| 100% | PAULMCCARTNEY | 13 | Singer who performed "Maybe I'm Amazed" on the SNL40 anniversary special: 2 wds. |
| 64% | PAULSIMON | 9 | Singer who performed "Still Crazy After All These Years" on the SNL40 anniversary special: 2 wds. |
| 61% | KANYEWEST | 9 | Rapper who performed "Jesus Walks" on the SNL40 anniversary special: 2 wds. |
| 48% | FIONAAPPLE | 10 | Grammy-winning singer who performs the theme song "Container" on "The Affair": 2 wds. |
| 48% | MILEYCYRUS | 10 | "Wrecking Ball" singer who performs on the remix of 49-Across: 2 wds. |
| 46% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 45% | QUEENLATIFAH | 12 | Singer who performed "That's the Letter O" (a parody of "That's the Way We Flow") on "Sesame Street": 2 wds. |
| 44% | JOHNLEGEND | 10 | "All of Me" singer who performed "History Has Its Eyes on You" on "The Hamilton Mixtape": 2 wds. |
| 43% | BEBEREXHA | 9 | Singer who performed on 15-, 27-, and 34-Across: 2 wds. |
| 42% | SHERYLCROW | 10 | "All I Wanna Do" singer who performed the theme to "Tomorrow Never Dies": 2 wds. |
| 42% | BRUNOMARS | 9 | "The Lazy Song" singer who hosted and performed on "SNL" in 2012: 2 wds. |
| 42% | KELLYCLARKSON | 13 | "Piece by Piece" singer who performed "It's Quiet Uptown" on "The Hamilton Mixtape": 2 wds. |
| 41% | PAULMCCARTNEY | 13 | "Jet" singer who performed in the 2012 London Summer Olympics opening ceremony: 2 wds. |
| 41% | BRYANADAMS | 10 | "Heaven" singer who performed in the 2010 Vancouver Winter Olympics opening ceremony: 2 wds. |
| 40% | LEANNRIMES | 10 | "Blue" singer who performed in the 2002 Salt Lake City Winter Olympics opening ceremony: 2 wds. |
| 40% | BRITNEYSPEARS | 13 | "Toxic" singer who hosted and performed on "SNL" in 2000 and 2002: 2 wds. |
| 40% | KATYPERRY | 9 | "Roar" singer who's #11 on the 2013 Maxim Hot 100 List: 2 wds. |
| 40% | ARIANAGRANDE | 12 | "7 Rings" singer who was half the duet on 27-/31-Across: 2 wds. |
| 40% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 40% | JUSTINBIEBER | 12 | "Yummy" singer who was half the duet on 27-Across: 2 wds. |
| 39% | TINATURNER | 10 | "What's Love Got to Do With It" singer who performed the theme to "GoldenEye": 2 wds. |
| 39% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 39% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 39% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 39% | ELTONJOHN | 9 | "Rocket Man" singer who hosted and performed on "Saturday Night Live" in 2011: 2 wds. |
| 39% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| 39% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 39% | THEWEEKND | 9 | Stage name of "Starboy" singer who used the name for anonymity on YouTube: 2 wds. |
| 38% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 38% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |