| Singer with a gang | 18 |
| Singer with a Latin beat? | 25 |
| Singer with a negative-sounding name | 36 |
| Singer with a palindromic name | 30 |
| Singer with a punctuated name | 29 |
| Singer with a reputation for being self-centered | 48 |
| Singer with a short-lived 1950s sitcom | 38 |
| Singer with a song about Alice | 30 |
| Singer with a star on Canada's Walk of Fame | 47 |
| Singer with a wide range | 24 |
| Singer with an ego | 18 |
| Singer with an Oscar-nominated song from "Robin Hood" | 63 |
| Singer with an Oscar-nominated song in "The Lord of the Rings" | 72 |
| Singer with attitude | 20 |
| Singer with backup, often | 25 |
| Singer with bandleader Xavier Cugat | 35 |
| Singer with Brooks | 18 |
| Singer with Count and Duke | 26 |
| Singer with Crosby and Stills | 29 |
| Singer with Crosby, Stills & Nash | 37 |
| Singer with Cugat | 17 |
| Singer with Cult Jam | 20 |
| Singer with Dolly Parton and Linda Ronstadt on the album "Trio" | 73 |
| Singer with Duke | 16 |
| Singer with four recent best-selling albums of pop standards | 60 |
| Singer with Krupa's orchestra | 33 |
| Singer with Louis and Duke | 26 |
| Singer with lowercase initials | 30 |
| Singer with medical training? | 29 |
| Singer with multiple "Farewell Tours" | 47 |
| Singer with Parliament and Funkadelic | 37 |
| Singer with reggae's Melody Makers | 38 |
| Singer with Sonny once, | 23 |
| Singer with stars on Hollywood's and Canada's Walks of Fame | 67 |
| Singer with the #1 album "Between the Lines" | 54 |
| Singer with the #1 country album "80's Ladies" | 60 |
| Singer with the #1 country hit "Hello Darlin'" | 60 |
| Singer with the #1 hit "All I Have" | 45 |
| Singer with the #1 hit "Don't Forbid Me" | 54 |
| Singer with the #1 hit "To Sir With Love" | 51 |
| Singer with the #1 R&B hit "I Feel for You" | 57 |
| Singer with the #1 R&B hit "You'll Never Find Another Love Like Mine" | 87 |
| Singer with the 1941 hit "San Antonio Rose" | 53 |
| Singer with the 1954 #1 hit "This Ole House" | 54 |
| Singer with the 1960 #1 album "G.I. Blues" | 52 |
| Singer with the 1963 hit "If I Had a Hammer" | 54 |
| Singer with the 1964 #2 hit "My Boy Lollipop" [the Bushes 41] | 71 |
| Singer with the 1965 hit "1-2-3" | 42 |
| Singer with the 1966 hit "I'm So Lonesome I Could Cry" | 68 |
| Singer with the 1971 hit "Mercy Mercy Me" | 51 |
| Singer with the 1974 #1 hit "Rock Me Gently" | 54 |
| Singer with the 1975 #1 hit "Lady Marmalade" | 54 |
| Singer with the 1980 #1 album "Against the Wind" | 58 |
| Singer with the 1980 #1 album "Guilty" | 48 |
| Singer with the 1980 #1 hit "Upside Down" | 51 |
| Singer with the 1983 #2 hit "Electric Avenue" | 55 |
| Singer with the 1984 hit "Caribbean Queen" | 52 |
| Singer with the 1986 #1 album "Promise" | 49 |
| Singer with the 1988 #1 country hit "I'm Gonna Get You" | 69 |
| Singer with the 1988 Top Ten Hit "Walk on Water" | 58 |
| Singer with the 1990 #1 album "To the Extreme" | 56 |
| Singer with the 1991 #1 hit "Rush, Rush" | 50 |
| Singer with the 1992 album "Ingénue" | 49 |
| Singer with the 1992 album "Joshua Judges Ruth" | 57 |
| Singer with the 1992 quintuple-platinum album "Shepherd Moons" | 72 |
| Singer with the 1993 multi-platinum album "Music Box" | 63 |
| Singer with the 1994 #1 alternative rock hit "God" | 60 |
| Singer with the 1994 #1 hit "Bump N' Grind" | 57 |
| Singer with the 1994 #1 hit "Stay" | 44 |
| Singer with the 1994 hit "Bump n' Grind" | 54 |
| Singer with the 1994 hit "You Gotta Be" | 49 |
| Singer with the 1995 album "Velvet and Brass" | 55 |
| Singer with the 1996 #1 hit "You're Makin' Me High" | 69 |
| Singer with the 1996 Grammy-winning album "Falling Into You" | 70 |
| Singer with the 1996 triple-platinum album "Tidal" | 60 |
| Singer with the 1997 album "Drag" | 43 |
| Singer with the 1998 hit 'Save Tonight' | 47 |
| Singer with the 1999 #1 hit "Believe" | 47 |
| Singer with the 1999 #1 hit "If You Had My Love" | 58 |
| Singer with the 1999 album "To the Teeth" | 51 |
| Singer with the 2000 #1 hit "Be With You" | 51 |
| Singer with the 2000 album "Lovers Rock" | 50 |
| Singer with the 2001 album "Vespertine" | 49 |
| Singer with the 2002 hit "Ignition" | 45 |
| Singer with the 2004 album "Encore" | 45 |
| Singer with the 2006 album "Testimony: Vol. 1, Life & Relationship" | 81 |
| Singer with the 2007 hit "1234" | 41 |
| Singer with the 2008 album "New Amerykah Part One (4th World War)" | 76 |
| Singer with the 2008 gold record "And Winter Came ..." | 64 |
| Singer with the 2009 #1 hit 'Tik Tok' | 45 |
| Singer with the 2009 #1 hit "Poker Face" | 50 |
| Singer with the 2009 hit "Tik Tok" | 44 |
| Singer with the 2010 #1 hit "Tik Tok" | 47 |
| Singer with the 2011 "Get $leazy" tour | 48 |
| Singer with the 2011 album '21' | 39 |
| Singer with the 2011 single "California" | 50 |
| Singer with the 2012 hit "Let Me Love You (Until You Learn to Love Yourself)" | 87 |
| Singer with the 2013 #1 "Royals" | 42 |
| Singer with the 2013 #1 hit "Roar" | 44 |
| Singer with the 2014 top 10 hit "Boom Clap" | 53 |