Odd Pairings

A list of movies with co-stars you might not think would be in the same scene let alone the same movie together. The oddness comes from actors of very different genres, eras, career arcs, star power, or a combo thereof.

I will add more as they become known. I invite any other input for inclusion.
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1.
Hang 'Em High (1968)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
When an innocent man barely survives a lynching, he returns as a lawman determined to bring the vigilantes to justice. (114 mins.)
Director: Ted Post
“ Clint Eastwood and Alan Hale, Jr., alias "the skipper" from Gilligan's Island.

Eastwood is no one's "little buddy", and he lets Hale's character know it. ” - carlsez_1
 
2.
The Dead Pool (1988)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
Dirty Harry Callahan must stop a sick secret contest to murder local celebrities, which includes himself as a target. (91 mins.)
Director: Buddy Van Horn
“ Clint Eastwood and Jim Carrey.

This is interesting because in his standup routine Carrey used to do an impersonation of Eastwood's Dirty Harry. Looking at Carrey's over-the-top rock star character makes you wish Dirty Harry would have made our day and shot him. ” - carlsez_1
 
3.
Sextette (1978)
    1 2 3 4 5 6 7 8 9 10 3.1/10 X  
Marlo Manners is enjoying her honeymoon with Sir Michael Barrington, husband number 6. As luck would have it... (91 mins.)
Director: Ken Hughes
“ Mae West and Alice Cooper.

There's only one thing that I can think of that could connect these two: both are outrageous. But a bombshell from the 30s performing with a shock rocker from the 70s? It's worth seeing just for that.

Actually, Mae West and half the cast sound like odd pairings, but Cooper's was the oddest. ” - carlsez_1
 
4.
Judgment at Nuremberg (1961)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
In 1948, an American court in occupied Germany tries four Nazi judges for war crimes. (186 mins.)
Director: Stanley Kramer
“ William Shatner and Spencer Tracy, Marlene Dietrich.

The Shats gives a modest and competent performance as the young actor holds his own between two screen legends. Include Judy Garland and you have 'Dorothy Gale meets Captain Kirk'. ” - carlsez_1
 
5.
Just You and Me, Kid (1979)
    1 2 3 4 5 6 7 8 9 10 6.0/10 X  
George Burns stars as a former vaudevillian who befriends a young runaway, played by 14-year old Brooke Shields, who is being chased by drug dealers. (93 mins.)
Director: Leonard Stern
“ George Burns and Brooke Shields.

Actually, the oddness was intentional; a popular child model/actor appearing with the venerable geriatric comedian. This singular premise is illustrated appropriately by the film's poster art: a little rib poke of fun! ” - carlsez_1
 
6.
Ragtime (1981)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
A young black pianist becomes embroiled in the lives of an upper-class white family set among the racial tensions, infidelity, violence, and other nostalgic events in early 1900s New York City. (155 mins.)
Director: Milos Forman
“ James Cagney and Fran Drescher.

Emerging straight from the golden age of cinema Cagney came out of semi-retirement to do his second-to-last movie. Almost any young actor would have looked a bit out of place next to him, let alone a character like Drescher. It would have been fun to see her nasal laugh silenced with a grapefruit halve shove to the face. ” - carlsez_1
 
7.
The Fighting Kentuckian (1949)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Following Napoleon's Waterloo defeat and the exile of his officers and their families from France, the U.S.Congress... (100 mins.)
Director: George Waggner
“ John Wayne and Oliver Hardy.

Wayne and Hardy were apparently good friends, and Hardy does a good job playing a more serious character, albeit still with some of his iconic comic mannerisms. Watching this I kept expecting to see a scene where they get their different sized coonskin caps mixed up. ” - carlsez_1
 
8.
Ironweed (1987)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
An alcoholic drifter spends Halloween in his home town of Albany, NY after returning there for the first time in decades. (143 mins.)
Director: Hector Babenco
“ Fred Gwynne and Meryl Streep.

Gwynne is a great dramatic actor, but will always be remembered as the flat-topped Herman Munster, which doesn't exactly strike me as inclusive to Streep's dramatic sphere. Although, her roles of late have been getting more fun and requiring extra make-up. I'd bet that she'd make a great Lilly should there be a Munster remake. ” - carlsez_1
 
9.
Showtime (2002)
    1 2 3 4 5 6 7 8 9 10 5.5/10 X  
A spoof of buddy cop movies where two very different cops are forced to team up on a new reality based T.V. cop show. (95 mins.)
Director: Tom Dey
“ Robert DeNiro and William Shatner.

