NOTE: An actor "playing the same character over and over" is often a comedian playing themselves, or simply someone with a lack of range. Either way, think long and hard about whether they truly qualify for this trope before adding them.
Despite the use of many other characters from the comics, the Batman movies also have Expys for some characters:
Tim Burton didn't want to use Harvey Bullock in the 1989 Batman movie, so he created the overweight, gruff, corrupt Lt. Eckhardt in the Batman movie.
Jack Napier is not only The Joker, but an Expy of Joe Chill, the mugger who killed Thomas and Martha Wayne.
In The Dark Knight, you have Officers Stephens and Ramirez, who are essentially Expys for Harvey Bullock and Renee Montoya, with the exception being that Ramirez is actually a traitor. Stevens on the other hand is Bullock right down to the toothpick chewing but his name was probably changed so the film wouldn't have two characters named Harvey.
It's rumored that Ramirez was supposed to be Montoya, but was changed to an original character because of the revelation that she was actually a crooked cop.
With Terry Gilliam directing and Michael Palin in a supporting role, Brazil featured expies of the rest of Monty Python, all seen here:
Sam (Jonathan Pryce), the naive, bemused protagonist => Graham Chapman
Sgt. Stone seems to be a replacement for professional wrestler Sgt. Slaughter. Oddly, he's not the first Expy of him, with Beachhead having also filled the role. He also aligns with multiple "Lt. Stone" characters in Joe cartoons and comics.
In Gremlins 2: The New Batch, one Mogwai looks and acts very similarly to Stripe from Gremlins. The music sting, the way the camera zooms in and Gizmo's reaction all make it abuldantly clear to everyone including Gizmo that, for all intents and purposes, Stripe has been reborn. (Technically, both characters are brothers, as they both popped out of Gizmo's back after he got wet, and the New Stripe has black and white fur rather than brown and white, and after he becomes a gremlin, he has a reptilian frill rather than a Mohawk. But still undeniably an expy of Stripe.)
The villains in each of the direct sequels to Highlander — Katana in Highlander II: The Quickening, and Kane in Highlander III: The Sorcerer — were pale imitations of the Kurgan, the memorable villain from the original. Kane even had the same deep, rough Dr. Claw voice as the Kurgan. Likewise, the villain from the TV series' pilot "The Gathering", Slan Quince, was also a Kurgan expy.
Being an Affectionate Parody to superhero movies in general (and a VERY good one at that, seeing that it won two Oscar Awards and all), it shouldn't be a surprise that The Incredibles thrusts a whole lot of superhero expies in your face from start to finish.
The family is very nearly the Fantastic Four. Even their costumes and name (Fantastic/Incredible) are similar:
Jack-Jack, who is shown to have highly variable superpowers at the end of the movie, is based on Franklin Richards, the young son of Mr. Fantastic and the Invisible Woman who has ill-defined but incredibly vast powers.
Syndrome, is a somewhat more rotund Doctor Doom, a villain whose primary superpowers are simply being so good at super-technology that his super-suit is more powerful than the family combined.
Frozone is basically Iceman from the X-Men comics as played by Samuel L. Jackson. They even have the same way of getting from place to place: creating ramps of ice to skate everywhere.
In a more extreme example, Gazerbeam and The Underminer basically are Cyclops and the Mole Man, an enemy of the Fantastic Four, in all but name. The DVD special features on the minor heroes in the movie even parodies Cyclops's infamously bland personality by having Gazerbeam be an incredibly dull person.
Edna is based on a real-life costume designer for Paramount, Edith Head. Compare Edna◊ and Edith◊. Many say she was based on Linda Hunt's character Regina Krumm in Altman's 1994 film Pret-a-Porter. There is a serious resemblance, down to her size, her hairstyle, her black dress and her circular glasses!
If a place can be an expy, than the middle school that Violet attends is one for Corvallis High School in Corvallis, Oregon, where Brad Bird went to high school. This is down to them having the same mascot (the Spartans). However, since the high school building was torn down in 2005 and rebuilt, it's a little hard to see it now.
It even extends to the comic, which has featured among the expanded rogues gallery a Gorilla Grodd expy and aliens resembling the tentacles. And the Humongous Mecha piloted by the Underminer in an effort to frame the Incredibles resembles The Iron Giant with a red paint job.
Possibly more of a Shout-Out, given Brad Bird's involvement in both.
William Gibson's recurring character Molly Millions was present in the original short story "Johnny Mnemonic," but was replaced with a similar Action Girl named Jane in the film. The rumour is that this change was made because of some arguments about the film rights for Gibson's novel Neuromancer, in which Molly also appears.
The elephants from The Jungle Book are actually expies of the elephants from the animated shortGoliath II. In fact, all of the elephants' designs from this short were actually reused for this movie!
