"... a kid who is basically always in control and often naturally takes on leadership roles.... The fact that John Conner is a tough character who also has a strong sense of humanity and isn’t whiny or aggravating also resonated."
This is part of what made the third film such a disappointment. Instead of a more grown-up version of Eddie Furlong's John Connor we get a washed out loser with mommy issues breaking into a veterinary clinic to find something to shoot up. I recommend skipping to the fourth film and ending on a better note.
Not sure what else you've shown him or ruled out, but here are some recommendations:
Bugsy Malone (1976). This might qualify as a bit too silly, but it's a gangster movie with all the roles played by kids (and all the bullets played by whipped cream).
E.T. the Extra-Terrestrial (1982). Classic.
The Neverending Story (1984). Classic. The sequel's OK too.
The Karate Kid (1984/2010). Double classic, both the original and the Jaden Smith remake.
Return to Oz (1985). Darker cult classic sequel based on the second and third Oz books. This ain't no musical, but you might be a little disappointed that Tip doesn't make an appearance before he is transformed into Princess Ozma.
Ferris Bueller's Day Off (1986). If he's old enough to appreciate a Terminator movie, he's probably old enough to appreciate a classic ditch-day movie like this one.
Flight of the Navigator (1986). Underappreciated escapism. Boy on the run with an alien spaceship after having returned to Earth the same age he was years after he went missing.
Stand by Me (1986). Please tell me you've already screened this one.
Hope and Glory & Empire of the Sun (1987). Perhaps two of the best WW2 coming-of-age films.
Honey, I Shrunk the Kids (1989). After accidentally getting shrunken to a millimeter in size, four kids try to get home while dodging the dangers of their own backyard. Sort of a kid-friendly survival adventure.
The Witches (1990). Two boys get turned into mice while visiting a hotel and stumbling upon a witch's convention.
Hook (1991). Maybe he'll take a liking to Rufio?
The Sandlot (1993). Classic baseball kid film. With that in mind, he might also like The Bad News Bears (the original, not the sub-par remake).
Dazed and Confused (1993). If he likes Ferris Bueller, he might be ready for this more adult-oriented coming-of-age film.
Jumanji (1995). Boy gets sucked into the Jumanji-verse and gets spit back out years later all grown up... along with a bunch of other jungle critters.
Wild America (1997). Loosely based on a true story, three underage brothers head out into the wilderness to film their own nature documentary.
The Mummy Returns (2001). Strong Indiana Jones vibe with this one along with a cute kid at the center of the action. Part 1 is also a solid action/adventure film, but unnecessary to understand the second movie.
The Road to Perdition (2002). Father and son on the run from the Irish mob.
Holes (2003). Juvenile delinquents versus some shady authority figures. An all-around crowd-pleaser.
Master and Commander: The Far Side of the World (2003). A boy officer has a supporting role, loses an arm early on in the film, and later gets to take command of the ship. Might be a bit too historical (Seven Years War and such).
A Series of Unfotunate Events (2004). Key takeaway: Every adult in this film who is supposed to be looking after the kids' best interests is totally incompetent. It's the kind of subtext one might appreciate if they're cynical about the system.
Duma (2005). South African boy adopts a cheetah cub. When the animal becomes too big to keep, they run off into the wild together to reintroduce it into its natural habitat. Really special movie.
Son of Rambow (2007). Two boys decide to film a Rambo movie together. Also special.
Superbad (2007). More from Ferris Bueller territory.
True Grit (2010). Remake of the old John Wayne film (based on the novel), a young Hailee Steinfeld heads out into the wild west to track down her father's killer with the help of an old coot of a ranger.
Sing Street (2016). A 15-year-old boy transfers to a rough school and decides to start a band to impress a girl he likes. Then the project and the friends he makes along the way start to mean something more to him beyond merely being a means to an end. One of my favorite scenes happens after the boy has hit a big rough patch with the girl and decides to redirect his energy by visiting his band-mate (the Lennon to his McCartney) to write a song together. Just the way his band-mate smiles at the request is just so amazingly bro-tastic that it will make you believe in the power of a good friend in tough times (but totally platonic! I swear!).
Kubo and the Two Strings (2016). Quality stop-motion fantasy adventure film that's actually a lot deeper than it might seem. Kubo's grandfather, the moon god, has taken one of Kubo's eyes and wants to take the other one too in exchange for the promise of immortality (because faith is blind?). Starting with the opening dialogue the concepts of memory loss and death are thematically linked as well as remembering the dead to keep them alive in your heart. A hint about the meaning of the title: Kubo's zither uses three strings, not two.
Concrete Kids (2018). Super-realistic depiction of two young skater boys who go out onto the streets on their own to get to a basketball stadium downtown.
Mowgli: Legend of the Jungle (2018). Disney's sucks ass. This one is far superior. Mowgli must decide where he fits in only to realize that he's his own person who can chart his own independent path.
If I had to narrow this list down, I'd hang onto Duma, Sing Street, Kubo, and Mowgli. Whether those personal faves match up with your boy's tastes is another thing.
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