DeNiro began showing up with a variety of costars that seemed to be pulled from differing cinema worlds. But having Shatner to play off of shows that he had reached a point where he could relax and have a little fun with his career. Actually it was Shatner who thrived specifically by poking fun at himself. It brought him broader recognition by costarring with a multiple Oscar nominee. It shows that taking control with your own self-parody is one way to successfully reinvent your career. ” - carlsez_1
 
10.
The Running Man (1987)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
A wrongly convicted man must try to survive a public execution gauntlet staged as a game show. (101 mins.)
“ Arnold Schwarzenegger and Richard Dawson.

Playing a TV host was an appropriate role for Dawson. But in this movie he had to affect a far more sinister style to pull it off. Was he a convincing nemesis to the Terminator? "Survey SAYS...." ” - carlsez_1
 
11.
The Freshman (1990)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Clark Kellogg is a young man starting his first year at film school in New York City. After a small time crook steals all his belongings... (102 mins.)
Director: Andrew Bergman
“ Marlon Brando and Matthew Broderick.

Broderick has since proven himself to be an accomplished actor from comedies to drama. He finds a middle ground with a little self-parody help from Brando. I still think the producers chuckled at the premise of pairing Vito Corleone with Ferris Bueller. ” - carlsez_1
 
12.
Tootsie (1982)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap. (116 mins.)
Director: Sydney Pollack
“ Dustin Hoffman and Bill Murray.

Murray was still the young self-assured goofball when he appeared with the veteran of more dramatic fare. A slightly offbeat comedy is a pretty good way to bring together these then unlikely costars. ” - carlsez_1
 
13.
Head (1968)
    1 2 3 4 5 6 7 8 9 10 6.6/10 X  
The Monkees are tossed about in a psychedelic, surrealist, plotless, circular bit of fun fluff. (86 mins.)
Director: Bob Rafelson
“ The Monkees and Victor Mature.

Hunky star of biblical dramas and film noirs gets to hang out with pre-fabbed pop group. I'll bet it looks as odd as it sounds. ” - carlsez_1
 
14.
The Elephant Man (1980)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A Victorian surgeon rescues a heavily disfigured man who is mistreated while scraping a living as a side-show freak. Behind his monstrous facade, there is revealed a person of intelligence and sensitivity. (124 mins.)
Director: David Lynch
“ David Lynch and Mel Brooks.

Who would believe the outrageous Brooks known for sometimes sophomoric comedy would collaborate with a young filmmaker known for bizarre images of Freudian guilt? Brooks was wise to not be credited for his role as producer in this serious black-and-white drama lest the audience get the impression that John Merrick might at any moment break into a rendition of 'Puttin' on the Ritz'. ” - carlsez_1
 
15.
Myra Breckinridge (1970)
    1 2 3 4 5 6 7 8 9 10 4.3/10 X  
Myron Breckinridge is waiting for her sex-change operation while a stoned surgeon stumbles into the operating room... (94 mins.)
Director: Michael Sarne
“ The whole cast list reads like one for a Love Boat episode. A veritable cavalcade of actors from multiple dimensions in the acting world. Three generations of sex symbols are represented by Mae West, Raquel Welch, and Farrah Fawcett. Future stars Tom Selleck and Dan Hedaya mix with classic Hollywood types Andy Devine and John Carradine. ” - carlsez_1
 
16.
X: The Man with the X-Ray Eyes (1963)
    1 2 3 4 5 6 7 8 9 10 6.7/10 X  
A doctor uses special eye drops to give himself x-ray vision, but the new power has disastrous consequences. (79 mins.)
Director: Roger Corman
“ Ray Milland and Don Rickles.

Rickles is a pretty good character actor, though it's pretty much one character. When he tones down his persona he has a more serious, even menacing presence (re: Casino). But at any moment I was ready to hear him throw out a 'hockey puck' insult.
(inclusion credited to 'Utopius') ” - carlsez_1
 
17.
Shadowboxer (2005)
    1 2 3 4 5 6 7 8 9 10 5.6/10 X  
When an assassin is diagnosed with terminal cancer, she decides to carry out one final killing, assisted by her lover and stepson, Mikey. (93 mins.)
Director: Lee Daniels
“ Cuba Gooding Jr. and Helen Mirren. Joseph Gordon-Levitt & Mo'Nique.

