A trick or prank like a monkey’s; mischief; buffoonery; tomfoolery; shenanigans.
‘Monkeyshines’ is an American coinage dating back to the early 19th century. It’s one of several phrases that compare human and simian playful behavior. We also use ‘monkey business,’ ‘monkey around,’ ‘more fun than a barrel of monkeys,’ ‘monkey see, monkey do,’ and so on. These phrases make being a monkey sound like more fun than it probably is. However, such descriptions probably arose because people watching monkeys thought they were funny. Sort of slapstick humor, one supposes. Indulging in monkeyshines isn’t serious business, though sometimes it’s used in a sarcastic way to refer to ethical or legal violations.
The website Quora says the phrase first appeared in 1828 (as “munky shines”) in a song by Thomas ‘Daddy’ Rice, a popular white comedian who performed in blackface. In the song, called Jump Jim Crow, Rice sings and dances in the role of an old plantation slave: “I cut so many munky shines, I dance de gallopade.” The gallop, or gallopade, was a 19th-century dance.
This song is where the term ‘Jim Crow’ came from, used in segregation and other discrimination against African-Americans. But the word ‘shine’ as an abusive term for a black person may not have had anything to do with Rice’s song.
The ‘shine’ in ‘monkeyshine’ is colloquial, also dating back to the early 19th century, with a number of meanings, such as ‘a party,’ or ‘a ruckus or commotion.’ It’s used in the phrase ‘take a shine to,’ or may simply mean ‘a trick or caper.’ Harriet Beecher Stowe used it this last way in Uncle Tom’s Cabin, 1852.
The origins of this ‘shine’ are uncertain. It might be related to the dialect terms ‘shindy’ and ‘shinty,’ both used to mean ‘commotion,’ and both those are related to ‘shinny,’ a game similar to field hockey dating back to the 17th century.
From the racist aspect, African American comics have been criticized by members of their race for ‘cutting monkeyshines’ in front of white people. Meaning, I would suspect, acting in a manner that would please the white folks, more specifically acting a fool or pandering to whites.
My mother, born in Britain, used it to refer to tricks or pranks, so the phrase obviously traveled across the Atlantic. It’s not a word I’ve ever used, perhaps because I don’t find monkeys funny.