Adversaries in more than one Movie or TV show

Cafe Society
1

Sean Connery as James Bond faced off against Robert Shaw as Red Grant in From Russia with Love in that famous fight aboard the Orient Express.

Sean Connery as Robin Hood faced off against Robert Shaw as the Sheriff of Nottingham in Robin and Marian.

Roger Moore as James Bond faced off against Christopher Lee as Scaramanga in the worse-than-it-should-have-been Man with the Golden Gun.

Roger Moore as Sir Wilfred Ivanhoe faced off against Christopher Lee as Sir Otto of the Rhine in “The German Knight”, an episode of the 1958 TV series Ivanhoe.

I’m sure there are plenty of others (Heck, I’m sure I could recall plenty of others), but none come to mind right off the bat.

Got any others to suggest?
Especially if they don’t involve James Bond.

2

One unusual case would be Demi Moore and Bruce Willis. While they were a real life couple, they only appeared in two movies together (and the second was after their divorce). But they were adversaries in both. In fact, Moore’s character kills Willis’ character in both movies.

3

James Cagney and Humphrey Bogart in several films: The Oklahoma Kid, Angels with Dirty Faces and The Roaring Twenties.

Bogart and Edward G. Robinson: Brother Orchid, Bullets or Ballots, Kid Galahad, and Key Largo

4

The Marx Brothers and Douglass Dumbrille in A Day at the Races and The Big Store.

Charlie Chaplin and Eric Campbell in numerous short subjects.

5

The Three Stooges and Vernon Dent.

6

And those movies are Mortal Thoughts and Charlie’s Angels: Full Throttle.

DeNiro and Pacino…

…famously only appear together in two movies and they are adversaries in both. **Heat **and Righteous Kill

ETA - spoilered because one reveals a bit of a twist.

7

Also, the Stooges and Bud Jamison

8

In the Hope and Crosby “Road” pictures, Anthony Quinn was often the bad guy.

9

I first thought of Errol Flynn and Basil Rathbone, then I got thinking and realized that Errol Flynn’s most common foe was Claude Rains.

They were on opposite sides on:

Prince and the Pauper
Robin Hood
Captain Blood
Sea Hawk

and others, I believe.

10

Walter Brennan and Jack Elam in The Far Country and Support Your Local Sheriff. In the former, Brennan was the good guy and Elam the bad guy; the the latter, their roles were reversed.

11

I’d like to keep clear of series, especially with recurring characters (It’s not impressive that Roger Moore as 007 faced off against Richard Kiel as “Jaws” in both The Spy who Loved Me and Moonraker). General combined troupes should be avoided, too. It’s also not that impressive that The Marx Brothers faced Sig Ruman in both A Night at the Opera and * A Night in Casablanca*.
Unrelated films, if you please, people.

12

Clint Eastwood uses a lot of the same actors over and over.

Bill “Squeal Like a Pig” McKinney was his main enemy, Redlegs, in “The Outlaw Josey Wales.” He was also one of the hapless bikers Clint kept beating up in “Every Which Way But Loose.”

13

Harrison Ford and Pat Roach.

Raiders of the Lost Ark
Indy vs. the Sherpa
Indy vs. the German mechanic

Temple of Doom
Indy vs. the Thuggee

Last Crucade
Indy vs. the Gestapo agent

Arnold Schwarzenegger and Sven-Ole Thorsen in pretty much every one of Arnold’s movies.
ETA: Yes, my name does come from Raiders of the Lost Ark.

14

Would Robert De Niro and Joe Pesci in Raging Bull, Goodfellas and Casino count? Their relationships turned quite adversarial at the end of all three movies.

15

Richard Kiel played at least two different but towering villains to Darren Macgavin’s Kolchak.

16

Also Christopher Lee vs. Peter Cushing.

17

Similarly, Denzel Washington was the good guy and Russell Crowe the bad one in Virtuosity, and the exact opposite in American Gangster.

18

Owen Wilson and Ben Stiller were rivals in both Zoolander and Meet the Parents.
Ben Stiller and Vince Vaughn palyed rivals in Starsky & Hutch and Dodgeball.

19

I feel a little odd mentioning this one, they are so disparate, but Liam Neeson and Ralph Fiennes played Oskar Schindler and Amon Goeth in Schindler’s List. Then they played rival gods Zeus and Hades in the, ah lesser, Clash of the Titans remake…

20

Bolo Yeung played a bad guy in two Jean-Claude Van Damme movies, Bloodsport and Double Impact.