Katharine Hepburn won the Best Actress Oscar four times - the most of any woman in history. She won the award in 1934 for her performance in "Morning Glory." The same year, she divorced her husband, Philadelphia businessman Ludlow Ogden Smith. She won the award once again in 1968 and 1969 for "Guess Who's Coming to Dinner" and "The Lion in Winter," respectively. Those wins came on the heels of her break-up with boyfriend Spencer Tracy (pictured above). The win in 1982 for "On Golden Pond" was just for good measure.
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