Younger Hexbears, if the spirit of boomerdom visited your household, boomer is more a state of mind than a specific birth year, so feel free to share your stories too.
There are some obviously better-known movies like Wall Street, but I remember an obscure one called "Let It Ride" that was played on tape over and over and over again so many times that it was like the theme song of the household for a while. It was a Richard Dreyfuss film about a gambling addicted asshole who seeks to triumph over his gambling problems by... gambling. Until he gets vibes about winning and then wins at gambling. 
As a boomer bonus it portrays The Wife as a bad person because she's... upset at the protagonist's gambling addition. Oh yeah and she suspects he's eager to commit some adultery. How dare she... the way to show her is to have a much younger love interest that is totally into the protagonist because he starts to win at gambling! 
For anyone that has had gambling-addicted boomer parents, the kind that thought a fun outing for the kids was going to the racetrack, or to Vegas, you may have similar stories of poverty perpetuated because your 
also liked to "Let It Ride."
sean connery was the first instance that stands out to me growing up, where i realized that A-list actors can be really stupid. connery played some highly intelligent, moral and cultured characters (ex. Henry Jones Sr)... but in reality, he was a dumb ass with marketable voice and face. if you look at pictures of him when he was young, it's pretty obvious what he was bringing to the table.
i remember reading that story about how he was approached for the LOTR trilogy to play gandalf as literally the first choice. he turned down 30 million per flick and 15% of box office profits because he "didn't understand it." he ended up losing out on nearly half a BILLION dollars. he says he read the book and saw the movies, but still doesn't understand them. that is literally what he said. personally, i think LOTR is highly accessible material. you could show it to a child and they are not going to be confused by it. but 70 year old sean connery was fuckin' baffled.