Same First & Last Letter
Road Trip "I Spy"
Threesomes
I Want my "M"TV
"NN"YTIME
100

Prancer & Cupid were famous ones

reindeer

100

I spy...
Area 51,
Burning Man festival &
the Bellagio Hotel & Casino

Nevada

100

Game theorists might call it a "zero-sum game without perfect information"; those playing it to break a tie sometimes call it "Rochambeau"

rock, paper, scissors

100

Ad executive Draper Daniels was the inspiration for the name of this drama's lead character, Don Draper

Mad Men

100

In one word, not guilty

innocent

200

In 2017 the maximum length of this went from 140 to 280 characters

tweet

200

I spy...
Mount Washington,
Lake Winnipesaukee
& Dartmouth College

New Hampshire

200

If your clothing catches fire (though hopefully it won't), this 3-pronged fire safety mantra will remind you what to do

Stop, drop and roll

200

This show's 1983 finale "Goodbye, Farewell and Amen" is still the most watched episode of scripted TV ever

M*A*S*H

200

In the 1970s these department store models for clothing displays began to have belly buttons

mannequins

300

A short bit of praise from a critic or a fellow author on the cover of a book

a blurb

300

I spy...
Pikes Peak,
the John Denver Sanctuary &
Red Rocks Amphitheatre

Colorado

300

According to the carol, it's what "my true love gave to me" on the third day of Christmas; I just hope he wasn't regifting

Three french hens

300

Tipping his hat to Tom Selleck, Jay Hernandez wore a Detroit Tigers cap on the first episode of this reboot set in Hawaii

Magnum, P.I.

300

Born in the '80s & early '90s, they're often depicted as tech-savvy & maybe just a bit entitled

millennials

400

Larry Bird, or currently, Jayson Tatum

a Celtic

400

I spy...
Powell's City of Books,
Crater Lake National Park &
Timberline Lodge

Oregon

400

If "American Pie" is your karaoke go-to, you know they're "the three men I admire most" who "caught the last train for the coast

Father, Son and the Holy Ghost

400

Bryan Cranston said if this Fox sitcom had been renewed for one more season, he wouldn't have been available to play Walter White

Malcom in the Middle

400

This verb can mean to have your hiking companion for dinner, or to take resources from one project to finish another

cannibalize 

500

A fancy design of your initials that you use on stationery or clothing

A monogram

500

I spy...
the "American Gothic" house,
the future birthplace of James T. Kirk &
the "Field of Dreams" movie site

Iowa

500

Unlike women, these three "unalienable rights" are specifically mentioned in the Declaration of Independence

life, liberty and the pursuit of happiness

500

This TV character inspired a verb meaning, roughly, to make or repair something with what is conveniently on hand

MacGyver

500

"Astrophel and Stella" is a 16th century sequence of more than 100 of these 14-line poems

sonnets