Little John from Robin Hood is an expy of Baloo from The Jungle Book. This was likely done so that Disney could save some money by recycling animation from The Jungle Book, as Robin Hood was made with a relatively shoestring budget. As a result of reusing the animation (which was dynamic and full of personality), Little John's personality wound up almost identical to Baloo's.
After The Lion King was a big success, Disney decided to make all their Funny Animal comic relief characters be total expies of Timon and Pumbaa. Examples include Tip and Dash (Timon and Pumbaa as a penguin and a walrus), Terk and Tantor (Timon and Pumbaa as a female gorilla and an elephant).
A lot of Disney characters are basically rehashes of previous characters. Take Lumière from Beauty and the Beast, Timon from The Lion King and Naveen the frog from The Princess and the Frog: they are all small arrogant know-it-alls. Lumière and Naveen even share the same bad French accent.
Young Billie "Buckwheat" Thomas reminded The Little Rascals producer Hal Roach so much of the series' former star Allen "Farina" Hoskins that his character was modeled after Farina's. Right down to the pigtails, Viewer Gender Confusion, and being named after a breakfast cereal.
In the Marx Brothers film each brother plays a character with a different name but the same personality as the character he played in the other films. As do some of the recurring supporting actors, most notably Margaret Dumont.
This films incarnation of Faora is closer to Ursa than the man-hating Faora from the comics. Recursive, as Ursa herself was a loose Expy of Faora.
A huge, non-verbal bruiser distinguished by his incredible strength and loyalty to Zod? Nam-Ek is this film's stand-in for Non.
Laurence Fishburne based his Perry White on 60 Minutes member Ed Bradley. Both even have a pierced ear.
Jenny was rumored to be a gender-flipped Jimmy Olsen, but the movie reveals her surname is "Jurwich" by the end (and high-resolution publicity shots showing her ID card will reveal this, too). Confusingly, a tie-in book does name her as "Jenny Olsen."
General Swanick is one for General Sam Lane (Lois' father), who has a prominent role in one of this film's sources, Superman: Secret Origin.
Sort of a type-casting example with Paul Bettany. He was in a biopic on Charles Darwin, and some reviews noted his previous role as Stephen Maturin in film Master and Commander who comes across as somewhat similar to Darwin in his time on the Beagle (intellectual naturalist on a ship, interacts with giant tortoises at one point).
David Lynch wrote Mulholland Dr. as a television pilot, and some believe a potential sequel to Twin Peaks. Lynch enthusiasts argue that the character of Betty/Diane in Mulholland Drive is an Expy of Audrey Horne on Twin Peaks.
Léon is Victor from Nikita. Same actor, and they even share an euphemism for their job, "cleaner". Luc Besson has said that they're basically cousins. (In Victor's case it's not a euphemism: his job is cleaning up after killers, not killing like Léon.)
Winston Wolf, "the cleaner" from Pulp Fiction, is an Expy of the character played by Harvey Keitel in The Point of No Return — which was itself a remake of Nikita, thus tying all of these fellas together.
Norman Bates of Psycho and David Callaway in Hide and Seek have similar characteristics. They are protagonists of their films, they fight antagonists not shown to us, they found out that they themselves are the antagonists, and they have a Split Personality Takeover afterwards.
In Return to Oz, Dorothy's new companions are not quite so different from her first companions from her first visit in Oz. Billina = Toto, Tik-Tok = the Tin Man, Jack = the Scarecrow, and the Gump = the Cowardly Lion. It verges into Suspiciously Similar Substitute territory, since these characters were also in The Marvelous Land of Oz and Ozma of Oz, which the movie was largely based on.
Hank Scorpio was originally going to be the villain of The Simpsons Movie, but instead, the movie has a different character, Russ Cargill. The two have the same voice actor (Albert Brooks), some of Cargill's lines sound like the kind of thing Scorpio might say, and both are pretty Bond-villainish.
Like the Hager example, Jessica Priest from Spawn was created to replace Chapel, since it turned out his rights were tied to Rob Liefeld's Youngblood franchise.
Star Wars, a lot of the characters from the Prequel Trilogy are expies of characters from the Original Trilogy (Even if both characters are actually in the original trilogy):
Anakin Skywalker in episodes II and III is basically an expy of his own son, even though he was also The Dragon in episodes IV, V, VI and even the end of III.
Qui-Gon Jin is The Obiwan TO Obi-Wan Kenobi, and is an expy of his own apprentice basically.
