Every weekend I visit my elderly parents for dinner and a movie. My Mom likes almost anything, but my Dad is very hard to please. The only thing he usually likes to watch is sports and news (and I don’t need to tell you what news he watches).
Movies I know he likes. We just watched Song Sung Blue with Hugh Jackman. We all loved that one. He loves movies from the 50s and 60s. His favorite movie of all time is The Sound of Music. At Christmas his favorite film is White Christmas with Bing Crosby. So obviously he likes musicals but they have to be on the older side. He didn’t like Hamilton at all and I’m not sure about Chicago but I’ll probably recommend that one night.
He generally doesn’t like car chases, gun fights, or spy movies. He was a banker so he kind of liked Margin Call. He also kind of liked Wolf of Wall Street but it was a little too crass for him. I don’t think he cares about the nudity, it’s the cussing that gets to him. I think he doesn’t like car chases and gun fights because he doesn’t like modern action sequences. I do think he likes some older Steve McQueen movies though like Bullitt (which I haven’t seen and will suggest because I do want to see it).
As I mentioned, he’s a huge sports fan so he knows all the back stories. I thought he’d love Money Ball, but he knew that the movie was taking a lot of liberties on the true story. Even though he doesn’t like car chases he really loved Ford vs. Ferrari but was only so so on Rush. I don’t think he was a big fan of F1 but I think that was because the story was a bit weak.
He absolutely hates Sci Fi so nothing in that category.
If he liked Moneyball and he’s a banker, see if he likes The Big Short. It’s another adaptation of a Michael Lewis book. Could also try The Sting.
As for musicals, I don’t think you can go wrong with The Music Man, with Robert Preston (and a young Ron Howard).
I like submarine and aviation movies. Here’s my list if he cares to try:
12 O’Clock High (from the 1940s with Gregory Peck) The Great Waldo Pepper (Robert Redford) Hunt for Red October The Enemy Below The Caine Mutiny (Humphrey Bogart)
There are a bunch of sports bio pics from the 50s and 60s, all pretty clean. Jim Thorpe, Lou Gehrig, “Crazy Legs” Hirsch films have tragic elements, but are good as I recall. And Brian’s Song from the 60s - the one film men of that era are “allowed” to cry over. The Babe Ruth biopic is also good as I recall, and pretty sanitized.
The Francis the Talking Mule comedies may be up your Dad’s alley. I don’t know how they age.
Would y’all enjoy revisiting some of the classics from the forties and fifties? Casablanca and other Bogart vehicles, North by Northwest and other Hitchcock classics, The Third Man and other noirs, Bringing up Baby and other screwball comedies? These sound like they might be right in his wheelhouse, and also might bring up some nostalgia for him.
If your father’s “favorite movie of all time” is The Sound of Music, I would take it for granted there is nothing I could recommend that would please him. That said, I will mention Inside Straight, an obscure and underrated 1951 film about an unscrupulous man in late 19th century San Francisco who repeatedly builds and loses a financial empire, ultimately leading to a climactic, very high stakes poker game. It’s an older film, no cussin’ or car chasin’, that deals with banking issues. - https://www.imdb.com/title/tt0043676/?ref\_=hm_rvi_i_2
House of Rothschild (1934) and House of Strangers (1949) also deal with banking issues.
The Match King (1932) is a fictionalized version of the life of Ivar Kreuger - Wikipedia and his attempt to gain a worldwide match monopoly through banking misbehavior.
If your dad is a sports fan you might do like I sometimes do and look up and old game on YouTube. You can occasionally find full length broadcasts. He might get a kick out of watching Jackie Robinson bat while Yogi Berra catches (retro NFL games from the 70s are also fun)