[3] In 1898 Kuuskemaa began performing as a stage actress with the song and drama society called Estonia, founded in 1865.

In 1906, the society became the basis for the professional theatre called Estonia, founded by the directors and actors Paul Pinna and Theodor Altermann.

[6] Her first performance with the Estonia Society was the role of Tiina in a production of Wilhelm Mannstädt's The Milk Maid of Schöneberg; adapted into Estonian as Ilumäe piimatüdruk ("The Milk Maid of Ilumäe") in 1898. Notable roles throughout her career at the Estonia Theatre include those in productions of such varied authors and playwrights as: Shakespeare, Richard Voss, Minna Canth, Hermann Sudermann, Teuvo Pakkala, Henrik Ibsen, Maxim Gorky, Carl Zeller, Anton Chekhov, Henryk Sienkiewicz, Leo Tolstoy, August Kitzberg, Hugo Raudsepp, Eugene O'Neill, Eduard Vilde and August Jakobson.

In 1947 she appeared in the Soviet Estonian-language drama Elu tsitadellis (Life in the Citadel) directed by Herbert Rappaport for Lenfilm, based on the 1946 play of the same name by the Estonian author and communist politician August Jakobson.

[11] Elu tsitadellis was the first post-World War II Estonian feature film following the annexation of Estonia into the Soviet Union.

The film ends with jubilant Estonians celebrating their "liberation" and inclusion into the Soviet Union and accepting communist ideology.

[14] In 1961, she appeared in the role of Mari in the Egon Rannet penned and Ilja Fogelman and Reet Kasesalu directed color musical comedy film Laulu sõber (Friend of Songs), again set against the backdrop of a collective farm.

In 1980, a 100 x 50 centimeter bronze memorial plaque was placed on her former residence at J. Poska St. 10 in Tallinn which reads, "Here lived in the years 1953–1966 Estonian SSR Honoured artist Betty Kuuskemaa."