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."
My Parents once made me watch The Game. It's one of those movies where everything is supposed to be super mysterious and relies on the spectacular twist ending while also including a ton of expensive but boring action sequences. It's about a billionaire who has some personal issues and his brother stages a huge conspiracy (that's the revealing twist at the end) to make him value life again and rediscover his good side. The whole thing is incredible stupid. Especially the ending, where he shoots someone with a gun that he thought was fake and therefore tries to kill himself by jumping off the rooftop only to be caught by a giant air pillow that was placed there by his brother. When he emerges from the pillow, everyone involved in the conspiracy, including the guy he thought he shot, is there to wish him a happy birthday. He now is a better man and the actress who fake falls in love with him during the conspiracy is now really in love with him.