| Singer with the 1994 #1 hit "Bump N' Grind" | 57 |
| Singer with the 1994 #1 alternative rock hit "God" | 60 |
| Singer with the 1993 multi-platinum album "Music Box" | 63 |
| Singer with the 1992 quintuple-platinum album "Shepherd Moons" | 72 |
| Singer with the 1992 album "Joshua Judges Ruth" | 57 |
| Singer with the 1992 album "Ingénue" | 49 |
| Singer with the 1991 #1 hit "Rush, Rush" | 50 |
| Singer with the 1990 #1 album "To the Extreme" | 56 |
| Singer with the 1988 Top Ten Hit "Walk on Water" | 58 |
| Singer with the 1988 #1 country hit "I'm Gonna Get You" | 69 |
| Singer with the 1986 #1 album "Promise" | 49 |
| Singer with the 1984 hit "Caribbean Queen" | 52 |
| Singer with the 1983 #2 hit "Electric Avenue" | 55 |
| Singer with the 1980 #1 hit "Upside Down" | 51 |
| Singer with the 1980 #1 album "Guilty" | 48 |
| Singer with the 1980 #1 album "Against the Wind" | 58 |
| Singer with the 1975 #1 hit "Lady Marmalade" | 54 |
| Singer with the 1974 #1 hit "Rock Me Gently" | 54 |
| Singer with the 1971 hit "Mercy Mercy Me" | 51 |
| Singer with the 1966 hit "I'm So Lonesome I Could Cry" | 68 |
| Singer with the 1965 hit "1-2-3" | 42 |
| Singer with the 1964 #2 hit "My Boy Lollipop" [the Bushes 41] | 71 |
| Singer with the 1963 hit "If I Had a Hammer" | 54 |
| Singer with the 1960 #1 album "G.I. Blues" | 52 |
| Singer with the 1954 #1 hit "This Ole House" | 54 |
| Singer with the 1941 hit "San Antonio Rose" | 53 |
| Singer with the #1 R&B hit "You'll Never Find Another Love Like Mine" | 87 |
| Singer with the #1 R&B hit "I Feel for You" | 57 |
| Singer with the #1 hit "To Sir With Love" | 51 |
| Singer with the #1 hit "Don't Forbid Me" | 54 |
| Singer with the #1 hit "All I Have" | 45 |
| Singer with the #1 country hit "Hello Darlin'" | 60 |
| Singer with the #1 country album "80's Ladies" | 60 |
| Singer with the #1 album "Between the Lines" | 54 |
| Singer with stars on Hollywood's and Canada's Walks of Fame | 67 |
| Singer with Sonny once, | 23 |
| Singer with reggae's Melody Makers | 38 |
| Singer with Parliament and Funkadelic | 37 |
| Singer with multiple "Farewell Tours" | 47 |
| Singer with medical training? | 29 |
| Singer with lowercase initials | 30 |
| Singer with Louis and Duke | 26 |
| Singer with Krupa's orchestra | 33 |
| Singer with four recent best-selling albums of pop standards | 60 |
| Singer with Duke | 16 |
| Singer with Dolly Parton and Linda Ronstadt on the album "Trio" | 73 |
| Singer with Cult Jam | 20 |
| Singer with Cugat | 17 |
| Singer with Crosby, Stills & Nash | 37 |
| Singer with Crosby and Stills | 29 |
| Singer with Count and Duke | 26 |
| Singer with Brooks | 18 |
| Singer with bandleader Xavier Cugat | 35 |
| Singer with backup, often | 25 |
| Singer with attitude | 20 |
| Singer with an Oscar-nominated song in "The Lord of the Rings" | 72 |
| Singer with an Oscar-nominated song from "Robin Hood" | 63 |
| Singer with an ego | 18 |
| Singer with a wide range | 24 |
| Singer with a star on Canada's Walk of Fame | 47 |
| Singer with a song about Alice | 30 |
| Singer with a short-lived 1950s sitcom | 38 |
| Singer with a reputation for being self-centered | 48 |
| Singer with a punctuated name | 29 |
| Singer with a palindromic name | 30 |
| Singer with a negative-sounding name | 36 |
| Singer with a Latin beat? | 25 |
| Singer with a gang | 18 |
| Singer with a falsetto | 22 |
| Singer with a distinctively spelled first name | 46 |
| Singer with a deep voice | 24 |
| Singer with a black V-shaped collar | 35 |
| Singer with a Best Actress Oscar | 32 |
| Singer with a 1978 #1 hit with Barbra Streisand | 47 |
| Singer with a 1962 #1 hit that started a dance craze (and a hint to this puzzle's theme) | 92 |
| Singer with a "Best of" album titled "Paint the Sky With Stars" | 83 |
| Singer with 11 #1 country hits prepares letters for mailing? | 60 |
| Singer with "The Gang" | 32 |
| Singer Winwood | 14 |
| Singer Winehouse after marrying artist Albrecht | 47 |
| Singer Winehouse | 16 |
| Singer Winans | 13 |
| Singer Wilson | 13 |
| Singer Willie | 13 |
| Singer Williams | 15 |
| Singer whose surname is Kilcher | 31 |
| Singer whose pastime is making beer? | 36 |
| Singer whose name sounds like an Olympic speed skater | 53 |
| Singer whose name sounds like a cry | 35 |
| Singer whose name is written in lower case | 42 |
| Singer whose name is an anagram of "enlarge" | 54 |
| Singer whose music plays in new age stores | 42 |
| Singer whose middle name is Hercules | 36 |
| Singer whose life was made into a 1980 hit play | 47 |
| Singer whose last name is Chrysomallis | 38 |
| Singer whose first top 10 hit was "Where Does My Heart Beat Now" | 74 |
| Singer whose band just appeared unannounced in your iTunes collection | 69 |
| Singer whose backup group was called the Aliis | 46 |
| Singer whose back-up band was the Full Tilt Boogie | 50 |
| Singer whose 2002 song "Foolish" was #1 for 10 weeks | 62 |