Caboose

When on road trips, my friends, family, and I occasionally play a fun game we call Caboose. I'm not sure where it comes from since a quick googling revealed nothing, but it's enough of a kick to share with others. It combines spelling, memory, strategy, and vocabulary, and for us at least often sparks other conversations around the core game, which is part of the point.

The basic idea

Players create long "trains" of words, trying to neither repeat words nor end the train. Players create trains by speaking words in turn whose first letters are the same as the last letter of the prior word. For example: "slate" could be followed by "egret", "eyot", "evince" or any word beginning in "e." Since trains (archetypically) end with a caboose, if a player speaks a word ending with the letter "c," e.g. "archaic", the next player speaks the word "caboose," which ends the current train. In this case, the player who ended a word with "c" is punished, not the one who spoke "caboose."

To be extremely explicit, a very short example of a train follows.

engine - estuary - yeoman - nether - row - wander - rich - helic (oops) - caboose

Depending on the chosen options for the game as well as the number and skill of players, games can last between 15 minutes and 2 hours. The minimum number of players is two. The maximum number of players is only limited by pragmatic concerns, such as ability to hear one another.

What you'll need

The basic version of the game can be equipmentless. That said, certain things are made easier with certain stuff. Arbitration can be made easier with a dictionary. Markers (discussed below under Options) can help keep score, and these can be anything you have handy. Paper and pen/pencil are needed if you have a documentarian.

Beginning the game

Players establish an order. We like to establish the person with the next birthday (a strategy happily borrowed from the board game Cranium™) as the first player and continue clockwise. The first player speaks the word "engine" and the second player begins from there.

Winning the game

Each player begins the game with three "lives." The last player with one or more lives remaining wins the game. A player loses a life in one of three ways.

A player repeats a word that has already been spoken in the current train.
A player speaks a word that doesn't chain correctly, e.g. following "milo" with "wan."
A player speaks a word that ends in the letter "c." Note that this omits the 5.13% of English words ending in c and the 8.62% of words that begin with c from being used.

Rules

These may look like a lot, but most of them are intuitive, and those that aren’t are edge cases that help mitigate the many-to-many relationships of the complex idea--word--sound combinations in human language.

Legal words

Only single words are permitted. Contractions, word phrases, and acronyms are not permitted.
Proper nouns are not allowed. Players accidentally using proper nouns are not penalized, but must select a new word.
Non-English words (or whatever the chosen language) are not allowed. Players accidentally using non-English words are not penalized, but must select a new word. Since the "foreignness" of a word can be in question, e.g. "biscotti", it is useful to have a dictionary on hand that acts as the final arbiter. In the absence of a dictionary, we rely on a few convincing arguments followed by a vote.
Alternate spellings are permissible, such as "theatre" and "theater" as long as they are still accepted English spellings. Such spelling variances adhere to the rules of homophones, above.
Simple homonyms such as "quail" the verb and "quail" the noun, and homographs are disallowed in the same train.
Homographs such as "bow" the verb and "bow" the noun, are disallowed in the same train.
Each meaning-spelling of a homophone may be used in the same train. For example, if the word "right" was already used in the current train, the word "write" is still permissable.
Keep Going
If a word is repeated, the offending player loses a life, but the word still counts. The next player must still chain to the repeated word.
If a word is chained incorrectly, as in the "wan" example above, the offending player loses a life, but again, the word still counts. The next player must still chain to the spoken word.
If a player speaks a word that ends in "c", that player loses a life. The next player says "caboose," ending the current train. If more than one player has a life reminaing, the next player speaks the word "engine" beginning a new train. All words which were spoken in the prior train are eligible for use again in the new train.
Homo(phone) Rights
A player may ask for the prior word to be defined or used in a sentence that clarifies its meaning. This is especially useful if the word is a homophone.
A player using a homophone must intend a particular spelling. If the next player does not recognize the word as a homynm but still chains the word according to the spelling intended by the prior player, there is no penalty. We use the honor system for enforcement. Alternately, if a player recognizes a prior word as a homophone, that player may ask the prior player to whisper the intended meaning to another person. If only two players are present, the homophone-speaking player may be asked to write the intended spelling on a piece of paper. Note that if your group uses the honor system and you intended on betraying that trust with dishonorable play, be sure and balance the number of "correct" and "incorrect" guesses, or your credibility may come into question.
Verboten
A player may not ask for the spelling of a prior word or the last letter of a word. Players must infer the spelling from the spoken word, its definition, or clarifying sentence. If the player does not know the spelling of the word, that player must guess.
Players may not consult a dictionary or other printed material except to resolve a challenge. Environmental materials, e.g. road signs, may be consulted, but this is—as you can imagine—an unreliable strategy.

