starliteyes

Once Upon a Honeymoon

Eve Arden was in Comrade X with Clark Gable.

Ann-Margret

When Harry Met Sally, Irene and Mary Poppins

No, the movie is a drama and the star and director were once romantically involved.

The Sound of Music in My Heart

That Certain Age of Innocence

Peter Falk

Debra Winger was in Urban Cowboy with John Travolta.

Midnight Mary

Macauley, Homer - Mickey Rooney in The Human Comedy

(The) King and Four Queens

Pullman, Bill

Ruth Hussey was in The Uninvited with Ray Milland.

Bad Little Angel

Yeah, how about them? You got it, Miles. Your thread.

Hint: In the second film, they played brothers.

Gloria DeHaven was in Best Foot Forward with Virginia Weidler.

Franchot Tone

Ziegfeld Girl

Granville, Bonita

Jean Harlow

Ricardo Cortez was in Behind Office Doors with Mary Astor.

No, earlier movie from the previous decade. Another hint: The director encouraged the star to see the performance of the well known Broadway actress who originated the role. Although reluctant, she did it and immediately regretted it because she realized that she was now forced to play the part in a very different manner.

Kiss Them For Me and My Gal