[2] Regarding his interpretations of Cole Porter, fellow cabaret pianist Michael Feinstein noted that Ross has, "an ability to create a reserve or an 'arch' quality that certain of his songs require and that eludes" other performers.

After being honorably discharged from the United States Army in 1963, he began playing piano professionally among the saloons and nightclubs of Washington, D.C. First gaining notoriety as a cabaret performer in the late 1970s during his residency at the Theatre District, Manhattan venue Ted Hook's Backstage, Ross was described as having, "boyish vivacity and skill as an accompanist [that] encouraged many stars to rise and perform...", including Ginger Rogers, Kay Thompson, and Liza Minnelli.

[5] Cabaret historian James Gavin noted, "...For four seasons Ross provided the sorts nights that an older generation of New Yorkers had grown to miss and that a substantial young audience had yet to discover.

The Oak Room would later host other cabaret artist including Michael Feinstein, Andrea Marcovicci, Susannah McCorkle, and jazz-oriented performers Diana Krall, Harry Connick Jr. and John Pizzarelli.

Ross has played alongside cabaret and jazz performers including ragtime pioneer Eubie Blake,[12] Karen Akers, Judy Carmichael, and Vince Giordano.