| 100% | PETE | 4 | Colleague of Don on "Mad Men" |
| 64% | PETE | 4 | Officemate of Don and Peggy on "Mad Men" |
| 56% | DRAPER | 6 | Don __ protagonist of Mad Men |
| 52% | DRAPER | 6 | Don or Betty on "Mad Men" |
| 47% | NORADUNN | 8 | Colleague of Dana Carvey on "S.N.L." |
| 47% | OLD | 3 | ___ Fashioned, popular cocktail which is also the signature drink of Don Draper in "Mad Men" |
| 47% | AGENCY | 6 | Mad Men is about this kind of advertising business |
| 47% | ELENA | 5 | Colleague of Ruth and Sonia on the Supreme Court |
| 47% | DONNA | 5 | Colleague of Leslie and Tom on "Parks and Recreation" |
| 46% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 46% | JONHAMM | 7 | Don Draper's portrayer on "Mad Men": 2 wds. |
| 46% | TED | 3 | Colleague of Keeley and Rebecca, on an Apple TV+ show |
| 46% | JONHAMM | 7 | He played the 60s Mad Man Don Draper |
| 45% | BLOKE | 5 | Man, on the Isle of Man |
| 45% | MANCHA | 6 | Man of La __, Don Quixote musical |
| 45% | LAMANCHA | 8 | Don Quixote-inspired musical: Man of __ |
| 45% | MADISON | 7 | Mad Men was named after ad men on this NY avenue |
| 45% | LAMANCHA | 8 | Man of __, 1960s musical about Don Quixote |
| 44% | TED | 3 | Colleague of Mary, Murray and Lou on "The Mary Tyler Moore Show" |
| 43% | CLIO | 4 | Award won by Don Draper on "Mad Men" |
| 43% | PRESIDENTS | 10 | Many of the men appearing on money |
| 43% | SNAEFELL | 8 | Highest mountain on the Isle of Man |
| 42% | ERIN | 4 | Port ___, seaside resort on the Isle of Man |
| 42% | BEARD | 5 | Growth of hair on a man's face |
| 42% | NED | 3 | ___ Stark, man from Winterfell on "Game of Thrones" |
| 42% | BEARD | 5 | Growth of hair on a man’s face |
| 42% | BEATRIZ | 7 | Actress Stephanie of "A Man on the Inside" |
| 42% | TED | 3 | Actor ___ Danson of "A Man on the Inside" |
| 41% | ALDRIN | 6 | One of the first men on the moon, Buzz |
| 41% | TEN | 3 | Number of players on a men's lacrosse team |