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 weren't into that sort of thing, but if you want a hilarious boomer esque B-Movie I highly recommend movies by James Glickenhaus. I think he might be one of my favourite directors of all time, and he only made about 4 actual movies.
They're pure right wing fantasy, the acting is terrible, the dialogue is hilarious, but then out of nowhere there's just the most ludicrous action scene you've ever seen with notes of fantastic cinematography. I find them so charming. They just come together so well.
In order I'd recommend:
The Soldier. It's like American James Bond. The most ridiculous of them all, so far that he almost seems self aware. USA works with the Israelis to stop some guy blowing up all the oil in the middle east with a nuke. At one point they ramp a car over the Berlin wall. As a bonus, the sound track is by Tangerine Dream, making the movie the first ever ambient action film.
Shakedown - in the UK it was called Blue Jean Cop. The movie opens with a young Sam Elliot in a trashy cinema, falling asleep to a scene on the movie screen from The Soldier, where The Soldier does a 360 Uzi noscope on a ski ramp. The action scenes in this one are an absolute masterclass, and the come out of nowhere. Glickenhaus even predicts 9/11 at one point.
The Exterminator - Porn tier acting in this one. A traumatised Vietnam vet goes around killing gang members and pedophiles with a flamethrower. The lead character is so uncharismatic that he's perfectly casted as the most unremarkable man ever. In one scene where he shoots up a party (that only 5 people are attending), some classic 80s pop song is playing the whole time. I don't remember which song, but it's absolutely hilarious.
McBain - Don't watch this one. Unless you're craving more Glickenhaus. This one stars a young Christopher Walken as some guy who stages a coup in some Latin American country... Except he seems to show up after every firefight is over and never really does anything? It's actually hilarious once you notice it, but it's just too long to be a proper Glickenhausian romp. It opens with bamboo cage fighting in Vietnam, and in the middle of it there's an awesome speedboat scene where quite simply, dudes are rocking. Otherwise, eh.
God, I've waited so long to put my love for those movies into words.
McBain ain't got nothing on Itchy & Scratchy.