 advertisements, evoking memories of the dancing silhouettes of his Men in the Cities series.

[23] His photorealistic charcoal drawings were featured in the exhibition Proof at the Brooklyn Museum in 2017 alongside works by Francisco Goya and Sergei Eisenstein.

[24] Longo's work from the Men in the Cities series was prominently displayed in the apartment of fictional character Patrick Bateman in the film American Psycho (2000).