Gooding is the stepson AND the lover of Mirren, so I guess an odd pairing deserves an even odder plot setup. I can't seem to picture most anyone paired with Mo'Nique. I guess she's just too...U'Nique.
(inclusion credited to 'jerrellejames-1') ” - carlsez_1
 
18.
The Wackness (2008)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
It's the summer of 1994, and the streets of New York are pulsing with hip-hop. Set against this backdrop, a lonely teenager named Luke Shapiro spends his last summer before university selling marijuana throughout New York City, trading it with his unorthodox psychotherapist for treatment, while having a crush on his stepdaughter. (99 mins.)
Director: Jonathan Levine
“ Ben Kingsley & Mary-Kate Olsen.

Gandhi meets half the Olsen twins.
(inclusion credited to 'jerrellejames-1') ” - carlsez_1
 
19.
Extreme Measures (1996)
    1 2 3 4 5 6 7 8 9 10 6.1/10 X  
Thriller about Guy Luthan (Hugh Grant), a British doctor working at a hospital in New York who starts... (118 mins.)
Director: Michael Apted
“ Gene Hackman and Hugh Grant.

Both are dramatic actors and can do comedy, but I just don't see these two appearing together. Even the tones of their respective movie lists seem to clash. In my mind I keep seeing Popeye Doyle getting so irritated at Grant's befuddled charm that he ends up pistol whipping him.
(inclusion credited to 'yurenchu') ” - carlsez_1
 
20.
Silverado (1985)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A misfit bunch of friends come together to right the injustices which exist in a small town. (133 mins.)
Director: Lawrence Kasdan
“ Kevin Costner and John Cleese.

'Silly walk' meets silly apocalyptic film maker.
(inclusion credited to 'yurenchu') ” - carlsez_1
 
21.
Only the Lonely (1991)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
A Chicago cop must balance loyalty to his overbearing mother and a relationship with a shy funeral home worker. (104 mins.)
Director: Chris Columbus
“ John Candy and Ally Sheedy.

And as love interests no less. Also worth noting is Anthony Quinn and Maureen O'Hara. Try picturing them doing scenes with 'Ox' from Stripes.
(inclusion credited to 'darbyresearch') ” - carlsez_1
 
22.
The King of Comedy (1982)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Aspiring comic Rupert Pupkin attempts to achieve success in show business by stalking his idol, a late night talk-show host who craves his own privacy. (109 mins.)
Director: Martin Scorsese
“ Robert DeNiro & Jerry Lewis.

In contrast to his classic goofball characters Lewis could come off as a pretty serious guy. DeNiro seems to trade places with him and becomes the slightly goofy one.
(inclusion credited to 'ZevII') ” - carlsez_1
 
23.
Love Affair (1994)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
Ex-football star Mike Gambril meets Terry McKay on a flight to Sydney, which is forced to land on a small atoll... (108 mins.)
“ Katharine Hepburn and Garry Shandling.

Ms. Hepburn was such an iconic symbol of classic Hollywood that more than just Shandling seem a bit out of place next to her. ” - carlsez_1
 
24.
Five Easy Pieces (1970)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
A drop-out from upper-class America picks up work along the way on oil-rigs when his life isn't spent in a squalid succession of bars, motels, and other points of interest. (98 mins.)
Director: Bob Rafelson
“ Jack Nicholson and Sally Struthers.

Nicholson had made a name for himself in Easy Rider but was still not an Oscar darling when paired with the lesser known Struthers. Yet seeing a pre-Gloria Stivik with the iconic Jack was a bit of a surprise.

There's a rather spirited sex scene between the two, which was a slightly jarring image to deal with. What would you think if you came across, say, a movie with Rob "meathead" Reiner doing it with a young Meryl Streep? I hope you weren't eating your lunch while reading this. ” - carlsez_1
 
25.
Cast a Giant Shadow (1966)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
An American Army officer is recruited by Jews in Palestine to help them form an army. The surrounding... (146 mins.)
“ Not really any odd pairings, I was just not aware that Sinatra, Kirk Douglas, and John Wayne were all in a movie together. A tough guy test of wills showdown-fest. ” - carlsez_1