In his early acting career he performed with various theatre troupes in Northern California from 1913 to 1915 and was often seen in outdoor amphitheaters in public parks such as the Cushing Memorial Amphitheatre on Mount Tamalpais and the Forest Theater in Carmel.
In 1916 he toured in John E. Kellerd's Shakespeare troupe, and then settled in New York City where he trained under George Arliss as a member of The Theatre Workshop in 1916–1917.
His professional debut on the New York stage occurred on November 15, 1917 when he had roles in two one act plays that were performed for the grand opening of the Greenwich Village Theatre (GVT).
In 1921 he made his Broadway debut at the 48th Street Theatre as King Stefan in Gabriela Zapolska's Sonya (original foreign language title Der Zarewitsch).
He appeared in more than 40 productions on Broadway over the next 45 years; notably creating parts in original plays by George Bernard Shaw, Eugene O'Neill and John Galsworthy, and appearing in the original casts of musicals created by composers Irving Berlin, George Gershwin, Cole Porter, Richard Rodgers, Frederick Loewe, and Rudolf Friml.
[9] In his early career Macauley performed with the theatre troupe of Garnet William Holme (1873–1929) in Northern California; often appearing in amphitheatres in National Parks and other natural settings.
[10][11] Some of his repertoire with this troupe included Petruchio in The Taming of the Shrew, Nick Bottom in A Midsummer Night's Dream, and the title role in Rip Van Winkle.
[10] In 1914 he performed the role of the chamberlain Parvatayna in Kalidasa's Shakuntala at the Cushing Memorial Amphitheatre on Mount Tamalpais,[12] and returned as Rip Van Winkle in 1915.
[21] Other roles he performed at the GVT included King Duṣyanta in Kalidasa's Shakuntala (1919),[22] Thomas Houlihan in Lennox Robinson's The Lost Leader (1919),[23] and Norbert in Jacinto Benavente's The Passion Flower (1920).
[2] In 1921 Macauley performed at Broadway's 48th Street Theatre as King Stefan in Sonya, an English language adaptation of Gabriela Zapolska's Der Zarewitsch that was translated from the original Polish by Alexander Wyckoff.
[27] On December 28, 1923 he originated the role of the Inquisitor, Brother John Lemaître, in the world premiere of George Bernard Shaw's Saint Joan at the Garrick Theatre.
These included the roles of Angelo Terrie in E. B. Dewing and Courtenay Savage's Don't Bother Mother (1925, Little Theater);[30] Freman in John Galsworthy's A Bit of Love (1925, 48th Street Theatre);[31] Baron Frederick in Rudolf Friml, Otto Harbach, and Oscar Hammerstein II's The Wild Rose (1926, Martin Beck Theatre),[32] Prince Hussein in Winthrop Cortelyou, Derick Wulff, and Max Simon's musical Kiss Me!
[39] In 1933 he returned to Broadway as Dr. Falke in an English language adaptation of Die Fledermaus entitled Champagne, Sec which began its run at the Morosco Theatre.
[54] In 1961 he portrayed the role of Lawyer Manson in Sheldon Harnick, Ira Wallach, and David Baker's Off-Broadway musical Smiling the Boy Fell Dead at the Cherry Lane Theatre.
[55] He starred in another Off-Broadway musical the following year; portraying Maloney in Bob Larimer's King of the Whole Damn World at the Jan Hus Playhouse.
On November 10, 1954 he portrayed the bartender in a television version of Panama Hattie broadcast live on the CBS anthology series The Best of Broadway which starred Ethel Merman in the title part.