Kodak

Kodak's 131-year dominance ended with a textbook case of innovator's dilemma. The company controlled 90% of US film sales, invented the digital camera in 1975, but refused to commercialize it to protect film profits. By 1997, its stock peaked at $94.25; by 2011, it traded below $1. Digital cameras and smartphones wiped out film, leading to a 2012 bankruptcy that eliminated 140,000 jobs—more than four times the 33,000 jobs lost at Toys "R" Us (#8). The company's failure to pivot cost shareholders $28 billion in lost market value.