Odd Pairings

by carlsez_1 | created - 19 Mar 2012 | updated - 05 Apr 2016 | Public

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)

M | 114 min | Western

62 Metascore

When an innocent man barely survives a lynching, he returns as a lawman determined to bring the vigilantes to justice.

Director: Ted Post | Stars: Clint Eastwood, Inger Stevens, Pat Hingle, Ed Begley

Votes: 30,135

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.

2. The Dead Pool (1988)

R | 91 min | Action, Crime, Mystery

46 Metascore

Dirty Harry Callahan must stop a sick secret contest to murder local celebrities, which includes himself as a target.

Director: Buddy Van Horn | Stars: Clint Eastwood, Liam Neeson, Patricia Clarkson, Evan C. Kim

Votes: 35,292 | Gross: $37.90M

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.

3. Sextette (1978)

PG | 91 min | Comedy, Musical, Romance

On the day of her wedding to her sixth husband, a glamorous silver screen sex symbol is asked to intervene in a political dispute between nations, which leads to chaos.

Director: Ken Hughes | Stars: Mae West, Timothy Dalton, Dom DeLuise, Tony Curtis

Votes: 1,075

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.

4. Judgment at Nuremberg (1961)

Not Rated | 186 min | Drama, War

60 Metascore

In 1948, an American court in occupied Germany tries four Nazi judges for war crimes.

Director: Stanley Kramer | Stars: Spencer Tracy, Burt Lancaster, Richard Widmark, Marlene Dietrich

Votes: 58,493

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'.

5. Just You and Me, Kid (1979)

PG | 95 min | Comedy

George Burns stars as a former vaudevillian who befriends a young runaway, played by fourteen-year-old Brooke Shields, who is being chased by drug dealers.

Director: Leonard Stern | Stars: George Burns, Brooke Shields, Lorraine Gary, Ray Bolger

Votes: 709

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!

6. Ragtime (1981)

PG | 155 min | Drama

57 Metascore

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.

Director: Milos Forman | Stars: James Cagney, Elizabeth McGovern, Howard E. Rollins Jr., Brad Dourif

Votes: 7,586 | Gross: $21.02M

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.

7. The Fighting Kentuckian (1949)

Passed | 100 min | Adventure, Romance, War

In 1818 Alabama, French settlers are pitted against greedy land-grabber Blake Randolph but Kentucky militiaman John Breen, who's smitten with French gal Fleurette De Marchand, comes to the settlers' aid.

Director: George Waggner | Stars: John Wayne, Vera Ralston, Philip Dorn, Oliver Hardy

Votes: 2,489

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.

8. Ironweed (1987)

R | 143 min | Drama

An alcoholic drifter spends Halloween in his home town of Albany, New York after returning there for the first time in decades.

Director: Hector Babenco | Stars: Jack Nicholson, Meryl Streep, Carroll Baker, Michael O'Keefe

Votes: 7,363 | Gross: $7.39M

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.

9. Showtime (2002)

PG-13 | 95 min | Action, Comedy, Crime

32 Metascore

A spoof of buddy cop movies where two very different cops are forced to team up on a new reality based television cop show, while tracking down the manufacturer and distributor of an illegally made semi-automatic firearm.

Director: Tom Dey | Stars: Robert De Niro, Eddie Murphy, Rene Russo, Rachael Harris

Votes: 56,504 | Gross: $38.08M

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.

10. The Running Man (1987)

R | 101 min | Action, Sci-Fi, Thriller

45 Metascore

A wrongly convicted man must try to survive a public execution gauntlet staged as a game show.

Director: Paul Michael Glaser | Stars: Arnold Schwarzenegger, Maria Conchita Alonso, Yaphet Kotto, Jim Brown

Votes: 126,389 | Gross: $38.12M

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...."

11. The Freshman (1990)

PG | 102 min | Comedy, Crime

A NYC film school student accepts a job with a local mobster who resembles a famous cinema godfather and who takes the young man under his wing, after demanding total loyalty.

Director: Andrew Bergman | Stars: Marlon Brando, Matthew Broderick, Bruno Kirby, Penelope Ann Miller

Votes: 17,100 | Gross: $21.46M

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.

12. Tootsie (1982)

PG | 116 min | Comedy, Drama, Romance

87 Metascore

Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap.

Director: Sydney Pollack | Stars: Dustin Hoffman, Jessica Lange, Teri Garr, Dabney Coleman

Votes: 86,744 | Gross: $177.20M

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.

13. Head (1968)

G | 86 min | Comedy, Fantasy, Musical

The Monkees are tossed about in a psychedelic, surrealist, plotless, circular bit of fun fluff.

Director: Bob Rafelson | Stars: Peter Tork, Davy Jones, Micky Dolenz, Michael Nesmith

Votes: 5,081

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.

