OP specified not the same work, but the same character in different works.
Sean Connery played James Bond first in Dr. No in 1962 and for the last time in Never Say Never Again in 1984 22 years (for an action role!). If you count voice-only work, he voiced Bond anew in the video game From Russia With Love in 2005, for 43 years.
**Herbert Lom[/Bplayed police commisioner Charles Dreyfus first in A Shot in the Dark in 1964 (He apparently wasn’t in The Pink Panther), and played him in many of the sequels until 1993’s Son of the Pink Panther. He apparently wasn’t in the remake, so he’s never been in “THe Pink Panther” directly, but he spent 29 years playing the same caracter in sequels.
He also played Napoleon twice, 14 years apart , in The Young Mr. Pitt in 1942 and War and Peace in 1956. They should get bhim to fo it again, and hje’d break the record.
William Daniels has a lock on the Adams faily – the historical ones. He’s famous for playinmg John Adams in 1776 in 1972 (and since at least 1970 on Broadway) and in The Rebels (1978) and Sam Adams in and The Bastard (1979). But he gets the longevity award for playing John Qyuincy Adams in Hallmark Hall of Fame – A Woman for the Ages in 1952 and again in The Adams Chronicles in 1976. That’s 24 years.
Jack Lemmon and Waltter Matthau played Oscar Madison and FElix Unger in The Odd Couple in 1968 and **The Odd Couple II ** in 1998 – 30 years (Matthau played him longer on stage, although Art Carney started the role of Felix).
Tony Randall and Jack Klugman did the same roles from 1970 to 1993 (The Odd Couple: Together Again.
If you’re just looking at cameos, Kevin McCarthy appeared as Dr. Miles J. Bennell in the 1956 Invasion of the Body Snatchers, essentially reprised the part in the 1978 version, then did it again in Looney Tune: Back in Action in 2003, a total gap of 47 years.
Hal Holbrook has been playing Mark Twain for fifty years.
Beat that!
I know that we’ve discounted voice work, but I have to mention Mae Questel, who first did Betty Boop in 1930’s Dizzy Dishes, and last did her in 1988’s Who Framed Roger abbit – a total of 58 years. She wasn’t the first or only Betty Boop, but she was easily the most famous.
She also voiced Olive Oyl from 1933 through 1957
John Carradine played Dracula in the movies from 1944 to 1979 – 35 years. But he did the role on stage for longer, although I can’t find cites.
Pardon me, ma’am, but… have you forgotten Peter Falk?
34 years later, **elisha Cook, Jr. ** and Lee Patrick reprised their roles from The Maltese Falcon in The Black Bird.
Vera Miles and Anthony Perkins reprised their roles from Psycho (1960) in Psycho II (1983). Perkins would go on playing Norman Bates until **Psycho IV ** in 1990, for a total of 30 years.
Paul Newman played Eddie Felson in 1961’s The Hustler and 1986’s the Color of Money, 22 years apart. Walter Tevis wrote both.
Come to think of it, both the Star Wars and Star Trek franchises kept a lot of actos employed in the same roles for long periods. Peter Mayhew, Anthony Daniels, Kenny Baker, and the voice of James Earl Jones appeared in the 1977 original and in the last, **Revenge of the Sith ** in 2005 (28 years) , with lots of other actors working on several between.
Al Lewis ke[t playing his “Grampa Munster” character (or copyright-avoiding variations on it) for year after the TV show The Musters (started 1964) up through 1995.
He also reappeared as Leo Schnauser from Car 54 Where Are You? the movie in 1994, 33 years after originating the role on the TV show in 1961.
June Foray (voice again) did “Granny” in Warner Bothers cartoons from at least 1953 (and possibly 1943 – she did “Granny” in “Hiss and Make Up”, but I;m not sure it’s the same Granny) through 2005. And she;s still around – she can keep on doing it. That’s 52 or possibly 62 years.
She’s also done Rocket J. “Rocky” Squirrel from 1959 through 2000, and can keep on doing that.
Raymond Burr did Perry Mason from 1957 to 1993, for 36 years. He also played Steve Martin in Godzilla (1956) and Godzilla 1985, 29 years apart.
The bunch from The Dick Van Dyke Show (1961) reappeared together many times, most recently in 2004 with The Dick Van Dyke Show Revisited, with the following reprising their roles:
Dick Van Dyke
Mary Tyler Moore
Rose Marie
Carl Reiner
Larry Mathews
Ann Morgan Guilbert
Jerry Van Dyke
(Morey Amsterdam had appeared in previous get-togethers, but he was dead by then)
That’s 43 years for much of the original cast.
(By the way, Daws Butler bragged that when they got together to do new episodes of The Jetsons, they were the only show to regroup after so long a time with the entire original cast. That’s 1962 to 1987, for 25 years. For the 1990 movie, some voices were changed.)
Does it count if you voice the restored audio for your own movie? Tony Curtis did that for the 1991 restoration of the 160 movie Spartacus, and Peter O’Toole and others did it for 1989 restoration of the 1962 film Lawrence of Arabia.
Gee whiz, are you guys all slipping? Nobody brought up that Cloris Leachman also reprised her role for that episode, as Anthony’s mother? That was the more amazing part for me.
Keeping it to the films, Desmond Llewelyn has him beat. From the same series, he played Q from 1964 (Goldfinger) until his death in 1999 (The World is Not Enough). 35 years of gadgety goodness.