Adjectives
Prison Escapes
Shakespeare Sets and The Play
Ends with Double "E"
Is Anyone A Doctor?
100

It frequently precedes "old age" & "for the picking"

Ripe

100

In classic movie fashion, Jeffrey McCoy escaped a Manhattan jail in 1983 climbing down 9 stories on a rope made of these

Bedsheets

100

Denmark

Hamlet

100

Jesus is sometimes referred to as "the man of" this place

Galilee

100

What's that? An otologist specializes in the treatment of these organs?

Ears

200

It can mean damaged from heavy use or coated in a mixture of flour & eggs for frying

Battered

200

In June 1962 Frank Lee Morris & the Anglin brothers floated on makeshift rafts away from this prison

Alcatraz

200

Scotland

Macbeth
200

This window-washing tool goes back to one used by sailors to swab decks

Squeegee

200

Step on up with this doctor who specializes in the treatment of foot problems

Podiatrist 

300

Call me a compulsive liar, but it really does mean "pertaining to disease"

Pathological

300

Black Liberation Army leader Joanne Chesimard broke out of a New Jersey jail in 1979 & fled to this island country

Cuba

300

An island, population until recently: 1

The Tempest

300

In this dice game, a large straight will get you 40 points

Yahtzee

300

Good news! This doctor who specializes in making & interpreting X-rays says nothing's broken

Radiologist

400

It's a 5-letter word meaning pertaining to Francis or Alexander IV, for example

Papal

400

In 1983 38 members of this "Army" broke out of Maze Prison, considered one of the most escape-proof in Europe

The IRA

400

Rome, BCE

Julius Caesar

400

A buzzing busybody

Bumblebee

400

It's the 15-letter word for the type of doctor who deals with the structure, functions & diseases of the eye

Ophthalmologist 

500

Going back to the Greek word for "womb", it can mean uncontrollably emotional or wildly funny

Hysterical

500

The film "The Great Escape" was based on a real escape from one of these German-named P.O.W. camps

A Stalag

500

The court of Athens, and the woods

Midsummer Night's Dream

500

The recorded ancestry, especially upper-class ancestry, of a person or family

Pedigree

500

Lungs & respiration are the breath of life for this doctor

Pulmonologist