14. The Elephant Man (1980)

PG | 124 min | Biography, Drama

77 Metascore

A Victorian surgeon rescues a heavily disfigured man who is mistreated while scraping a living as a side-show freak. Behind his monstrous façade, there is revealed a person of intelligence and sensitivity.

Director: David Lynch | Stars: Anthony Hopkins, John Hurt, Anne Bancroft, John Gielgud

Votes: 193,194

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'.

15. Myra Breckinridge (1970)

R | 94 min | Comedy

After undergoing gender reassignment surgery, an aspiring actress travels to Hollywood, where she also wants to make a claim on her wealthy uncle's estate.

Director: Michael Sarne | Stars: Mae West, John Huston, Raquel Welch, Rex Reed

Votes: 2,490 | Gross: $3.00M

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.

16. X: The Man with the X-Ray Eyes (1963)

Not Rated | 79 min | Horror, Sci-Fi, Thriller

A doctor uses special eye drops to give himself x-ray vision, but the new power has disastrous consequences.

Director: Roger Corman | Stars: Ray Milland, Diana Van der Vlis, Harold J. Stone, John Hoyt

Votes: 5,211

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')

17. Shadowboxer (2005)

R | 93 min | Action, Crime, Drama

33 Metascore

When an assassin is diagnosed with terminal cancer, she decides to carry out one final killing, assisted by her lover and stepson, Mikey.

Director: Lee Daniels | Stars: Cuba Gooding Jr., Helen Mirren, Vanessa Ferlito, Macy Gray

Votes: 6,279 | Gross: $0.37M

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')

18. The Wackness (2008)

R | 99 min | Comedy, Drama, Romance

61 Metascore

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.

Director: Jonathan Levine | Stars: Josh Peck, Ben Kingsley, Olivia Thirlby, Famke Janssen

Votes: 28,731 | Gross: $2.08M

Ben Kingsley & Mary-Kate Olsen.

Gandhi meets half the Olsen twins. (inclusion credited to 'jerrellejames-1')

19. Extreme Measures (1996)

R | 118 min | Crime, Drama, Mystery

A young doctor confronts with a famous colleague, when he learns about the true methods of his work.

Director: Michael Apted | Stars: Hugh Grant, Gene Hackman, Sarah Jessica Parker, David Morse

Votes: 15,590 | Gross: $17.31M

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')

20. Silverado (1985)

PG-13 | 133 min | Action, Crime, Drama

64 Metascore

A misfit bunch of friends come together to right the injustices which exist in a small town.

Director: Lawrence Kasdan | Stars: Kevin Kline, Scott Glenn, Kevin Costner, Danny Glover

Votes: 32,237 | Gross: $33.20M

Kevin Costner and John Cleese.

'Silly walk' meets silly apocalyptic film maker. (inclusion credited to 'yurenchu')

21. Only the Lonely (1991)

PG-13 | 104 min | Comedy, Romance

A Chicago cop must balance loyalty to his overbearing mother and a relationship with a shy funeral home worker.

Director: Chris Columbus | Stars: John Candy, Maureen O'Hara, Ally Sheedy, Kevin Dunn

Votes: 8,908 | Gross: $21.83M

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')

22. The King of Comedy (1982)

PG | 109 min | Comedy, Crime, Drama

73 Metascore

Aspiring comic Rupert Pupkin attempts to achieve success in show business by stalking his idol, a late night talk-show host who just craves his privacy.

Director: Martin Scorsese | Stars: Robert De Niro, Jerry Lewis, Diahnne Abbott, Sandra Bernhard

Votes: 64,428 | Gross: $2.50M

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')

23. Love Affair (1994)

PG-13 | 108 min | Comedy, Drama, Romance

55 Metascore

Ex-football star Mike Gambril meets Terry McKay on a flight to Sydney, which is forced to land on a small atoll. Both engaged to others, they become romantic on board the ship sent to take ... See full summary »

Director: Glenn Gordon Caron | Stars: Warren Beatty, Annette Bening, Katharine Hepburn, Garry Shandling

Votes: 4,058 | Gross: $18.25M

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.

24. Five Easy Pieces (1970)

R | 98 min | Drama

85 Metascore

A dropout 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.

Director: Bob Rafelson | Stars: Jack Nicholson, Karen Black, Billy Green Bush, Fannie Flagg

Votes: 29,192

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.

25. Cast a Giant Shadow (1966)

Approved | 146 min | Adventure, Drama, History

In 1947, following the U.N. decision to split British Palestine into separate Jewish and Palestinian states, a former U.S. Army officer is recruited by the Jews to reorganize the Haganah.

Director: Melville Shavelson | Stars: Kirk Douglas, John Wayne, Frank Sinatra, Senta Berger

Votes: 2,431

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.



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