| 100% | JON | 3 | With 45-Down, Don Draper portrayer on "Mad Men" |
| 60% | JONHAMM | 7 | Don Draper's portrayer on "Mad Men": 2 wds. |
| 57% | JONHAMM | 7 | Don Draper portrayer in “Mad Men” |
| 48% | ROSEN | 5 | Arnie __, Don Draper's neighbor on "Mad Men" |
| 48% | CLIO | 4 | Award won by Don Draper on "Mad Men" |
| 47% | HAMM | 4 | Jon ___, actor who plays the protagonist Don Draper on the TV series "Mad Men" |
| 45% | JONHAMM | 7 | He played the 60s Mad Man Don Draper |
| 43% | JONHAMM | 7 | Actor who played Don Draper in US television drama series Mad Men |
| 42% | HAMM | 4 | Jon —, actor who played Don Draper in US television drama series Mad Men |
| 42% | HANDSOFFTHE | 11 | With 45-Across, "I don't need two silly sticks that rotate on my timepiece!" |
| 41% | DRAPER | 6 | Don or Betty on "Mad Men" |
| 40% | OLD | 3 | "___ Fashioned," Don Draper's signature cocktail in "Mad Men" |
| 39% | DOUBLE | 6 | With 45 Down, alternate puzzle title |
| 39% | SCALE | 5 | With 45 Down, architect's creation |
| 39% | PET | 3 | With 45 Down, watches Spot, say |
| 39% | LOS | 3 | With 45 Down, Silicon Valley city |
| 39% | MAD | 3 | "___ Men" (series with Don Draper) |
| 39% | PET | 3 | With 45 Down, hardly a personal preference |
| 38% | MAD | 3 | Don Draper's "___ Men" |
| 37% | COOPER | 6 | Sterling ___ & Partners, advertising agency where Don Draper of "Mad Men" works |
| 36% | PETE | 4 | Officemate of Don and Peggy on "Mad Men" |
| 36% | PETE | 4 | Colleague of Don on "Mad Men" |
| 36% | UPTO | 4 | With 45-Across, informed on the latest |
| 35% | TAKE | 4 | With 45-Across, focus directly on hitting someone |
| 35% | OLD | 3 | ___ Fashioned, popular cocktail which is also the signature drink of Don Draper in "Mad Men" |
| 35% | IMISSYOU | 8 | Song on the 50-Across album "25" with the line "Baby, don't let the lights go down" (3 wds.) |
| 35% | ADMAN | 5 | Don Draper or Roger Sterling, on an AMC series |
| 35% | EDONEILL | 8 | Al Bundy portrayer on "Married ... With Children" |
| 34% | OUTS | 4 | On the __ with; mad at |
| 34% | ADMEN | 5 | Don Draper and Roger Sterling on a hit AMC series |