The month of May marks the birth anniversaries of multiple Old Hollywood film icons, including Audrey Hepburn, Henry Fonda, and James Stewart. But no other screen legend born in May has been more known for her fierce independence, headstrong persona, and overtly feminist mindset than Katharine Hepburn.

Born on May 12, 1907, Katharine Hepburn rose to prominence in A Bill of Divorcement in 1932, starring opposite veteran screen star John Barrymore (yes, Drew Barrymore’s grandfather). A year later, she quickly rose to the top of Hollywood’s echelon of stars, winning an Academy Award for Best Actress in 1934 for her performance in her third film, Morning Glory.

Suddenly at the top and under contract with one of Hollywood’s five film studios, RKO Radio Pictures then tried to find out what its blossoming star’s film persona should be but failed.

For a woman exuding modernity, they kept placing her in period films, which resulted in a string of flops in the 1930s. In fact, the box office receipts of Hepburn’s films were so terrible that she was listed by the Independent Theater Owners Association as “Box Office Poison” along with other stars.

This did not deter Hepburn, as she says in her memoir, Me: Stories of My Life, decades later: “I decided to go back East and do a play or something else.” The play that she would go on to do, would end up being her most iconic role of all time, Philip Barry’s The Philadelphia Story. It would open in 1939 at the Shubert Theatre on Broadway and would become her comeback vehicle to Hollywood, and it was off to the races from there.

She won a total of four Academy Awards for her performances in the films Morning Glory (1933), Guess Who’s Coming to Dinner (1967), The Lion in Winter (1968) and On Golden Pond (1981) – the most any person has ever received.

Hepburn’s illustrious career lasted until 1994, where she slowly bowed out of the film industry at the age of 87. In 1999, the American Film Institute placed Hepburn at the top of the list of the 50 Greatest American Screen Legends.

To celebrate this iconic film star’s enduring career, here are five of her best film roles to get you started on your classic film journey.

The Philadelphia Story (1940)

A great place to begin your watch list is this classic tale of remarriage. A romantic comedy starring screen icons Hepburn, Cary Grant and James Stewart caught in some sort of romantic rectangle is a film not to miss.

Hepburn plays Tracy Lord, a New England socialite who has great expectations of herself and the people around her, to the point that she appears to find human imperfection unforgivable. By the end of the film, she has to learn how to be more forgiving to herself and others.

Film critics of the era often said Hepburn plays no other character but herself, and this film sure is a mirror to how audiences perceived her in 1940.

Woman of the Year (1942)

This classic workplace romance pairs Hepburn with her eventual longtime partner, Spencer Tracy. Hepburn shines as Tess Harding, a renowned international journalist whose job demands she be on call 24/7, which doesn’t bode well for her marriage.

The film reveals the marital struggle of having a woman as the breadwinner in 1940s America, and how the pair figured that out. This film also spawned a Broadway musical in the 1980s starring another screen legend, Lauren Bacall, in Hepburn’s role.

Bringing Up Baby (1938)

This classic screwball comedy stars Hepburn and Grant, chronicling their insane antics. Hepburn beams as the scatterbrained, free-spirited Susan Vance navigates and instigates a mad-capped adventure which involves a tamed leopard from Brazil, an actual wild leopard, and a yapping dog. The film bombed at the box-office upon its initial release but is now considered by some as the best screwball comedy of all time.

The African Queen (1951)

The film pairs Hepburn and one of AFI’s Greatest Actors of All Time, Humphrey Bogart, in an adventure classic filmed on location in Uganda and Congo – one of the first film productions to shoot on location, and not in a studio.

The film is set at the outset of World War I in Africa where Hepburn plays a prudish British missionary named Rose Sayer who learns to adapt as she travels through rapids and African wildlife.

Holiday (1938)

In Holiday, Hepburn steals the show as the free-spirited thinker Linda Seton, who yearns to break free from her conservative elite family’s shackles. Partnered once again with Cary Grant, she takes her destiny into her own hands, charting the course for her own future. – Rappler.com