Has he watched the Bourne movies? Those are a good distraction.

Great idea, OP! My DS sounds a bit like yours. Instead of movies, we usually binged TV shows together. It was nice because, since they were of shorter duration than movies, we could easily start/stop them. We also had a pact that we had to watch them together - no going off and watching by yourself. I focused on finding shows that he was unlikely to have seen before such as:

Warehouse 13
Grimm
Star Trek (all iterations)
Breaking Bad
Star Wars animated series
Last Airbender (original cartoon series - we later watched the movie and discussed)
X-files

On a side note, we used to do a regular family Classic Move Night (kids are in college so not so regular anymore). When I first made the pronouncement, the kids weren't that keen but I, of course, knew what amazing movies there were that had been made before they were born and selected GREAT ones. Later selections included those everyone needs to watch at least once - like Casablanca, The Good, The Bad and The Ugly, Singing in the Rain, etc. One of our favorites (if you don't mind the language) is the original Bad News Bears.

Moneyball?

The Americans?

Will Farrell movies like Talladega Nights or anchorman?

Overboard?

Hope he feels better soon!

Stepbrothers is a good suggestion.

Stand By Me is on hulu--my teens loved it

Resident Alien (show) on Netflix

Does he like sports? Maybe a sports documentary? The one about Lebron James is fun. Our kids also really liked The Dawn Wall and The Crash Reel is a story about resilience and flexibility with tons of crazy snowboarding clips thrown in.

Oceans 11

Donnie Darko and Stepbrothers are good suggestions. He likes sports, dry wit, spy stuff, he is pretty versatile. Probably want to avoid "underdog wins!" movies at this time due to the disappointment.

Thanks!

It depends on his personality.

My 15 year old loves all kinds of movies —action, mystery, drama, even Pixar.

He did recently see The Holdovers and said it was his favorite movie.

Does he like sports? What about Draft Day or Rudy? Or Miracle on Ice?
Has he seen A Quiet Place? The Edge of Tomorrow? Love and Monsters?
What about The Holdovers?
The Secret Life of Walter Mitty?
21 Jump Street (with Tatum and Hill)

If he hasn't seen some of the retro ones, I might try that too...
Back to the Future
Bill & Ted's Excellent Adventure
Donnie Darko
What About Bob

Stepbrothers

Had he seen both Top Gun movies?

If he likes dogs we just watched Megan Leary on Netflix. Based on a true story.

It’s a TV show but Monk is great.

What kinds of movies/shows does he like/has he watched? Netflix probably knows if you have that.

My teen is in a funk after a series of disappointments and socializing or rapidly fixing it isn't going to work this weekend. So my plan is to just have foods he likes and maybe a nice thing to watch together. And recommendations for an engaging movie for your average 15 yo boy? I am out of ideas and he'll say no to everything so I was planning to just sit near him and start the movie tonight.