That's what I'd recommend, and maybe I love black and white films now because when I was growing up in the late 80s I watched the Stooges.
I'm a TCM addict, my niche interest is 60s and early 70s stuff with subtitles. The 3 or 4 actors and the differing personas of Sam Spade in The Maltese Falcon and the Big Sleep is a fun study. See if the youngster concludes that Bogart doesn't rule. See if anyone can remotely untangle the plot of The Big Sleep while you are at it.
It was different when we were kids growing up in the late 50's and early 60's when TV was new. There were dedicated children's programming like Disney and Saturday morning cartoons. Still, all TV back then was in B&W. Since children's programming was more limited, we watched a lot of old movies that were now being recycled on TV. It was either that or nothing. This meant were were exposed to and were used to old B&W movies from the 30's and 40's. There were basically no or little special effects and everything depended on the story to engage audiences. It makes sense, when you think about these movies. Before TV, people went to movie theaters to watch anything visual. So there you were, all together in a darkened movie house, doing nothing but engaging in the movie for two hours. You tended to become immersed with the story. There were no other distractions. The same thing happened when these movies came to TV. You watched intently and becoming immersed in the storyline was a learned experience. I would think that you could not randomly pick out old classics and have any reasonable expectations of modern children having this same experience. I am not saying that it is not possible, I think that you have to ease them into it. The majority of adults today will not watch a B&W movie or foreign movies with subtitles.
I'm typically a big fan of movies older than the 1970s, but here's a couple that I thought were pretty good comedies: No Time for Sergeants (1958) with Andy Griffith The Long, Long Trailer (1953) with Lucille Ball and Desi Arnaz
I went for color, fair action, mystery elements. Black and white is too hard a sell. Vertigo - 1958 A Fistful Of Dollars - 1964 Bullitt - 1968
I kinda think that some of these choices are a bit... off. Like, I don't think kids are going to sit for an intense two hour B+W drama. I thought of another one. I took my daughter, who is now 13, to the Academy museum in LA six months ago. One of the exhibits was the backdrop of the Mount Rushmore scene from North by Northwest. When we got home I found the flick on line and we watched it together. She really liked that one. I think I might try Rear Window next.
For a black and white film, maybe Arsenic and Old Lace? That play still gets dug up now and again and performed by high schools, so kids might even be familiar with it. It's funny, sorta scary, and Cary Grant's performance is something else; it has a real post-modern winking-at-the-audience quality to it (and when you are talking about plays kids might know, how about the film version of Bye Bye Birdie?).
I think the real world connection had a lot to do with it. Also the fact that it took place in the Academy museum. Both of you were engaged with this movie from an industry perspective. I think that made all the difference. Not that it was a bad movie.
Key Largo Australian theatrical release poster Directed by John Huston Screenplay by Richard Brooks John Huston Based on Key Largo 1939 play by Maxwell Anderson Produced by Jerry Wald Starring Humphrey Bogart Edward G. Robinson Lauren Bacall Lionel Barrymore Claire Trevor Cinematography Karl Freund Edited by Rudi Fehr Music by Max Steiner Distributed by Warner Bros. Release date July 16, 1948 Running time 101 minutes Country United States Language English Budget $1.8 million[1] Box office $3.3 million (US/Canada rentals)[2] $4.4 million (worldwide)[1]
Angels with Dirty Faces Original theatrical release poster Directed by Michael Curtiz Written by John Wexley Warren Duff Based on Angels with Dirty Faces by Rowland Brown Produced by Samuel Bischoff Starring James Cagney Pat O'Brien The Dead End Kids Humphrey Bogart Ann Sheridan George Bancroft Cinematography Sol Polito Edited by Owen Marks Music by Max Steiner Distributed by Warner Bros. Release date November 26, 1938 Running time 97 minutes Country United States Language English Box office $1.7 million[1] Ending is a killer.
The Haunting Theatrical release poster Directed by Robert Wise Screenplay by Nelson Gidding Based on The Haunting of Hill House 1959 novel by Shirley Jackson Produced by Robert Wise[1] Starring Julie Harris Claire Bloom Richard Johnson Russ Tamblyn Cinematography Davis Boulton Edited by Ernest Walter Music by Humphrey Searle Production company Argyle Enterprises[1] Distributed by Metro-Goldwyn-Mayer Release date 18 September 1963 Running time 114 minutes[2] Country United Kingdom[3] Language English Budget $1.05 million Box office $1.02 million[4]
The Thing from Another World Theatrical release poster Directed by Christian Nyby Screenplay by Charles Lederer Uncredited: Howard Hawks Ben Hecht Based on based on "Who Goes There?" 1938 novella John W. Campbell Jr. Produced by Edward Lasker Howard Hawks Starring Margaret Sheridan Kenneth Tobey Robert Cornthwaite Douglas Spencer James Young Dewey Martin Robert Nichols Cinematography Russell Harlan, ASC Edited by Roland Gross Music by Dimitri Tiomkin Production company Winchester Pictures Corporation Distributed by RKO Radio Pictures Release date April 27, 1951 (US)[1] Running time 87 minutes Country United States Language English Box office $1.95 million (US rentals)[2]
My son loved the Marx Brothers when he was growing up. The anarchy and irreverence appealed to him then, as now.
For horror I would add/agree with: Cape Fear original The Thing From Another World (great story and ahead of it's time with very modern dialogue) Psycho Can't go wrong with Hitchcock so I'll add Spellbound which had aged very well. For some noir personal favourite: The Third Man Key Largo (nice simple compact plot) M Comedy - Kind Hearts and Coronets And lastly one of the best heist films, Rififi (french but much of it like a silent film)
Another movie you could show the kids is THE CHILDREN (1980). And THE BEYOND (1981-Italian) is fun, too. But only see the uncut version. "The Beyond" was mostly filmed in an around New Orleans with some SFX work done back in Italy.
Another vote for Young Frankenstein. Some 80’s comedies might have some appeal, especially some of the Gene Wilder and Richard Pryor movies.