I think the films being referred to were more along the lines of "how to spend your millions", "what it's like to show off your superbowl ring", or commercials

I think the films being referred to were more along the lines of "how to spend your millions", "what it's like to show off your superbowl ring", or commercials where sports stars are asked "What are you going to do now?" and they respond "Go to Disney Land", as if these somehow indicated HOW to win. The films you're referring to are the proper ones to watch to, as you say, study the problem area and come up with winning strategies. It's not watching movies like Big to find out how to become an executive at a toy company or Gung Ho to determine how to run an auto manufacturing plant.