In 1989 Loeb moved to New York, where he lived for a time with the musician Moby and worked in a variety of creative fields including graphic design and video production,[4] while honing his style in part by studying cinematic composition.

“I use transparency and pigment to emphasize something photos can't.“[10] Despite the fact that many of his contemporary peers copied photographic works wholesale, charges of copyright infringement continued to dog Loeb through the late 1990s.

[19] In 2017 he traveled to Jackson Hole, Wyoming, to capture the total solar eclipse visible from North America, using a hydrogen alpha telescope with an attached camera to observe and record the two minute and twenty-two second phenomenon.

[20] “Pushing the landscape genre into the realm of the extraterrestrial, Damian Loeb gives the nineteenth-century Romantic sublime a twenty-first-century reboot by depicting vistas that would have been inconceivable in earlier eras, such as view from airplanes and the Hubble telescope, Loeb’s glossy hyperrealist style has a distinct digital vibrancy, though his large-scale canvases call for an extended contemplation not commonly associated with digital images,” wrote art historian Robert Shane in Landscape Painting Now.

[26] In the fall of 2019, Loeb delivered a lecture at Yale University as part of his residency with their Center for Collaborative Arts and Media, exploring the culture of surveillance, in an ongoing project titled My First Algorithm.