What books and movies feature two people imprisoned or otherwise stuck together?
The only one that springs to mind for me right now
is the movie “The Kiss of the Spiderwoman” which I’ve seen, based on the novel by Manuel Puig which I have not read.
Forbidden Planet is about the rescue of two people marooned together.
The Defiant Ones involves two people handcuffed together, as does part of The Thirty-Nine Steps.
Fled – Yet another “Defiant Ones”-style handcuffed together movie.
Wedlock / Deadlock – Corny sci-fi action thriller starring Rutger Hauer. He’s stuck with another prison as they’re both wearing exploding collars that detonate if they get too far from each other. There was also a sequel / rehash.
The first thing I thought of was the SF story by Barry Longyear, although the two “people” are of different species.
Just don’t mention the movie around Barry. 
Swept Away (both the 1975 original and its 2002 remake)
Six Days Seven Nights (1998)
Heaven Knows, Mr. Allison (1957) and the similar Father Goose (1964) except that had a bunch of kids in it as well
*Side Show*, the ultimate “stuck together” story.
Hitchcock’s The 39 Steps features two people handcuffed to each other for the better part of the movie.
There’s Nicolas Roeg’s Castaway (not to be confused with Tom Hank’s Cast Away), with Oliver Reed and Amanda Donohoe, but they choose to maroon themselves on a desert island. It’s based on a true story, a book by Lucy Irvine. Unfortunately, it’s not on DVD. The soundtrack is WAY kickass, but it’s out of print.
Here’s the trailer.
Wikipedia link for movie.
Lucy Irvine’s website.
Of course, Enemy Mine is based on an earlier movie Hell In The Pacific
Robinson Crusoe and Friday, of course.
The detective and the cartoon bunny spend a scene handcuffed together (unnecessarily, as the bunny can escape any time he wants to) in Who Framed Roger Rabbit.
There was a Star Trek: The Next Generation episode, “Attached,” in which Capt. Picard and Dr. Crusher were joined telepathically by brain implants, and became ill if separated: Attached (episode) | Memory Alpha | Fandom
Robinson Crusoe on Mars.
Does Stephen King’s Misery count?
**All of Me **[Steve Martin’s character suffers Lily Tomlin’s spirit being trapped in his body]
D.O.A. [both versions, I think – I don’t remember if the doomed man spends much of the movie on the run and handcuffed to a woman in the original version, as Dennis Quaid did with Meg Ryan in the remake.]
**The War of the Roses ** [divorcing couple agree to split their house into two hostile territories. Not a prison in the usual sense, but they’re both trapped together.]
It Happened One Night
Sorta. Annie was trapped by her madness. How about Gerald’s Game? There’s nothing like being shackled to a corpse!
Shacled to the bed. Let’s not make King sicker than he already is.
Slightly off topic, the bail bondsman and the fugitive in Midnight Run, and the FBI agent and the fugitive in Flashback, are handcuffed to each other for big chunks of their respective movies, IIRC.