1934, Investigation of Air Mail and Ocean Mail Contracts: Hearings before a Special Committee on Investigation of Air Mail and Ocean Mail Contracts, United States Senate, Seventy-third Congress, Second Session, pursuant to S. Res. 349 (72d Congress), a Resolution Creating a Special Committee of the Senate to Investigate Air Mail and Ocean Mail Contracts, Washington, D.C.: United States Government Printing Office, OCLC1284238, page 2804:
Part of that memorandum of Mr. Hanshue's refers to directors sitting pretty in thinking they were all set for certain benefits.
1973 July 20, “People in the News”, in Time, archived from the original on 14 December 2008:
Lauren Hutton, 28, was sitting pretty. The omnipresent model had just signed a two-year, $200,000 contract.
That's not a threat, sir, for they have played fair with me, and I sha'n't sacrifice a penny of their money—unless they force me to do so. But—I'm in control. I'm sitting pretty. They can't unseat me, and I warn them not to try.
2010, Donald O'Donovan, “The Golden Age: From the Novel Orgasmo”, in The Sugarhouse: A Novella: Plus Four Novel Excerpts from Orgasmo; Night Train; Confessions of a Bedbug Hauler; Tarantula Woman, [s.l.]: Open Books:
We were both sitting pretty back then, back in the 20th Century.