| 100% | FED | 3 | "I'm ___ up with him!" |
| 69% | BORED | 5 | "break up with your girlfriend, i'm ___" (Ariana Grande song) |
| 68% | ARI | 3 | "Break Up With Your Girlfriend, I'm Bored" artist, to fans |
| 67% | ARI | 3 | "Break Up With Your Girlfriend, I'm Bored" singer Grande's nickname |
| 63% | CAMETONOTHING | 13 | "Then my friend set me up with a recluse, but he ..." |
| 60% | JACK | 4 | He climbed up the hill with Jill |
| 60% | INEEDA | 6 | With 78-Down, "Please cheer me up" |
| 59% | SHEESH | 6 | "The things I put up with!" |
| 58% | SILVERM | 7 | With 62-Across, Runner-up (who cracks ME up!) |
| 58% | HERMANM | 7 | With 40-Across, American novelist (who cracks ME up!) |
| 57% | LIT | 3 | "The kid's eyes ___ up with joy when he saw the gifts." |
| 57% | LIT | 3 | "The kid's eyes ___ up with joy when he saw the gifts" |
| 57% | EASYCOM | 7 | With 18-Across, Spendthrift's motto (which cracks ME up!) |
| 57% | JANEEYRE | 8 | Novel with the line "Reader, I married him" |
| 57% | EINSTEIN | 8 | He came up with the equation "E = mc²" |
| 55% | DEVIL | 5 | He "made me do it," with "the" [4] |
| 55% | CORN | 4 | Fall staple that would butter you up with "I'm all ears for you!" |
| 54% | AVICII | 6 | Swedish DJ and producer, had hit with Wake Me Up |
| 54% | YOURLUVIN | 9 | Give Me All __, with Madonna, Nicki Minaj, M.I.A. |
| 54% | JACK | 4 | ___ o'lantern, fall staple that would butter you up with "You make me light up!" |
| 54% | OUTA | 4 | "I'm sure they'll figure ___ way" ("They'll come up with a plan!"): 2 wds. |
| 54% | PROM | 4 | High school dance where Lily broke up with Scooter on "How I Met Your Mother" |
| 53% | AVICII | 6 | Late Swedish electronic musician with the 2013 hit "Wake Me Up" |
| 53% | MELODIC | 7 | I'm cold, working with English musical |
| 53% | CAT | 3 | I'm a mammal with "nine lives" |
| 53% | PEI | 3 | I.M. with a Pritzker Prize |
| 52% | LMAO | 4 | "OMG, I'm cracking up!" |
| 52% | GOTIT | 5 | "Now I'm with you" |
| 52% | BADD | 4 | Color Me ___, group with the 1991 hit "I Wanna Sex You Up" |
| 52% | WHAM | 4 | Duo with the 1984 hit "Wake Me Up Before You Go-Go" |