| ___ Book (old English record) | 29 |
| ___ Book Club | 13 |
| ___ Booker (Rhodes Scholar, Yale Law graduate, and New Jersey's first African-American US senator) | 102 |
| ___ Books (paperback publisher) | 31 |
| ___ boom | 8 |
| ___ boom (attack) | 17 |
| ___ boom bah | 12 |
| ___ boomers (Generation Y) | 26 |
| ___ boost | 9 |
| ___ Booth Luce | 14 |
| ___ Boothe Luce | 15 |
| ___ boots ('60s footwear) | 29 |
| ___ boots (knee-high '60s fashion) | 38 |
| ___ boots (knee-high style) | 27 |
| ___ boots: '60s fashion | 27 |
| ___ Bora | 8 |
| ___ Bora (Afghan mountain area) | 31 |
| ___ Bora (Afghan region) | 24 |
| ___ Bora (Afghanistan locale) | 29 |
| ___ Bora (former Taliban stronghold) | 36 |
| ___ Bora (mountain area in old bin Laden news) | 46 |
| ___ Bora caves | 14 |
| ___ Bora, Afghan region | 23 |
| ___ Bora, wild part of Afghanistan | 34 |
| ___ Borch, Dutch artist | 23 |
| ___ Borch, Dutch painter | 24 |
| ___ borealis | 12 |
| ___ borealis (northern lights) | 30 |
| ___ boredom | 11 |
| ___ boredom (be completely turned off) | 38 |
| ___ Bornes | 10 |
| ___ Bornes (card game) | 22 |
| ___ Bornes (classic card game) | 30 |
| ___ Bornes (French card game) | 29 |
| ___ Bornes (game) | 17 |
| ___ Boru, Irish king who defeated the Norse | 43 |
| ___ bosom (heaven) | 18 |
| ___ Boss | 8 |
| ___ boss (casino employee) | 26 |
| ___ bottle glasses | 18 |
| ___ bottom | 10 |
| ___ Bottom, Titania's dreamboat | 35 |
| ___ bouche (delicacy) | 21 |
| ___ bouche (tidbit) | 19 |
| ___ bouffe | 10 |
| ___ bounds (very fast) | 22 |
| ___ Bountiful | 13 |
| ___ Bounty | 10 |
| ___ bourgeois | 13 |
| ___ bourgeoisie (gentry) | 24 |
| ___ bourguignon | 15 |
| ___ Bourguignonne | 17 |
| ___ bourrée (ballet move) | 28 |
| ___ Bovary | 10 |
| ___ Bow, river in Wyo. | 22 |
| ___ bower (spare anchor) | 24 |
| ___ Bowl | 8 |
| ___ Bowl (annual college football game between the Big Ten and the Big 12) | 74 |
| ___ Bowl (former sporting event) | 32 |
| ___ Bowl (game a week after Super Sunday) | 41 |
| ___ Bowl (postseason game) | 26 |
| ___ Bowl, for all-pro teams | 27 |
| ___ box | 7 |
| ___ box (carpentry device) | 26 |
| ___ box (computer screen pop-up) | 32 |
| ___ box (TV) | 12 |
| ___ box of Greek myth | 21 |
| ___ boy | 7 |
| ___ boy (apron-strings gripper) | 31 |
| ___ Boy (dog food brand) | 24 |
| ___ boy (hero sandwich) | 23 |
| ___ boy (Mel Ott) | 17 |
| ___ boy (sissy) | 15 |
| ___ boy (spoiled lad) | 21 |
| ___ boy (timid man) | 19 |
| ___ boy (wuss) | 14 |
| ___ boy! | 8 |
| ___ Boy, classic figure in Japanese anime | 41 |
| ___ Boy, Harding's Airedale | 31 |
| ___ boys (good guy) | 19 |
| ___ Boys' Choir | 19 |
| ___ brace (device used to immobilize the head and neck) | 55 |
| ___ bracelet | 12 |
| ___ Bradley handbags | 20 |
| ___ Bradshaw, "Sex and the City" role | 47 |
| ___ Bradstreet, America's first published poet | 50 |
| ___ Braga, Brazilian film star | 30 |
| ___ brain (nitwit) | 18 |
| ___ Brainard, the Absent-Minded Professor | 41 |
| ___ Braithwaite ("Downton Abbey" character) | 53 |
| ___ bran | 8 |
| ___ bran muffins | 16 |
| ___ branch | 10 |
| ___ branch (entirely) | 21 |
| ___ branch (peace emblem) | 25 |
| ___ branch (peace offering) | 27 |
| ___ branch (utterly) | 20 |
| ___ Branco | 10 |
| ___ Branco, Brazil | 18 |
| ___ brand | 9 |