I can’t really figure out how to summarize this into an intelligent title, so let me try an example.
Obviously Danny Glover and Mel Gibson became synonymous as the Lethal Weapon guys over the course of (a dozen?) years.
Subsequent to that, there was a comedy-western movie that Mel Gibson starred in, and in it, Danny Glover had a brief cameo where he and Gibson crossed paths, and gave looks to each other (in character) as if to say “wait… is that… you? aw, nevermind, couldn’t be”.
For some reason, that always struck me as an extremely clever movie-moment. Any other examples of this sort of thing? I’ve seen the previews for Tim Allen’s latest sitcom “Home Improvement II” or whatever it’s called, and I thought it would be kind of cool if Patricia Richardson (the original “wife”) made some sort of a cameo as someone he crosses paths with.
Hence the question - trying to think of other examples of this that actually happened in film/TV. (I thought in one of the ‘Modern Family’ threads, someone mentioned where O’Neill/Sagal - i.e. Al/Peg Bundy - cameo’d together in something much later on, but I can’t find the thread).
Coming to America has Ralph Bellamy and Don Ameche – who co-starred with Eddie Murphy before in Trading Places running into him there.
The Mary Tyler Moore Hour was part sitcom and part variety show with Mary Tyler Moore as Mary McKinnon, who had a Carol Burnett-like TV show. Once they were having Dick Van Dyke as their guest; her writers pointed out how Mary McKinnon looked like the actress who played Laura. There were a couple of “Rob and Laura” skits, but the payoff at the end was when Mary McKinnon told Van Dyke that she had been up for a role on his show, but that Rose Marie got the part instead.
Bob Hope, Bing Crosby, and Dorothy Lamour had a thing going on and would regularly cameo in each other’s films, after having first been united in the Road movies.
I don’t know if this is what you’re looking for, but Scott Bakula and Dean Stockwell, who were co-stars on “Quantum Leap,” were reunited in an episode of “Enterprise.”
Apocalypse Now? Really? I thought that they both said Wall Street. They were both in it, and played father and son, and son was an out of control drug abuser that the father was trying to reign in.
And both Martin and Emilio appeared on 2.5 Men.
Before Christopher Lloyd and Danny DeVito were on Taxi, they were in Cuckoo’s Nest together.
And while this doesn’t really count towards the OP, there was a moment on Third Rock where John Lithgow and William Shatner talked about a disturbing plane ride. One of the best moments on that show.
Mary Tyler Moore played Jackie’s bitchy TV Boss on That 70’s Show. At the end of one of the episodes, she bitched about how all the news was about Minneapolis, yet the show is set in Chicago. She asked to see the news writer. In walked Garin MacLeod.
Spin City had Michael J. Fox seeing his therapist, “who is like a father to me.” The therapists opens the door.Cameo of Michael Gross.
I remember watching an episode of “The Love Boat” sometime after the run of The Brady Bunch in which both Robert Reed and Florence Henderson guest-starred. Their respective stories didn’t overlap, but there was one scene where they ran into each other in a buffet lane, and exchanged curious, “haven’t I seen you somehwere before” looks.
DECADES after the last “Road” movie, Bob Hope starred in a lame Western comedy called Cancel My Reservation. In one scene, Hope, who’s a murder suspect, is dreaming that he’s about to be hanged by a posse. Hope cries out, “Help me, help me.” And across the street, we see Bing Crosby laughing, “Help you? Who do you think bought the rope?”
Prior to Star Trek, both Shatner and Nimoy were guest stars on an episode of The Man from U.N.C.L.E., but they were on opposite sides. This is the opposite of the OP, but I saw the UNCLE episode long after having seen all the Star Trek episodes.
They also had his mentor show up, as played by Christopher Lloyd, playing can-you-top-this with increasingly obvious references: as they’d worked together in the past, they can now go back to working for a better future…