| 100% | ARIANA | 6 | Pop queen with the 2019 single "Break Up With Your Girlfriend, I'm Bored" |
| 55% | ARI | 3 | "Break Up With Your Girlfriend, I'm Bored" artist, to fans |
| 54% | ARI | 3 | "Break Up With Your Girlfriend, I'm Bored" singer Grande's nickname |
| 37% | PETERFRAMPTON | 13 | "I'm in You" singer with the hit single "Baby, I Love Your Way": 2 wds. |
| 36% | HANNAHBROWN | 11 | "The Bachelorette" 2019 lead, who broke up with Jed Wyatt after discovering he had a girlfriend during filming: 2 wds. |
| 36% | LEANONME | 8 | 1972 #1 hit with the lyric "I'm right up the road / I'll share your load" |
| 35% | NIGHTMARE | 9 | 2019 Top 20 single by Halsey with the lyric "I'm no sweet dream" |
| 34% | PROM | 4 | High school dance where Lily broke up with Scooter on "How I Met Your Mother" |
| 33% | ABBA | 4 | Band with the singles “Knowing Me, Knowing You” and “Does Your Mother Know” |
| 33% | BARNEYSTINSON | 13 | "How I Met Your Mother" character with the catchphrase "Suit up!": 2 wds. |
| 33% | CARDIGAN | 8 | Hit single from 15-Across with the lyrics "You put me on and said I was your favorite" |
| 32% | CHER | 4 | Pop star with the 2019 "Here We Go Again" tour |
| 31% | ROYALS | 6 | 2013 Lorde hit song with the lyrics "Let me be your ruler, you can call me Queen B" |
| 31% | ROYALS | 6 | 2013 Lorde hit song with the lyric "Let me be your ruler, you can call me queen bee" |
| 31% | TORN | 4 | He was ___ with grief after break up with his girlfriend |
| 31% | DMX | 3 | Rapper with the 2000 single "Party Up (Up in Here)" |
| 30% | HALO | 4 | Beyoncé hit with the line "Think I'm addicted to your light" |
| 30% | NSYNC | 5 | Pop group with the No. 1 hit "It's Gonna Be Me" |
| 30% | VACUUM | 6 | I suck up dust and debris with ease. I am the one-stop shop for your dusting needs. Who am I? |
| 30% | AHA | 3 | Pop band with the 1985 hit "Take on Me": Hyph. |
| 30% | AHA | 3 | Pop group with the 1985 hit "Take On Me": Hyph. |
| 30% | MOON | 4 | With 6-Across, classic song with the lyric "Wherever you're goin', I'm goin' your way" |
| 30% | CHERRYBOMB | 10 | 1976 song by the Runaways with the lyric "Hello world, I'm your wild girl" |
| 30% | BALL | 4 | "Wrecking ___" (Miley Cyrus hit with the lyrics "I never hit so hard in love / All I wanted was to break your walls") |
| 29% | SUBLIME | 7 | Rock trio with the 1996 single "What I Got" |
| 29% | MRAZ | 4 | Jason with the 2008 hit song "I'm Yours" |
| 29% | BEJEWELED | 9 | Top 10 single from 37-Across with the lyrics "Diamonds in my eyes / I polish up ... real nice / ... / Sapphire tears on my face" |
| 29% | HALSEY | 6 | One-named singer with the 2019 #1 hit "Without Me" |
| 29% | LETYOUBERIGHT | 13 | Hit single by 9-Down with the lyric "We can make up if you just kiss me at the next traffic light" (4 wds.) |
| 29% | ABBA | 4 | Swedish pop group with the hits 11-Down and "Dancing Queen" |