| Most shabby | 11 |
| Most sexually alluring | 22 |
| Most severe, or least severe | 28 |
| Most severe | 11 |
| Most serious, as a felony | 25 |
| Most serious or least serious | 29 |
| Most serious | 12 |
| Most serene | 11 |
| Most sentimental | 16 |
| Most sensitive | 14 |
| Most sensible and staid | 23 |
| Most sensible | 13 |
| Most senseless | 14 |
| Most senior, say | 16 |
| Most senior | 11 |
| Most senators | 13 |
| Most self-satisfied | 19 |
| Most self-affirmingly gay | 25 |
| Most seldom seen | 16 |
| Most see-through | 16 |
| Most secure | 11 |
| Most secluded | 13 |
| Most Scroogelike | 16 |
| Most scoutmasters | 17 |
| Most scorching | 14 |
| Most scary | 10 |
| Most scarce | 11 |
| Most scanty | 11 |
| Most scant | 10 |
| Most savory | 11 |
| Most Saudis and Iraqis | 22 |
| Most saucy | 10 |
| Most satyric | 12 |
| Most satisfactory | 17 |
| Most sardonic | 13 |
| Most sarcastic, as remarks | 26 |
| Most sapient | 12 |
| Most sanitary | 13 |
| Most sallow | 11 |
| Most saintly | 12 |
| Most sage | 9 |
| Most sagacious | 14 |
| Most safe | 9 |
| Most sad | 8 |
| Most sacred building in Islam | 29 |
| Most sacred | 11 |
| Most saccharine | 15 |
| Most runtlike | 13 |
| Most rundown | 12 |
| Most rueful | 11 |
| Most rubicund | 13 |
| Most rough-sounding | 19 |
| Most rough, at sea | 18 |
| Most rough, as cliffs | 21 |
| Most robust | 11 |
| Most roadsters | 14 |
| Most ritzy | 10 |
| Most risqué | 14 |
| Most Ripleyesque | 16 |
| Most rigid | 10 |
| Most revolting | 14 |
| Most revered person in the land, in Boston? | 43 |
| Most revered | 12 |
| Most retirees: Abbr. | 20 |
| Most ret. people | 16 |
| Most restricted, filmwise | 25 |
| Most restless | 13 |
| Most respectful (of) | 20 |
| Most respected, perhaps | 23 |
| Most resourceful | 16 |
| Most reserved | 13 |
| Most resentful | 14 |
| Most repulsive | 14 |
| Most reprehensible, as motives | 30 |
| Most reprehensible | 18 |
| Most repellent | 14 |
| Most remote | 11 |
| Most religiously homogeneous state in America | 45 |
| Most reliable | 13 |
| Most relaxed | 12 |
| Most refined and sophisticated | 30 |
| Most refined | 12 |
| Most red, maybe | 15 |
| Most red | 8 |
| Most reckless | 13 |
| Most recently produced | 22 |
| Most recently out of rompers | 28 |
| Most recently introduced | 24 |
| Most recently from | 18 |
| Most recently | 13 |
| Most recent player to win MVP, All-Star Game MVP, and Finals MVP in one season | 78 |
| Most recent news | 16 |
| Most recent music | 17 |
| Most recent glacial period | 26 |
| Most recent box office arrival, probably | 40 |
| Most recent 600-homer club member | 33 |
| Most recent | 11 |
| Most reasonable | 15 |
| Most real | 9 |
| Most ready for plucking | 23 |