Fortune 500 rank: 409
2007 loss: $1.62 billion
The disaster at Paul Allen's brainchild continues. The Microsoft co-founder once envisioned a cable company that would serve all kinds of media to its customers, but thanks to competition from satellite, other cable companies, telecoms and the Web, Charter can't meet the obligations of its huge debt load.
While operating revenues were up and Charter added nearly 700,000 net new subscribers, Charter still was forced to pay $1.9 billion to its creditors. Allen is rumored to be interested in taking the company private or selling it to a competitor. NEXT: Schering-Plough