Darth Maul is obviously an Expy of Darth Vader in a The Dragon sort of way. Count Dooku is also an Expy of Darth Vader, but he's actually got more in common with The Emperor, and is more of a TheStarscream than a TheDragon. General Greivous is a bit closer to Vader; Darth Vader has trouble breathing, Grevious has a cough, and they're both cyborgs. Word of God says the three were used in foreshadowing, each one being an element of Vader. Maul as The Dragon who enforces the emperor's will, Dooku as a fallen Jedi, and Grievous as a cyborg with breathing problems (though he only got them after Mace Windu used the Force to crush his chest).
The Strangers with Candy film introduced Megawatti as an obvious expy for Orlando from the series because the actor who played him was too old to reprise the role.
Transformers II Revenge of the Fallen; In Transformers 1, of course, they couldn't have a giant robot turn into outdated '80s technology so they had an expy of Soundwave by taking one of Soundwave's tapes (Frenzy) and turning him into a CD player. In Revenge of the Fallen, they turn Soundwave himself into a satellite, and he sends another one of his tapes, Ravage, to Earth to spy on the humans. The whole Expy thing becomes a bit Meta, because Ravage spews a bunch of little metal balls which come together and form another character who is an expy of Movie 1's Frenzy!
John Cusack's Hitman with a Heart in War Inc. is an expy of his character in the earlier film Grosse Pointe Blank, and almost every other character in the new film has an equivalent in the previous one.
Wreck-It Ralph: All of the principal leads in the film are expies of video game characters in some way. Disney also got the rights to use actual video game characters for cameos rather than just expies, a la Who Framed Roger Rabbit and Toy Story. Ralph himself is basically a human Donkey Kong. The hero of the game, Felix, is an imitation of Mario (or, as he was called back in Donkey Kong, Jumpman).
Also, the names Fix-It Felix and Wreck-It Ralph are similar to that of obscure franchise Hammerin' Harry complete with similar catchphrases. And indeed, the beginning of the film shows Ralph's house getting demolished to make place for a series of apartments, which is exactly what happens to Hammerin' Harry at the beginning of the game. Observe.
The name may also be an allusion to Wrecking Crew, which starred a hammer-wielding Mario.
Sgt. Calhoun could be based on any number of commando characters from video games. But in particular she seems to be a cross between Samus and a ParagadeFemale Shepherd, with the language kept family-friendly.
She also has a lot of similarities to Captain Amelia from Treasure Planet. Both are Badass In Charge females, tough, snarky, are Tsundere, lost someone close to them (Amelia lost her closest friend, Mr. Arrow and Calhoun lost her fiancé, Brad), and they both fall in love with and marry Nice Guys who are bashful and Badass (Dr. Delbert with Amelia and Felix for Calhoun).
Sugar Rush at first seems like any other kart racing game from the '90s, only it's themed on candy. But Rich Moore stated that his favorite current game is Mario Kart, so we can assume that's the basic inspiration. Indeed, it seems like a cross between Mario Kart and Candy Land.
Portions of the Sugar Rush race course are clearly taken from various Mario Kart 64 courses, with the candy theme substituted in. The Fruit by the Foot-themed track where Turbo jumps Vanellope is very similar to Rainbow Road, for instance.
Turbo, in addition to being the name of a Sega arcade game, is basically a knock-off of the marquee chalky-skinned mascot from the Bally/Midway game Rally X.
His King Candy persona is one of The Wizard from The Wizard of Oz. He comes from another land (his own game), is leading his subjects on through manipulation and usurping the rightful ruler and having their memories locked away (Ozma and Vanellope), the hero comes to him for a favor (in Ralph's case, the medal he got from Hero's Duty), while he asks of something in return that involves the "villain" (Vanellope, which he calls "The Glitch", and smashing her candy car), and is ultimately a fraud hiding behind another image that makes the hero appreciate the things they have in life. Heck, there's even some cute allusions with the fact he's ruling over what can be considered Munchkins (the other candy racers) and has Oreo guards which chant in the same fashion as those from the movie.
His clothing is somewhat similar to Willy Wonka's, and of course they are both strongly associated with candy and sweets.
King Candy is also noted to have some unsettling similarities to Judge Doom due to both characters using disguises throughout the majority of their respective films and possessing unnerving true forms.
In the same way that King Candy is an Expy of The Wizard of Oz Vanellope can be seen as one for Princess Ozma in the sense that she's the rightful ruler of the kingdom and was ousted through trickery, and has no memory of who she really is. And like Ozma she's eventually restored to her rightful place.
The arcade owner, Mr. Litwak, looks a very great deal like Walter Day.
Those familiar with Warhammer 40,000 might notice how the Cy-Bugs are very similar to the Tyranids.
Fans of The Incredibles might liken Ralph and Calhoun to Bob and Helen, which makes it feel strange when they're not the ones to develop feelings for each other.