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1990s / Jimmy Connors 1991 US Open
Considered washed up, 39-year-old tennis great Jimmy Connors surprised everone by reaching the semifinals of the U.S. Open in 1991 and made the cover of Sports Illustrated. Formerly disliked by tennis crowds for his bad behavior on court, Connors became a fan favorite late in his career. The fans went bonkers during Connors' unforeseen run at Flushing Meadow. His round-of-16 match versus Aaron Krickstein on Labor Day was an all-time classic. Said one bemused tour veteran, 'Jimmy has always been an ---hole. Now he's America's favorite ---hole.'