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The first Hollywood connection surfaced by my quick googling is the Semel arc, 2001-2007:

http://www.cnet.com/news/yahoos-ceo-reaches-out-to-hollywood...

http://www.cnet.com/news/google-vs-yahoo-clash-of-cultures-1...

http://www.wired.com/2007/02/yahoo-3/

http://metue.com/06-18-2007/yahoo-ceo/

The Wired article looks particularly painful. If memory serves, Yahoo first declined to buy proto-Google for one million. Then again in 2002 for 5 billion.




Pretty much everyone with a million dollars laying around declined to spend it on acquiring Google back then, it's not like Yahoo was the only company they approached.




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