He began his career writing for The Village Voice before becoming the editor-in-chief of pop artist Andy Warhol's Interview magazine from 1971 to 1972 and from 1974 to 1983.

[7] As a graduate student in the Film department at Columbia University in New York, his first publications doubled as his class essays and homework assignments.

[8] In 1970, Colacello wrote a review of Andy Warhol's film Trash, which he hailed as a "great Roman Catholic masterpiece".

[10] Colacello recalled that Warhol suggested he change his name to Bob Cola, in order to sound more "pop.

For a time Colacello lived with a boyfriend, Kevin Farley, who worked at Iolas Gallery in New York.

"[14] In 1984, Colacello began writing for Vanity Fair magazine,[15] and has been a regular contributor since, writing extended profiles on a wide range of public personalities, including Prince Charles and Camilla Parker Bowles,[16] Balthus,[17] Rudolf Nureyev,[15] Liza Minnelli,[18] Estée Lauder,[19] Doris Duke,[20] and Naomi Campbell.