| 100% | BOTTLENECK | 10 | (A Napa wine guy and a NAPA auto-parts guy meet at a party, and the wine guy immediately starts with the jokes) ... "How ya doin'! Say, I woulda been here sooner but I hit a ___!" |
| 26% | OLDMAN | 6 | Neil Young hit with the lyrics “Look at my life / I’m a lot like you were” |
| 26% | CARDIGAN | 8 | Hit single from 15-Across with the lyrics "You put me on and said I was your favorite" |
| 26% | CARDIGAN | 8 | Taylor Swift hit with the lyric "You put me on and said I was your favorite" |
| 25% | CARDIGAN | 8 | Taylor Swift hit with the lyric "You put me on and said I was your favorite" |
| 25% | IMAMAN | 6 | 1967 hit with the repeated lyric "Yes I am / And I can't help / But love you so" |
| 25% | MARGARITAVILLE | 14 | 42-Across hit song with the lyrics "But there's booze in the blender / And soon it will render / That frozen concoction that helps me hang on" |
| 25% | SIMONE | 6 | I was a part of the "Final Five" at the 2016 Olympics and won four gold medals |
| 24% | BARBIEWORLD | 11 | 2023 Nicki Minaj and Ice Spice hit with the lyric "I'm a doll but I still wanna party": 2 wds. |
| 24% | FASTCAR | 7 | Tracy Chapman hit with the line "I had a feeling I could be someone" (1988) |
| 24% | LIKEAPRAYER | 11 | Madonna hit that starts with the lyric "Life is a mystery" |
| 24% | WEAREFAMILY | 11 | Sister Sledge classic whose second line is "I got all my sisters with me," and a hint to the starts of 17-, 24-, 39-, and 49-Across |
| 23% | LSD | 3 | Drug that sangria at a party is laced with, in the movie Climax |
| 23% | IBELIEVEICANFLY | 15 | R. Kelly hit whose last title word is aptly rhymed with "sky" in the lyrics ... and a hint to the starts of the other four longest puzzle answers |
| 23% | THELOVEILOST | 12 | 1973 hit single by 44-Across and 30-Across with the lyrics "Take a good look at me / I'm in misery, can't you see?" (4 wds.) |
| 23% | PINK | 4 | Singer with the hits "Get the Party Started" and "So What" |
| 23% | ITOO | 4 | Langston Hughes poem with the lines "They'll see how beautiful I am / And be ashamed" |
| 23% | ITOO | 4 | Langston Hughes poem with the lines "They'll see how beautiful I am / and be ashamed-" |
| 23% | NEIL | 4 | With 15-Across, "How I Met Your Mother" actor who won a 2014 Tony Award for starring in "Hedwig and the Angry Inch" |
| 22% | IMAGINE | 7 | 1971 hit with the lyric "You may say I'm a dreamer" |
| 22% | TONGUETIED | 10 | At a loss for words, and what the starts of 17-, 23-, 38- and 47-Across can literally be? |
| 22% | SUPERTROUPER | 12 | ABBA hit with the lyric "All I do is eat and sleep and sing" |
| 22% | PUN | 3 | Joke with a homophone, say, that is the so-called "lowest form of humor" |
| 22% | TONI | 4 | Singer Watson, a.k.a. Tones and I, with the 2019 hit "Dance Monkey" |
| 22% | NAT | 3 | I played jazz and was a part of the King Cole Trio |
| 22% | ITOOSINGAMERICA | 15 | Opening of the Langston Hughes poem with the lines "They'll see how beautiful I am / And be ashamed" |
| 22% | GIMMEABREAK | 11 | "You gotta be joking!" and a hint to the last parts of 21-, 31- and 42-Across |
| 22% | ITSGROWINGONME | 14 | "I wasn't sure at first, but ...," or what could be said about the ends of 16-, 26-, and 44-Across? |
| 22% | STILLDRE | 8 | 1999 hit with the lyrics “They say rap’s changed / They wanna know how I feel about it” |
| 22% | SOTOMAYOR | 9 | Supreme Court justice who once said "I am a New Yorker, and 7 a.m. is a civilized hour to finish the day, not to start it" |