information:filtering, information:classification, stylistic:tone
Breaking into theatre (1928–1932)

Hepburn left university determined to become an actress. The day after graduating, she traveled to Baltimore to meet Edwin H. Knopf, who ran a successful stock theatre company. Impressed by her eagerness, Knopf cast Hepburn in his current production, The Czarina. She received good reviews for her small role, and the Printed Word described her performance as "arresting". She was given a part in the following week's show, but her second performance was less well received. She was criticized for her shrill voice, so she left Baltimore to study with Frances Robinson-Duff, a renowned voice teacher in New York City.

Knopf decided to produce The Big Pond in New York, and appointed Hepburn the understudy to the leading lady. A week before opening, the lead was fired and replaced with Hepburn, which gave her a starring role only four weeks into her theatre career. On opening night, she turned up late, mixed her lines, tripped over her feet, and spoke too quickly to be understood. She was immediately fired, and the original leading lady rehired. Undeterred, Hepburn joined forces with the producer Arthur Hopkins and accepted the role of a schoolgirl in These Days. Her Broadway debut came on November 12, 1928, at the Cort Theatre, but reviews for the show were poor, and it closed after eight nights. Hopkins promptly hired Hepburn as the lead understudy in Philip Barry 's play Holiday. In early December, after only two weeks, she quit to marry Ludlow Ogden Smith, a college acquaintance. She planned to leave the theatre behind but began to miss the work and quickly resumed the understudy role in Holiday, which she held for six months.

In 1929, Hepburn turned down a role with the Theatre Guild to play the lead in Death Takes a Holiday. She felt the role was perfect, but again, she was fired. She went back to the Guild and took an understudy role for minimum pay in A Month in the Country. In the spring of 1930, Hepburn joined the Berkshire Playhouse theater company in Stockbridge, Massachusetts. She left halfway through the summer season and continued studying with a drama tutor. In early 1931, she was cast in the Broadway production of Art and Mrs. Bottle. She was released from the role after the playwright took a dislike to her, saying "She looks a fright, her manner is objectionable, and she has no talent", but Hepburn was re-hired when no other actress could be found. It went on to be a small success.

Hepburn appeared in a number of plays with a summer stock company in Ivoryton, Connecticut, and she proved to be a hit. During the summer of 1931, Philip Barry asked her to appear in his new play, The Animal Kingdom, alongside Leslie Howard. They began rehearsals in November, Hepburn feeling sure the role would make her a star, but Howard disliked the actress and again she was fired. When she asked Barry why she had been let go, he responded, "Well, to be brutally frank, you weren't very good." This unsettled the self-assured Hepburn, but she continued to look for work. She took a small role in an upcoming play, but as rehearsals began, she was asked to read for the lead in the Greek fable The Warrior's Husband.

The Warrior's Husband proved to be Hepburn's breakout performance. Biographer Charles Higham states that the role was ideal for the actress, requiring an aggressive energy and athleticism, and she enthusiastically involved herself with its production. The play opened March 11, 1932, at the Morosco Theatre on Broadway. Hepburn's first entrance called for her to leap down a narrow stairway with a stag over her shoulder, wearing a short silver tunic. The show ran for three months, and Hepburn received positive reviews. Richard Garland of the New York World-Telegram wrote, "It's been many a night since so glowing a performance has brightened the Broadway scene."