sitting pretty, adj. — Green’s Dictionary of Slang

sitting pretty adj.

1. (US) drunk.

1921

O.O. McIntyre New York Day by Day 8 Mar. [synd. col.] It used to be along Broadway a man over indulged and wanted to confess he would explode, ‘Boys, I’m tighter than a boiled owl.’ [...] Now he says, ‘Boys, I’m sitting pretty.’.

2. secure, safe, enjoying an easy life, esp. as to material things.

1920		R.J. Fry Salvation of Jemmy Sl. II i: Are you all sitting pretty now? Shall I shoot?
1924		Rosa Henderson ‘Twelth Street Blues’ 🎵 It’s just a year since I was settin’ pretty, / In my old home town down in Kansas City!
1929		J. Lait Broadway Melody 16: The Mahoney Sisters are sitting pretty on top of the world.
1930		J. Lait Put on the Spot 110: I got the office t’-day that we’re settin’ pretty.
1935		(con. 1920s) J.T. Farrell Judgement Day in Studs Lonigan (1936) 555: By then I hope we’ll be sitting pretty.
1937		R. Westerby Wide Boys Never Work (1938) 168: The world was like a mad-house if rotten blackguards could sit pretty while a chap who used his hands and his brains for productive work could only hope for as few quid a week.
1946		Mezzrow & Wolfe Really the Blues 87: I hear he’s sitting pretty now, with a big string of horses and a valet.
1953		A.J. Liebling Honest Rainmaker (1991) 48: When you are sitting pretty you should refrain from endangering your position.
1958		A. Sillitoe Sat. Night and Sun. Morning 190: They spoke of getting married in three months, by which time, Arthur said, they would have collected a good amount of money [...] so they would be sitting pretty.
1963		‘Nino Culotta’ Gone Fishin’ 9: If he had the dough for all the fish he’s given away, he’d be sitting pretty now.
1969		A. Buzo Rooted III iv: Me and Hammo, we’ll be sitting pretty, I’m telling you.
1977		(con. 1941) R. Beilby Gunner 83: What happened to the Kiwis? They looked to be sitting pretty yesterday.
1982		H. Beaton Outside In Act II: What about’cha? You’re sittin’ pretty, ain’cha?
1992		S. Armitage ‘Alaska’ in Kid 26: So you upped and went [...] Now you must be sitting pretty.
1999		Guardian G2 19 Oct. 5: Dobbo [...] took time off last week from his sitting pretty schedule.
2000		Indep. on Sun. 30 Jan. 19: Sitting pretty: Belinda Coote from Brighton who was awarded £195,000 compensation for being refused a reference.
2006		St Louis Post-Dispatch (MO) 26 Aug. B012/1: Before the kentucky Derby Holthus thought he was sitting pretty with Lawyer Ron.
2017		Houston Herald (MO) 2 Nov. A007/1: ‘He’s sitting pretty in the catbird seat’.