| 100% | LAMANCHA | 8 | Man of __, 1960s musical about Don Quixote |
| 65% | MANCHA | 6 | Man of La __, Don Quixote musical |
| 65% | LAMANCHA | 8 | Don Quixote-inspired musical: Man of __ |
| 61% | MANOFLAMANCHA | 13 | Musical about Don Quixote |
| 42% | HAIR | 4 | Musical about 1960s counterculture |
| 41% | GODSPELL | 8 | Musical about the Gospel of Matthew |
| 41% | MORMON | 6 | Musical about missionaries, The Book of __ |
| 39% | ROCINANTE | 9 | Don Quixote's horse; anagram of It ran once |
| 39% | PHANTOM | 7 | Musical about a Leroux book: The __ of the Opera |
| 39% | PIPPIN | 6 | Broadway musical about the son of Charlemagne |
| 39% | WICKED | 6 | Broadway musical about the witches of Oz |
| 38% | CHAIR | 5 | About musical piece of furniture |
| 38% | DRAPER | 6 | Don __ protagonist of Mad Men |
| 38% | HAIRSPRAY | 9 | Musical about a girl who dreams of dancing on TV |
| 38% | SIX | 3 | Broadway musical about the wives of Henry VIII |
| 38% | DIANA | 5 | 2019 musical about a former Princess of Wales |
| 37% | CHER | 4 | "The ___ Show" (Broadway musical about the singer of "Believe") |
| 37% | IFTHEN | 6 | Idina Menzel musical about the consequences of our choices |
| 37% | PORGYANDBISQUE | 14 | Musical drama about a man eating soup? |
| 37% | GILLIGANSISLAND | 15 | 1960s sitcom about a group of castaways |
| 36% | PETE | 4 | Colleague of Don on "Mad Men" |
| 36% | SPAIN | 5 | Home of Don Quixote |
| 36% | COMEFROMAWAY | 12 | Post-9/11 musical about the diversion of flights to Newfoundland |
| 35% | PETE | 4 | Officemate of Don and Peggy on "Mad Men" |
| 34% | FUNNYGIRL | 9 | 1964 Broadway musical about the life and career of 21-Across: 2 wds. |
| 34% | ALOT | 4 | "___ of people don't know this about me": 2 wds. |
| 34% | HAIR | 4 | "Easy to Be Hard" musical of the late 1960s |
| 34% | AGENCY | 6 | Mad Men is about this kind of advertising business |
| 34% | THEPASSION | 10 | Fox live musical about the final hours of the life of Jesus: 2 wds. |
| 34% | AINTTOOPROUD | 12 | Tony-nominated jukebox musical about the life and times of 34-Across: 3 wds. |