NEW YORK - Wall Street resumed its sell-off Wednesday after oil hit a new record and a bearish analyst report renewed concerns that General Motors could run out of cash.

The stock market's pullback, which accelerated in the final hours of the week's last full trading day, left the Dow Jones industrial average officially in bear market territory, with the blue chips having fallen more than 20 percent from their October highs.

Oil surged to new records above $144 a barrel as the government reported a bigger-than-expected drop in U.S. supplies and as investors worried about tensions in the Middle East.

Worries that GM could go so far as to declare bankruptcy only added to investors' unease. The stock fell $1.77, or 15 percent, to $9.98 -- the first close below $10 since September 1954 when Dwight Eisenhower was president. Investors shrugged off better-than-expected sales figures from June and fretted about the company's cash needs.

The Dow fell 166.75, or 1.46 percent, to 11,215.51, the lowest close since August 2006. It now stands 20.82 percent below its Oct. 9, 2007, record of 14,164.53.

Broader stock indicators also posted big losses after showing gains for much of the morning. The Standard & Poor's 500 index fell 23.39, or 1.82 percent, to 1,261.52, while the technology-laden Nasdaq composite index fell 53.51, or 2.32 percent, to 2,251.46.

The S&P is just shy of the 20 percent pullback that signals a bear market. While the Nasdaq is also in bear market territory, it hit that mark in March, moved higher and has now returned to a bear level.

Wall Street is worried that rising energy prices are causing consumers to pare their spending in other areas.

Businesses are also struggling with elevated energy costs, and demand is weakening for autos, heavy machinery and steel. The Commerce Department said Wednesday that factory orders rose by 0.6 percent in May. The result was in line with Wall Street expectations but was much smaller than the gain of 1.3 percent for April.

"I don't think this is an investors' market right now," he said. "I think there is a lot of money on the sidelines, and once you get some kind of good catalyst -- anything to make the market look better -- they'll come rushing into the market."

Overseas, Japan's Nikkei stock average fell 1.31 percent. Britain's FTSE 100 fell 0.98 percent, Germany's DAX index slipped 0.17 percent, and France's CAC-40 fell 1.03 percent.