| Least hampered | 14 |
| Least happy | 11 |
| Least happy, in Vegas | 21 |
| Least harsh | 11 |
| Least hasty | 11 |
| Least hazy | 10 |
| Least healthy | 13 |
| Least healthy-looking | 21 |
| Least heavy | 11 |
| Least helpful, as a description | 31 |
| Least homely | 12 |
| Least honorable | 15 |
| Least hopeful | 13 |
| Least hospitable | 16 |
| Least idea | 10 |
| Least iffy | 10 |
| Least important | 15 |
| Least imposing | 14 |
| Least impressive place of business? | 35 |
| Least in need of a cleanup | 26 |
| Least inane | 11 |
| Least inclined to do anything | 29 |
| Least incompetent | 17 |
| Least infirm | 12 |
| Least ingenuous | 15 |
| Least inhibited | 15 |
| Least inspiring | 15 |
| Least intelligent | 17 |
| Least intense | 13 |
| Least interesting | 17 |
| Least interesting travel hub? | 29 |
| Least involved | 14 |
| Least irrigated | 15 |
| Least joyful | 12 |
| Least klutzy | 12 |
| Least known | 11 |
| Least large | 11 |
| Least laugh-out-loud, as humor | 30 |
| Least lavish | 12 |
| Least legitimate | 16 |
| Least lenient | 13 |
| Least like Emily Post | 21 |
| Least likely | 12 |
| Least likely to attack | 22 |
| Least likely to be found | 24 |
| Least likely to be free | 23 |
| Least likely to be located | 26 |
| Least likely to be missed | 25 |
| Least likely to be pinned down | 30 |
| Least likely to be spotted | 26 |
| Least likely to bend | 20 |
| Least likely to betray | 22 |
| Least likely to bite | 20 |
| Least likely to crack | 21 |
| Least likely to earn a G rating | 31 |
| Least likely to forgive | 23 |
| Least likely to get it | 22 |
| Least likely to last | 20 |
| Least likely to let you sleep | 29 |
| Least likely to lose it | 23 |
| Least likely to make a faux pas | 31 |
| Least likely to make the NBA | 28 |
| Least likely to rain | 20 |
| Least likely to snap? | 21 |
| Least likely to speak up | 24 |
| Least likely to take command | 28 |
| Least likely to tip | 19 |
| Least likely to turn tail | 25 |
| Least likely to understand | 26 |
| Least likely to win a Tony, perhaps | 35 |
| Least likely to work | 20 |
| Least lit | 9 |
| Least littered | 14 |
| Least little bit | 16 |
| Least loco | 10 |
| Least long | 10 |
| Least longwinded | 16 |
| Least loony | 11 |
| Least loopy | 11 |
| Least loose | 11 |
| Least lovely | 12 |
| Least loyal | 11 |
| Least lucid | 11 |
| Least lumbering | 15 |
| Least lunatic | 13 |
| Least mad | 9 |
| Least magnanimous | 17 |
| Least malleable | 15 |
| Least mannerly | 14 |
| Least mean | 10 |
| Least meaningful | 16 |
| Least menacing | 14 |
| Least mental | 12 |
| Least merry | 11 |
| Least messy | 11 |
| Least minuscule | 15 |
| Least modest | 12 |
| Least moist | 11 |
| Least moneyed | 13 |
| Least moral | 11 |