What actor has played the most different roles multiple times?

Yes. Oz did his thing in SESAME STREET PRESENTS: FOLLOW THAT BIRD, and again in THE ADVENTURES OF ELMO IN GROUCHLAND, each a feature film that grossed over $10 million in theaters: pathetic compared to the Muppet movies, but still passable.

Richard Harris (Dumbledore) in the “Harry Potter” series and the “Man Called Horse” Westerns.

Ian McKellen as Gandalf in the LOTR series and as Magneto in the X-Men movies.

Patrick Stewart as Professor X in the X-Men movies and as Captain Picard in the “Star Trek” movies.

Sylvester Stallone as John Rambo and Rocky Balboa.

Stallone was also in all three Expendables films.

Leading to one of my 13 yr old’s best lines. Saw an ad for Expendibles 3 on a bus bench, and quipped “this time, they team up to beat…arthritis

Antonio Banderas:

Gregorio Cortez - Spy Kids/Spy Kids 2/Spy Kids 3D
El Mariachi - Desperado/Once Upon a Time in Mexico
Puss in Boots - Shrek 2/Shrek the Third/Shrek Forever After/Puss in Boots
Zorro - The Mask of Zorro/The Legend of Zorro

Liam Neeson as Zeus, Aslan, Qui-Gon Jinn, Ra’s al-Ghul, and The Guy Who Doesn’t Have Much Money But What He Does Have Is A Very Particular Set Of Skills.

John Cleese as Q in a few Bond films and Nearly HEadless Nick in several Harry Potter films.

I see where Schwarzenegger, who was Conan and is the Terminator and has done various Expendables sequels, has announced the Twins sequel called – Triplets.

Does Andy Serkis count?

Gollum in multiple LotR movies;
Caesar in two Planet of the Apes movies;
Klaw in Age of Ultron and the upcoming Black Panther.

Warwick Davis:
Griphook & Flitwick in the Harry Potter movies (should count as two, really…)
Leprechaun in the Leprechaun movies
Wicket in the Star Wars movies

Mickey Rooney:
Gus in Night at the Museum & sequel
Bill in Bill and sequel
Andy Hardy in lots
Whitey Marsh in Boys Town & sequel
Mickey McQuire in way lots

Here’s a related question: What actor has played a United States president in the most unrelated movies? It can be a real one (Edward Herrmann as FDR) or a generic one (I think Harrison Ford and Morgan Freeman have both played multiple presidents). Helen Mirren has played a queen on film at least eight times.

I believe Ford and Freeman have only played the President once each, in Air Force One and Deep Impact.

Surprisingly, this puts them behind Robin Williams, who played two Presidents in four different movies.

Leslie Nielsen as Frank Drebin in the Naked Gun series, and as the President in the Scary Movie series.
Steve Martin in the Cheaper by the Dozen series and the Father of the Bride series.

Orlando Bloom in LOTR and in the “Pirates of the Caribbean” series.

You forgot his outings as Clouseau, which makes me respect you more.

Clint Eastwood as Dirty Harry, Philo Beddoe and The Man With No Name.

He was great as T.R. but sucky as Ike (and actually looked a little more like Truman!).

In the '80s, Steve Guttenberg kicked off the Police Academy movies, the Cocoon movies, and the Three Men And A Baby movies; just imagine what promise the '90s hold!

Charlton Heston has played his share of Presidents, and as per the OP I’ll note that he reprised his Planet of the Apes role in Beneath the Planet of the Apes, and reprised his Marc Antony role from Julius Caesar in Antony and Cleopatra, and reprised his role as Cardinal Richelieu from The Three Musketeers in The Four Musketeers.

(Once upon a time, Richelieu was Vincent Price – who reprised as Doctor Goldfoot, and as Anton Phibes, and as François Delambre, and as The Invisible Man.)