Options

Markers - Games played within large group with good vocabulary and strong spelling skills can take hours, during which it can be troublesome to remember who had how many points. The use of physical tokens representing the number of lives remaining per player can alleviate the memory burden. In our last game we used Pepperidge Farm Flavor Blasted Goldfish™ as markers for the remaining number of lives, with the added consolation that if you lost a life, you still get a tasty treat.
Documentation - Long games, multiple trains, and word variations can tax players trying to remember if a word has already been used in the current train. For this reason, appointing someone to document the trains can come in quite handy. This person will have an unfair advantage in knowing what words have been already spoken in the current train, so it's a good idea to have this person not be a player in the current game. One idea is to appoint the winner of the last game as the documentarian for the current game, as this helps balance the odds for less skilled players across multiple games. The documentarian will need to be careful and not ask for clarifications of homophones or spelling variations, as the homophone-speaking player may be relying on the ambiguity as part of their strategy. The documentarian should wait until the responding player has spoken their word before asking for clarifications.
Word Forms - Spelling variances on the same meaning of a word, such as plurals, gerunds, and adverbs are a matter of preference. If you have no documentarian, you may wish to disallow variations to ease the burden on memory.
Optional caboosing - We play that following a word ending in "c," the response "caboose" is required. Making it a perogative of the responding player inserts personal politics into the game. If you dig that, permit it.
Challenges - More competitive groups may wish to formalize challenges. In this type of play, all words are accepted unless challenged by another player. If the challenger is correct and the word is unacceptable, the challenged player loses a life. If the challenger is incorrect and the word is acceptable, the challenger loses a life. For example, if a player said "bob" and was challenged because another player notes it is a proper noun, the first player can remind the other that "bob" is also a verb, and the challenger would lose a life. I like this type of play, but not everyone does.
Definitions - To avoid fake words in the absence of a dictionary, players may challenge others to define unusual or unfamiliar words. If the challenged player cannot define their word to the satisfaction of the other players, they lose a life. Note that this can result in bitterness on the part of the challenged if they have a vast vocabulary but poor debate skills, or foolishness on the part of the challenger if the player has a crappy vocabulary but excellent balderdash skills.
No Extra Engines - Players interested in a greater challenge can adhere more closely to the train metaphor and disallow words that end in the letter "e," since the following word could be "engine," which should only be at the beginning of a train. Since e is the most common word ending in English, this restriction is significant.

Strategies

If you play the game a while you'll notice some familiar strategies popping up. Some are offensive, forcing the player following you into a linguistic corner. Some are defensive, which help you overcome the odd vocabulary freeze that occurs about 30 minutes into the game, where you know that there must be thousands of words beginning with your target letter, but you can only think of the ones that have already been used.

Homophones - This is the crappiest strategy. It relies on either the ignorance or the distraction of the player following you. And often, it only works once. If you overuse it, your mark will ask for a definition or example sentence for every play. On the other hand, it can be a personal challenge to realize a homophone for every letter passed your way, in which case you may simply provide the definition after the word.
Foreign-rooted words - This is the second crappiest strategy, as it also relies on the ignorance of the player following you. On the other hand, it can lead the game in interesting directions since foreign-rooted words can have endings quite uncommon to English, such as "orzo."
Scrabblese- The Scrabble™ dictionary is famous for listing obscure words that obsessive players are prone to memorize, e.g. "mezquit." The further players reach into obscurity, however, the more of an imperfect-information game it becomes, and the less fun for "normal" people. Nonetheless, if you know the meaning of the words (the Scrabble dictionary does not provide definitions) or have an unabridged dictionary on hand to confirm such words, this is technically permissable.
Trains of thought - A defensive strategy that helps you break out of vocabulary freeze is to try and find words that not only chain to the prior word by letter, but share some association. For example, if the prior word is "slick", you might try to find a word that not only begins with a "k," but that is also slick, such as a "kayak" which can be called "slick" when it is wet. Trains of thought may also arise naturally during the course of a game often to the delight of its players.
Letter hounding - This is the most common strategy, often evolving naturally as the structure of English tends towards certain endings. In it, players try to find words that end in a particular and particularly vexing letter, such as k, y, and o. The letter "y" is a particularly easy target if your game permits adverbs. Note that if everyone in a game with an even number of players uses this strategy, the "bad" turns stay with the same people every round. If a game has an odd number of players, the "bad" turn alternates between players each round. This pattern of play can be confounded by the use of letter-*-letter words that begin and end with the same letter. This can turn the tide in a two player game, and so it is useful to familiarize yourself with a few of these words in the difficult letter categories.

