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Wiktionary
sitting pretty

a. 1 (context idiomatic English) Having a comfortable or certain supply of money or resources. 2 (context idiomatic English) In a favorable situation, especially a situation in which one possesses an advantage.

Wikipedia
Sitting Pretty (1948 film)

Sitting Pretty is a 1948 American comedy film which tells the story of a family who hires a man, Lynn Belvedere, with a mysterious past to babysit their children. It stars Robert Young, Maureen O'Hara and Clifton Webb. The movie was adapted by F. Hugh Herbert from the comic novel Belvedere (1947) by Gwen Davenport. It was directed by Walter Lang.

The character of Belvedere proved so popular, Webb reprised his role in two more movies: Mr. Belvedere Goes to College (1949) and Mr. Belvedere Rings the Bell (1951).

Sitting Pretty

Sitting Pretty or Sittin' Pretty may refer to:

Sitting Pretty (1933 film)

Sitting Pretty ( 1933) is an American Pre-Code musical comedy film telling the story of two aspiring, but untalented, songwriters, played by Jack Oakie and Jack Haley. They are joined by Ginger Rogers and Thelma Todd on their trip from New York to Hollywood to find their fortune. This film was directed by Harry Joe Brown and featured the Pickens Sisters as themselves.

Sitting Pretty (TV series)

Sitting Pretty is a 1992 BBC television sitcom written by John Sullivan. The series starred Diane Bull, David Ashford and John Cater and was directed by Susan Belbin and Angela De Chastelai Smith.

The series followed the travails of a woman whose millionaire husband dies suddenly. She discovers that her husband's will has left her penniless and she is forced to move back in with her parents and sister on their farm.

The lead role was originally intended to be played by a male lead, but was changed to become the first Sullivan sitcom to feature a female lead since Just Good Friends. However, John Oliver notes that it is also remembered as the writer's first notable failure.

Usage examples of "sitting pretty".

Witch of the East-you know that's what they called her, don't pretend to be so shocked-and I have a stronghold in the West, and I seem to have rallied the Arjikis around me, by dint of the absence of their ruling family-and there you are, sitting pretty in the North with your bank accounts and your legendary skills at sorcery.

There was a loud creaking sound that nearly gave me a heart attack, but then she was down and sitting pretty as can be as the sun broke over the horizon and the first red rays shone on 2Loose's masterpiece.

Okay, not a million dollars, but enough to keep you sitting pretty for the rest of your life.

Next thing you know, old Morrie is sitting pretty with the liftman's job at the Age in his pocket.

Great slugs, their parents' insurance had left them sitting pretty, didn't it?