NEW YORK—Wall Street climbed again Friday, wrapping up its biggest five-day rally in more than 75 years, even as investors digested signs of a bleak holiday season for retailers and fears that a flurry of reports next week will show more economic distress.

On the short trading day, investors snapped up the battered shares of blue-chip stalwarts Citigroup Inc., General Motors Corp. and Ford Motor Co., fueling a rally that has surprised many market experts whipsawed by wild swings during the past three months.

The market got big boosts over the past week from President-el...

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