Which retail failure led to one of the most expensive product placement blunders in film history when the featured brand went bankrupt before the movie was released?

Product placement in film and television has evolved from subtle background appearances to sophisticated marketing strategies worth billions. These brand integrations can make or break a film's budget and have sometimes created iconic cultural moments. How well do you know the business strategies behind what products appear on screen and how studios have leveraged these relationships?

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Circuit City's prominent placement in 'Transformers: Revenge of the Fallen' (2009)
Borders Bookstores' integration in 'The Day After Tomorrow' (2004)
Schlitz Beer's campaign in 'Jaws' (1975)
Pan Am Airways' extensive branding in 'Quantum of Solace' (2008)