11. Eastman Kodak
Fortune 500 rank: 297
2009 revenue: $7.6 billion
2009 total shareholder return: -35.9%
The film and camera company's transition to digital hasn't really clicked. Faced with the unexpected pressure of the economic slowdown, sales dropped 19% last year.
Kodak made new forays into the commercial printing business, buts it still derives much of its revenue from traditional film.
In September the company issued debt and stock warrants to private equity firm KKR; the threat of dilution drove shares farther down.
NEXT: 12. KeyCorp
