Wiseguy
A wiseguy is a member of the Mafia or organized crime—the insider term mobsters use for themselves: He's a made wiseguy in the Gambino family.
More broadly, wiseguy means a smart aleck or someone who makes clever, often annoying remarks: Some wiseguy in the back kept interrupting the lecture.
The criminal sense dominates in American usage, popularized by mob films and memoirs.
1990 gangster film
- gangsterCriminal organization member
- mafiaCriminal organization using intimidation
- made manInitiated organized crime member
- capoString-shortening clamp device
informant · witness protection · wiseguys · rat · Henry Hill · mob · associate · button man
Goodfellas
1990 gangster film
- gangsterCriminal organization member
- mafiaCriminal organization using intimidation
- made manInitiated organized crime member
capo · informant · witness protection · wiseguys · rat · Henry Hill · mob · associate · button man · earner
smartass
Annoyingly glib person
sarcasm · lip · sass · flippant · mouthy · insolent · joker · wit · impudent · retort
con man
Fraud through false trust
operator · street smart · cunning · scammer · swindler · fast-talker · sharpie · grifter · charlatan · shrewd
Wiseguycop
Law enforcement slang
FBI agent · straight arrow · informant · civilian · square
Wiseguystraight shooter
Forthright, blunt person
naif · innocent · simple soul · rube · easy mark
wise, guy, wisdom, wisely, wiser, wisest, unwise, guys, wisecrack