Variation: Dialogue Caboose

I made up this variation quite recently while playing Caboose with my nephew, and we both enjoyed the result. After inventing it, I discovered this is similar to an improvisation game called Last Letter, First Letter. In Dialogue Caboose, you couch the word in a sentence in which no other words begin with the target letter. This helps clarify the meaning from the start, but requires a little more parsing and thinking per turn. It follows that we had to include a new rule, that if you accidentally include another word with the target beginning letter, you lose a life. An example follows.

"Can you help me? It seems my engine won't start."
"Sure. Have you ever started it before?"
"Really, what kind of question is that?"
"I'm just checking, you never know."
"That's an understatement..."

Etc. Note that the bold is only for this writeup. We don't actually stress thre word since part of the fun is finding the keyword. The rest of the fun is the crazy dialogue that results, and the fact that you can carry it out in stores, on elevators, and people just think you're crazy.

Anyway, that's Caboose. I hope it's a handy game for you and yours on your next long journey.

Appendices

This has been placed at the end so that if you would like to print these rules and take them with you, you can tear off these lists, which are kind of cheat sheets (read: study aids).

Note that neither of these lists are exhaustive.

Uncommon Homophones

Specifically where one of the pair is common and the other of the pair is obscure, the words have similar beginning letters, different ending letters, and neither end nor begin with c.

Format: Common, Uncommon - (One) Definition of the uncomon word (Since you will be asked)

away, aweigh - raised just clear of the bottom -- used of an anchor.
axle, axel - a jump in figure skating from the outer forward edge of one skate with 1 1/2 turns taken in the air and a return to the outer backward edge of the other skate.
bait, bate - to reduce the force or intensity of, similar to abate.
bays, baize - a coarse woolen or cotton fabric napped to imitate felt.
bow, beau - boyfriend.
bite (or byte), bight - a bend in a coast forming an open bay.
bray, brae - a hillside especially along a river. (chiefly Scottish, Americans may have a hard time selling this.)
buyer, byre - a cow barn.
flow, floe - floating ice formed in a large sheet on the surface of a body of water.
furs, furze - a spiny yellow-flowered European shrub of the legume family.
jewel, joule - unit of work or energy equal to the work done by a force of onenewton acting through a distance of one meter.
laid, lade - to put a load or burden on or in. (Think of "ladle.")
lamb, lam - to flee hastily.
lee, lea - arable land used temporarily for hay or grazing. (Often "ley", may be a tough sell.)
loop, loupe - a small magnifier used especially by jewelers, watchmakers, and printers.
pie, pi - the symbol π denoting the ratio of the circumference of a circle to its diameter.
review, revue - a theatrical production consisting typically of brief loosely connected often satirical skits, songs, and dances.
row, roe - the adult female of various mammals (as a deer, rabbit, or kangaroo) of which the male is called buck.
rude, rood - a large crucifix on a beam or screen at the entrance to the chancel of a church.
tear, tare - a weed of grainfields.

Letter-*-Letter Words

These are useful for turning the tide on a Letter Hounding strategy as mentioned above. According to the International House of Logorrhea, the ten least common starting letters are, in order of infrequency, y, x, q, j, z, u, k, w, n, v. The ten most common ending letters are, in order, e, s, y, n, t, m, r, a, c, l. These overlap strongly with y and less strongly with n, so I've included these. In my experience, G, K, and O have also been a problem. And although I can't find any statistical reason why this is, I've included some useful words for these letters as well.

G

(specifically a problem when variants such as gerunds and infinitives are disallowed)

gag
gelding
gong
gosling
grog
groundhog
gulag

K

kayak
kick
kickback
kinfolk
kiosk
knack
knock

N

napkin
narration
nation
neaten
negation
neocon
neon
neurotoxin
neutron
newborn
newsman
nightgown
nineteen
nitrogen
nobleman
noblewoman
noggin
noon
northern
noun
nutrition
nylon

O

obligato
onto
oratorio
orzo
outdo

Y

yay
yearly
yeasty
yeomanry
yesterday
yucky
yummy
(Once my friend C tried to foist "yesteryearly" off on us, and argument raged for quite a while. She eventually lost for lack of a sensible example, so I'd advise against it.)

_{Sources for the
Appendices:
International House of Logorrhea
http://phrontistery.50megs.com/ihlstart.html}

_{Mirriam-Webster
http://www.m-w.com}

English words that end with V	railway cars	Disneyland Railroad	rolling stock
Travel changes your brain	Titusville, Pennsylvania	Ring the cactus, buy the house a round	Chaetopoda
Last Letter, First Letter	Lehmann-Gross-Bahn	Coboose	skinny dipping
Scooby Snacks	Boggle	Red vs. Blue	Heinie Manush
Kinzua Viaduct	CafePress	Sugar Ray	Pulk/Pull Revolving Doors
Tom T. Hall

Caboose (thing)