Definitions
American Heritage® Dictionary of the English Language, Fourth Edition
- n. A pirate.
- n. A pirate ship.
- n. See picaro.
- v. To act as a pirate.
Century Dictionary and Cyclopedia
- n. A rogue or cheat; one who lives by his wits; an adventurer.
- n. A plunderer; especially, a plunderer of wrecks; a pirate; a corsair.
- n. An instrument like a boat-hook, used in mooring logs or deals.
- n. A small pirate ship; a privateer or corsair.
Wiktionary
GNU Webster's 1913
- n. One who plunders; especially, a plunderer of wrecks; a pirate; a corsair; a marauder; a sharper.
Etymologies
- Spanish picarón, augmentative of pícaro, picaro; see picaro.
Examples
“BLOCK: Thoughts from public radio's picaroon of drollery, Brian Unger.”
“Janet looked at him with the sly simplicity of her sect, and replied, “Notwithstanding thy boasted honesty, friend, and although I am not accustomed to read and pass judgment on such volumes as thou hast submitted to my perusal, I think I see in thy countenance something of the pedlar-something of the picaroon.””
“Off the island of Planoca it was overpowered and captured by a little picaroon, with lateen sails and a couple of guns, and a most villainous crew, in poverty-stricken garments, rusty cutlasses in their hands and stilettos and pistols stuck in their waistbands.”
“As to the picaroon or privateer, she was able to do little in the matter, not daring to come so near the men-of-war as to take a broadside, which her thin sides would not have been able to bear, but would have sent her to the bottom at once; so that the English men-of-war had no assistance from her, nor could she prevent the taking the two merchant-ships.”
“_Athenæum_ necrologist accorded her half a column of obituary, in which she was described as "this pretty, picaroon woman, whose name can never be omitted from any chronicle of Bavaria.”
“I stopped 'em back there a ways with my picaroon, when they sung out, an 'they walked down here on the side planks.”
“Oram, the intrepid flume-herder, laughed, dug his picaroon into a log, and asked:”
“The space-axe -- a combination and sublimation of battle-axe, mace, bludgeon, and lumberman's picaroon, a massively needle-pointed implement of potentialities limited only by the physical strength and bodily agility of its wielder.”
Galactic Patrol
“But if one is insane, if one has inherited one's grandfather's characteristics as idler, loafer, lounger, dreamer, lover or picaroon, what then?”
“Salmon began to fall on the deck, heaved up on a picaroon.”
Lists
These user-created lists contain the word ‘picaroon’.
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Very Silly Words
A list of very silly sounding words, as well as words that are fun to say
badot, gardyloo, dingbat, gaffer, kine, haberdashery, forsooth, whey-faced, hoddypeak, brouhaha, widdershins, decemnovenarianize and 115 more...
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Pirate Tango
Apparently a group of pirates is called a "tango."
pirate, harbor-pirate, swashbuckler, buccaneer, corsair, rover, sea-rover, sea-robber, sea wolf, sea-rat, water-thief, picaroon and 9 more...
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He Goes a-Pickarooning
Here be a trove of words and phrases associated (fore or aft) with picarooning / pickarooning, scavenged from Google Books citations.
The Prince Edward Island folksong Mick Riley inspi...wagabone, privateer, at every corner, up and down, pirate, expeditions, life, look, rascals, expedition, literary, adventurers and 53 more...

madmouth interesting etymology, leading ultimately to pique Jun 15, 2009
sionnach Pick a rrroon! Any rrroon! Apr 9, 2009
bilby How lucky you arrrrr! Apr 9, 2009
jonasword My Gr 12 girlfriend introduced me to this word for pirate Apr 9, 2009