Excluding the genre of alternative history, actors and actresses playing famous people, and famous people doing cameos in movies or TV shows (like Stephen Hawking’s appearances on The Big Bang Theory).
What I’m thinking of is more like:
I just watched *Misery *with James Caan and Kathy Bates, based on the Stephen King novel. It’s pretty good. I noticed that Bates’s character had a little shrine set up to Paul Sheldon, the famous author played by Caan. It included a framed picture of Sheldon in a tux, meeting Queen Elizabeth II (presumably taken when the Queen attended some premiere of a Caan movie IRL).
Harry Bailey in It’s a Wonderful Life was awarded the Congressional Medal of Honor by President Harry Truman, as shown on the front page of the Bedford Falls newspaper.
Jack Aubrey in the Napoleonic naval adventures of Patrick O’Brian is proud to have once shared a meal with Lord Nelson (who at the time uttered that deathless phrase, “May I trouble you for the salt, sir?”).
In “The Adventure of the Bruce-Partington Plans,” Sherlock Holmes was given an emerald tie pin by “a certain gracious lady,” strongly implied to be Queen Victoria, for services rendered to the Royal Family.
Johnny Smith in Stephen King’s novel The Dead Zone meets Jimmy Carter, at the time a near-unknown candidate campaigning in New Hampshire before the 1976 Democratic primary.
Flashman rubs shoulders with lots of famous people, obviously. And there are all the VIPs shown, thanks to CGI and manipulation of historical footage, in Zelig and Forrest Gump.
Doctor Who-The Doctor has met scores of historical people but my favorite episode of that type is “Vincent and the Doctor”, in which Matt Smith’s Doctor has an encounter with Vincent Van Gogh.
Mr. O’Malley, Barnaby’s fairy Godfather, would often ramble on about meeting famous people, usually resulting in disaster. For example, he’d talk about meeting Captain Smith of the Titanic and telling him they should go faster.
Wait a minute, famous people played by an actor doesn’t count?? Just some oblique reference in like a newspaper (invariably photoshopped) or a character name dropping that he met soandso? Is that right?
The Young Indiana Jones Chronicles was one giant exercise in name-dropping. Take just about any important person in the early or middle 20th Century. Indy either worked for them, worked with them, went to school with them, lived next door to them, fought with or against them in World War I, dated their sister, (or, if a female, he had a passionate but doomed romance with them).
Unusual example; the recent independent movie The House of Tomorrow, based on a 2010 novel, was about an elderly woman and her grandson who live in a geodesic dome house, built by Buckminster Fuller. They also give tours of the house and talk about the architect. In one scene in the movie, the grandmother, played by Ellen Burstyn, is shown on videotape talking to Buckminster Fuller and on a sailboat with him. The footage is real, because Ellen Burstyn really knew the architect and spent time with him. So the fictional character is shown with the actual famous person, because the actress spent time with the actual famous person.
Horatio Hornblower and Richard Sharp encounter a lot of Napoleonic-era celebrities in their novels.
Sir Wilfred of Ivanhoe meets Robin Hood and King Richard. (I am giving Robin Hood the benefit of the doubt, and assuming that he was based on real outlaws.)
In War and Peace, characters interact with Napoleon, Tsar Alexander, Dowager Empress Maria, and Prince Kutuzov.
Another example, in the Tom Clancy novel Patriot Games, Jack Ryan saves the lives of Prince Charles and Princess Diana (in the book, they’re still happily married). Later in the book the prince and princess visit the Ryans’ home in America. (The movie version changed the character to a fictional royal.)
There are scads of books, TV shows, and movies in which fictional characters interact with real people. I think it’d be hopeless to try to list them all.
One interesting case is James Hogan’s science fiction novel the Proteus Operation. It’s a time travel novel. To the best of my knowledge, Hogan is the only person to write such a novel where he got permission from the real characters (at least those still alive) to use them in his story, such as Isaac Asimov.
It’s sort of the opposite of W.P. Kinsella’s Shoeless Joe, where he included the real-life author J.D. Salinger as a character without his permission*’ Salinger was reportedly furious, and threatened legal action if they used his real name in adaptations. So when they turned the book into the movie Field of Dreams, they changed his character to the wholly made-up Terence Mann (played by james Earl Jones).
*Kinsella sort of thought he was repaying Salinger for using a character named Kinsella in one of his stories. He said that he wrote Salinger’s character (he never met the man) as a real good guy “so he wouldn’t get sued.”
D’Artagnan and the Three Musketeers work for King Louis XIII, and in the sequels, King Louis XIV. In one of the sequels, Dumas implies that a Moliere based a character in The Misanthrope on Porthos.
In just about any novel by Alexandre Dumas, Rafael Sabatini, or Baroness Orczy, the characters will encounter a number of historical figures.
Robert Downey Jr.'s character in Restoration works for King Charles II.
I recall a movie review of a historical biography, and the reviewer said something along the lines of how it reminded him in an awkward way of a clutzy old-fashioned movie biography made in the past. Where a group would be discussing something and one of them would say, ‘oh, wait, here comes Beethoven now, let’s ask him what he thinks’. I thought that was kind of hilarious.
IMO Rowan Atkinson’s Mr. Bean could work, as in the original live version (15 episodes over 5 years - don’t know about the movies or the specials) he met Queen Elizabeth in a receiving line at a theatre (and knocked her over when bowing), and in the following cartoon series (oh yes, there is a pretty decent cartoon series, 100+ episodes and more planned to be made) he meets or interacts with Queen Elizabeth at least 4 times, probably more, including washing her limo and winning a garden show prize from her. Mr. Bean probably met other real world people as well, I just don’t recall them.
Speaking of fictional Rowan Atkinson characters who met ‘real world’ people, two words - ‘Black Adder’. Enough said (although I don’t recall if he met any real world characters in Black Adder goes forth - the Red Baron maybe?)
The gang on Murdoch Mysteries has met Nikola Tesla, Arthur Conan Doyle, Buffalo Bill Cody and Annie Oakley, Harry Houdini, H.G. Wells, Jack London, Henry Ford, Alexander Graham Bell,
Winston Churchill and Thomas Edison.
In my favorite book, If I Never Get Back, the protagonist meets Mark Twain, and travels with the entire 1869 Cincinnati Red Stockings team. Not long after I read the book for the first time my family and I went to the Baseball HOF and it was a real treat to see all the guys from the book in the Hall!!
There are a few Bret Easton Ellis novels in which a fictional character meets an actual person, but Glamorama has to have the most. I think Skeet Ulrich has a full chapter. It’s been about 15 years since I read it though, so I can’t remember the specifics. There may have even been a scene where Patrick Bateman is at the same party as Christian Bale.