[6] At the age of seven, she sang "The Bonnie Banks o' Loch Lomond" in Our Gang Follies of 1938, and played Judy Garland's character's sister in Presenting Lily Mars (1943).

"[12] In 1952, Ross met Prestige Records owner Bob Weinstock, who asked her to write lyrics to a jazz solo in a similar way to King Pleasure, a practice that would later be known as vocalese.

[8][13][14] The song, first released in 1952 (later collected on the album King Pleasure Sings/Annie Ross Sings), was an underground hit, and resulted in her winning Down Beat magazine's New Star award.

[9][13][15] In February 1956, the British music magazine NME reported that Ross's version of the song "I Want You to Be My Baby" was banned by the BBC due to the lyric "Come upstairs and have some loving".

[17] Their first, Sing a Song of Basie (1957), was to have been performed by a group of singers hired by Jon Hendricks and Dave Lambert with Ross brought in only as vocal consultant.

Over the next five years, Lambert, Hendricks & Ross toured all over the world and recorded such albums as The Hottest New Group in Jazz (1959), Sing Ellington (1960), High Flying (1962), and The Real Ambassadors (1962), written by Dave Brubeck and featuring Louis Armstrong and Carmen McRae.

Annie's Room hosted Joe Williams, Nina Simone, Stuff Smith, Blossom Dearie, Anita O'Day, Jon Hendricks, and Erroll Garner.

[19] Her adulthood film roles included Liza in Straight On till Morning (1972), Claire in Alfie Darling (1976), Diana Sharman in Funny Money (1983), Vera Webster in Superman III (1983), Mrs. Hazeltine in Throw Momma from the Train (1987), Rose Brooks in Witchery (1988), Loretta Cresswood in Pump Up the Volume (1990), Tess Trainer in Robert Altman's Short Cuts (1993), and Lydia in Blue Sky (1994).

[24] In July 2006 a one-woman play entitled TWISTED: The Annie Ross Story by Brian McGeachan premiered at The Space Theatre in London, starring Verity Quade.