17 of 20
17. Harrah's Entertainment
Harrah's Entertainment
Fortune 500 rank: 263
Loss: $5.2 billion

The two private equity firms that bought the casino operator in 2007 for $17 billion drew a bad card: a recession that pushed revenues down 8.4% last year and deflated the once-ballooning valuations for gambling companies. Apollo and TPG wrote down the value of their investment by $5.5 billion, while Standard & Poor's dumped Harrah's debt into the lower end of the junk range and some analysts started predicting bankruptcy.

But assuming the private equity shops can stave off their creditors, they still have big plans. They bought a Macau resort in 2007 and opened up two London Club-brand casinos in the U.K. last year. Projects in the U.S., like the expansion of Caesar's Palace in Las Vegas and Margaritaville in Biloxi, Miss., have slowed - but not yet been canceled.

NEXT: Macy's
Last updated April 21 2009: 3:34 PM ET
Top 50 Exxon Mobil pushes Wal-Mart aside to retake the No. 1 slot this year. Which other companies made the top 50 this year? More
They're hiring! As many big companies are announcing mass layoffs, these Fortune 100 employers have at least 150 openings each. More
Best big companies to work for See the 31 companies that made both the Fortune 1000 and Best Companies to Work For lists this year. More