Gilbert-Rolfe held several degrees, including a National Diploma in Painting from Tunbridge Wells School of Art (1965), an ATC from the London University Institute of Education (1967), and an MFA from Florida State University (1970).

His work is in the permanent collections of the Albright-Knox Gallery of Art, Buffalo, NY; The Getty Study Center, Los Angeles; the Hammer Museum, Los Angeles; the Los Angeles County Museum of Art; the Museum of Contemporary Art, Los Angeles; the Museum of Contemporary Art, North Miami; the Frederick R. Weisman Foundation in Los Angeles and Minneapolis; the Whitney Museum of American Art, New York; and other public, corporate and private collections.

He said he went to an exhibition at the Tate Gallery in London in 1963 to see the Pop Art that was in it but what caught his attention instead, causing him to decide he needed to go to America, were the paintings of the New York School and especially and specifically Barnett Newman's Vir Heroicus Sublimis (1951).

Rachel Kushner discussed Gilbert-Rolfe's indebtedness to Newman and Hawks and much else, going on to say that she made an “automatic and instinctive” association of his painting Hottest Part of the Day (2001) with a poem of Sappho's, and that it is her “sense that Gilbert-Rolfe had some uncanny mesh with feminine sensibilities.

Among other things, it would permit us to get closer to the sublime or sublimes that tough guys are too scared to touch.”[6] As Kushner puts it, “Gilbert-Rolfe … lays out his ante, but never knows where a painting will go.”[4] In 2010 Gilbert-Rolfe and Rebecca Norton began to work together as the collaboration Awkward x 2, making paintings together and also writing occasional blogs.

[7] Gilbert-Rolfe wrote about art and related topics, including poetry, fiction, fashion, with particular regard to its interaction with photography, digital technology, and the general state of things in art and how the present situation seems to have emerged.

In Gilbert-Rolfe’s version Winckelmann’s masculine active becomes instead androgynous transitivity, while intransitivity replaces passivity as a still entirely feminine characteristic, the feminine as intransitivity being a sign or force that stands for, or embodies, power as a kind of powerlessness.

Here and elsewhere Gilbert-Rolfe suggests that techno-capitalism and the subjectivity that accompanies it are largely made out of all that Martin Heidegger warns against and denounces in his post-war essays on technology, for example the telephone's capacity to sever the mutual dependence of space and time.

In 2015, Gilbert-Rolfe retired as a teacher from Art Center College of Design and received the title Professor/Chair Emeritus.

In addition, he worked as a Visiting Lecturer at Yale University School of Architecture from 1987 to 1989.

Lastly, since 1999, he was a Visiting Tutor at the Royal Academy Schools in London, teaching Painting.

Some of his most famous students while teaching at Art Center include: Lynn Aldrich, Lisa Anne Auerbach, Dave Hullfish Bailey, Aaron Curry, Sharon Lockhart, Steve Roden, Sterling Ruby, Frances Stark, Jennifer Steinkamp, Diana Thater, Pae White, and Jennifer West.