This post is written in conjunction with the Dynamic Duos in Classic Film blogathon hosted by Once Upon a Screen and the Classic Movie Hub.

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HOLIDAY (1938)

Katharine Hepburn had the privilege of playing with some of the best leading men of her day, from Humphrey Bogart to John Wayne. She is perhaps best known for the nine films she made between 1942 and 1967 with her long-term lover Spencer Tracy. Hepburn also worked with director and friend George Cukor on a remarkable ten movies, starting with her Hollywood début picture, A BILL OF DIVORCEMENT (1932), until THE CORN IS GREEN (1979) just a couple years before his death.

These two Hepburn teamings may be the most well-known, but we must not forget that Hepburn made four films with sex-pot Cary Grant before she ever met Tracy, and three of these four movies were directed by Cukor.

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BRINGING UP BABY (1938)

“[Grant] was fatter, and it this point his boiling energy was at its peak. We would laugh from morning to night.” (Hepburn, Me)

“[Grant] is personality functioning.” (Hepburn)

SS cary grant“[Hepburn] was this slip of a woman and I never liked skinny women. But she had this thing, this air you might call it, the most totally magnetic women I’d ever seen, and probably ever seen since. You had to look at her, you had to listen to her, there was no escaping her.” (Cary Grant)

Of the four movies Hepburn and Grant made together, two have become timeless classics: BRINGING UP BABY (1938) and THE PHILADELPHIA STORY (1940). The first film they made together was SYLVIA SCARLETT (1935). Although the picture failed at the time, it has become something of a cult classic, especially among the homosexual community, due to its edgy/comedic subject matter. HOLIDAY (1938) is generally acknowledged as one of Katharine Hepburn most underrated masterpieces. Like BRINGING UP BABY and PHILADELPHIA STORY, it has a brilliantly funny script, with more depth than the two more popular pictures.

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Hepburn and Grant get awkward in SYLVIA SCARLETT (1935)

SYLVIA SCARLETT (1935) [comedy, drama, romance, cult classic]
Directed by: George Cukor
Starring: Cary Grant, Brian Aherne, Edmund Gwenn
Writers: Compton MacKenzie (novel), Gladys Unger, John Collier, Mortimer Offner
Plot: When her father runs into some trouble with the law, Sylvia dresses like a boy so she can accompany him out of the country. They team up with a couple other misfits and travel as a small acting troupe. Confusion ensues when Sylvia falls in love with a young man who still thinks she’s a boy. The movie was supposed to be a comedy, but nobody laughed so it completely tanked at the box office. It’s a silly movie that doesn’t really make much sense, but it has it’s humorous bits. Hearing Cary Grant use his natural-born cockney accent makes the whole movie worth renting at least once! (Read my post about SYLVIA SCARLETT to learn more)
Margaret’s rating: 
6/10

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BRINGING UP BABY (1938)

BRINGING UP BABY (1938) [screwball comedy, romance]
Directed by: Howard Hawks
Starring: Cary Grant, Charles Ruggles
Writers: Dudley Nichols, Hagar Wilde
Studio: RKO Radio Pictures
Plot: Professor David Huxley wants to solicit one million dollars for his work at the museum, but when he meets zany socialite Susan Vance, his plans get turned upside down. She’s fallen head over heals in love with him and will do anything to stay with him, even if that includes chasing her aunt’s pet leopard all over the Connecticut countryside. I could watch this movie ten million times (and I probably have) and still laugh just as hard as I did the first time. (Read more)
Margaret’s rating: 10/10 (personal favorite)

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HOLIDAY (1938)

HOLIDAY (1938) [comedy, romance]
Directed by: George Cukor
Starring: Cary Grant, Lew Ayres, Edward Everett Horton, Jean Dixon
Writers: Philip Barry (play), Donald Ogden Stewart, Sidney Buchman
Studio: Columbia
Plot: Julia and Johnny met each other two weeks ago on vacation, fell in love and are now engaged to be married. But when he goes to meet her family, he learns a couple of things: 1.) she’s very rich – yay! 2.) she might not appreciate his dreams as much as he does – boo! 3.) she has a great sister who might just be a kindred spirit – yay? This screenplay deals with some heavy topics, like social class and economic status, while still being entertaining, witty, and lots of fun. It’s a thoughtful play with both humor and heart. One of my favorites. (Read more)
Margaret’s rating: 9/10
*nominated for Academy Award for best art direction

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THE PHILADELPHIA STORY (1940)

THE PHILADELPHIA STORY (1940) [comedy, romance]
Directed by: George Cukor
Starring: Cary Grant, Jimmy Stewart, Ruth Hussey, Roland Young, Virginia Weidler
Writers: Philip Barry (play), Donald Ogden Stewart
Studio: MGM
Plot: Tracy is about to marry her salt-of-the-earth fiance, but her ex-husband (Grant) shows up unexpectedly with a couple reporters (Jimmy Stewart and Ruth Hussey) and things start to shake up. This witty Phillip Barry was written for Hepburn and has been a smash since it first appeared on Broadway in 1939. It has become part of the canon of must-see classic films. I have never shown this to a group of friends with a unanimous approval. (Read more)
Margaret’s rating: 10/10
*won Academy Award for best actor (Jimmy Stewart), best screenplay; nominated for best leading actress, best supporting actress (Ruth Hussey), best director, best picture

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Final Analysis

The four films Cary Grant and Katharine Hepburn made together are among my very favorite classic movies. The two actors had an obvious chemistry that came across in all their movies. They seem to have had such a casual comfort level with each other that benefited their work and their friendship. It would have been nice to see more movies co-starring this dynamic duo. Thank you for reading my post. Make sure you check out the other entries for the Dynamic Duo Blogathon on Once Upon a Screen and the Classic Movie Hub!

Hepburn and Grant clown around during a radio broadcast of THE PHILADELPHIA STORY (1940)