1920's
1930's
1940's
1950's
1960's
100

The bee's knees

excellent; outstanding 

100

Blow your wig

To get excited about something. Depictions of flying wigs and toupees was common in cartoons.

100

Blockbuster

a huge success 

100

Big brother is watching you

someone of authority is monitoring your actions

100

Hippie

derived from hipster; a young adult who rebelled against established institutions

200

Speakeasy

a place where alcohol was illegally sold and drunk during Prohibition

200

I'll be a monkey's uncle

sign of disbelief; I don't believe it!

200

Cheesy

Cheap

200

Boo-boo

a mistake; a wound

200

Groovy

cool; hip; excellent

300

Hotsy-totsy

Perfect

300

Make tracks

To leave quickly. This is a nod to a time when trains were the fastest way to get around.

300

Keeping up with the Jones's 

competing to have a lifestyle or socioeconomic status comparable to one's neighbors

300

Hipster

 an innovative and trendy person

300

The Man

a person of authority; a group in power

400

Gams

Legs

400

Bumping gums

Talking nonsense. This one really deserves a comeback, because it just rolls off the tongue.

400

Bust your chops

Used as a scolding, maybe to yell, but not to literally hit someone

400

Hi-fi

high fidelity; a record player or turntable

400

Daddy-o

a man; used to address a hipster or beatnik

500

Moll

a female companion of a gangster

500

Girl Friday

a secretary or female assistant

500

Keeping up with the Joneses

Keeping up with the Joneses -- competing to have a lifestyle or socioeconomic status comparable to one's neighbors

500

cop a breeze

to leave

500

Chrome dome

Bald man