In 1992 Kass began The Warhol Project. Using Andy Warhol’s technical and stylistic language to represent figures in many cases no less iconic, Kass nevertheless turned Warhol’s ambivalent relationship to popular culture on its head by choosing subjects that had an explicitly personal and political relationship to her own cultural interests. Kass painted artists and art historians that were her “heroes” in the vein of Warhol’s celebrities. Her My Elvis series speaks to gender and ethic identity by replacing Warhol’s Elvis with Barbra Streisand from Yentl: a 1983 film in which Streisand plays a Jewish woman who dresses and lives as a man in order to receive an education in the Talmudic Law. In My Elvis, Kass states her concerns about gender relations, promotes feminist advocacy in society, and directly challenges patriarchy.

Kass’s Self Portraits as Warhol nod to the act of drag performed in her all appropriation of Warhol’s work (Blue Deb, 2000).

In The Jewish Jackie Series (1992–93), Kass borrowed Warhol’s checkerboard-like compositions and inserted in the rectangles repeated Barbra Streisand (a photograph of whose head in profile with the nose held high) in place of his Jackies, Marilyns, or Judys.

In 2002, Kass began a new body of work, Feel Good Paintings for Feel Bad Times, inspired, in part, by her reaction to the Bush administration. These works combine stylistic devices from a wide variety of post-war painting, including Ellsworth Kelly, Frank Stella, Jackson Pollock, Andy Warhol, and Ed Ruscha, along with lyrics by Stephen Sondheim, Laura Nyro, and Sylvester, among others, pulling from popular music, Broadway show tunes, the Great American Songbook, Yiddish, and film. The paintings view American art and culture of the last century through the lens of that time period’s outpouring of creativity that was the result of post-war optimism, a burgeoning middle class, and democratic values. Responding to the uncertain political and ecological climate of the new century in which they have been made, Kass’s work looks back on the 20th century critically and simultaneously with great nostalgia, throwing the present into high relief. Drawing from the divergent realms of art history, popular culture, political realities, and her own political and philosophical reflection, the artist continues into the present the explorations that have characterized her paintings since the 1980s in these new hybrid textual and visual works.

Deborah Kass has recently declared her support for Democratic presidential contender Hillary Clinton with a bold, Andy Warhol-style artwork. Under the face of Donald Trump, Kass has scrawled the words “Vote Hillary.” The work mimics Warhol’s iconic screenprint Vote McGovern (1972), where the title words, urging viewers to support Democratic presidential nominee George McGovern, appear under the face of Republican incumbent Richard Nixon. Vote Hillary was produced to raise funds for the Clinton campaign, along with another edition by her fellow renowned artist and Hillary supporter, Chuck Close.