| Singer Henley | 13 |
| Singer Hilson | 13 |
| Singer honored on a 2008 U.S. postage stamp | 43 |
| Singer Horne | 12 |
| Singer Horne and actress Olin | 29 |
| Singer Horne and others | 23 |
| Singer Houston | 14 |
| Singer Howard | 13 |
| Singer Ian | 10 |
| Singer Iglesias | 15 |
| Singer Iglesias 31. Fourth-down plays | 37 |
| Singer Imbruglia | 16 |
| Singer in 1977's Best Picture | 33 |
| Singer in a boîte | 20 |
| Singer in a brawl? | 18 |
| Singer in a fatal plane crash on February 3, 1959 | 49 |
| Singer in a field | 17 |
| Singer in a group | 17 |
| Singer in a legendary band | 26 |
| Singer in a Salinger story | 26 |
| Singer in Abba | 14 |
| Singer in an interrogation room? | 32 |
| Singer in black | 15 |
| Singer in Bob Dylan's Rolling Thunder Revue | 47 |
| Singer in no. 50 | 16 |
| Singer in old Muriel Cigars ads | 31 |
| Singer in the "Lady Marmalade" remake | 47 |
| Singer in the "Odyssey" | 33 |
| Singer in the 1954 film "Secret of the Incas" | 55 |
| Singer in the 1958 movie "Go, Johnny, Go!" | 52 |
| Singer in the Gaming Hall of Fame | 33 |
| Singer in the John Wayne film "The Longest Day" | 57 |
| Singer in the sea, literally | 28 |
| Singer in the Whiffenpoofs | 26 |
| Singer in white buck shoes | 26 |
| Singer India | 12 |
| Singer India ___ | 16 |
| Singer India.-- | 15 |
| Singer India.__ | 15 |
| Singer India.___ | 16 |
| Singer inducted into the Rock and Roll Hall of Fame in 2000 | 59 |
| Singer Irene | 12 |
| Singer Irene who won a 1983 songwriting Oscar | 45 |
| Singer Irene ___ | 16 |
| Singer Isaac who cowrote "Soul Man" | 45 |
| Singer Ives | 11 |
| Singer J. J. | 12 |
| Singer Jack of "Louie, Louie" fame | 44 |
| Singer Jackson | 14 |
| Singer Jackson -- | 17 |
| Singer Jackson et al. | 21 |
| Singer Jackson with more than 20 #1 country hits | 48 |
| Singer Jacques | 14 |
| Singer Jacques and family | 26 |
| Singer James | 12 |
| Singer James and namesakes | 26 |
| Singer James and others | 23 |
| Singer James et al. | 19 |
| Singer James from L.A. | 22 |
| Singer James or Jones | 21 |
| Singer James or Mitchell | 24 |
| Singer Jamie with the 2001 #1 country song "When I Think About Angels" | 80 |
| Singer Jan | 10 |
| Singer Jane Siberry's new name, as of 2006 | 46 |
| Singer Janelle with "Tightrope" | 41 |
| Singer Janet Baker et al. | 25 |
| Singer Janet Baker's title | 30 |
| Singer Janis | 12 |
| Singer Janis with the hit album "Between the Lines" | 61 |
| Singer Janis ___ | 16 |
| Singer Jann | 11 |
| Singer Jarreau and others | 25 |
| Singer Jason | 12 |
| Singer Jennifer | 15 |
| Singer Jennifer's new son? | 30 |
| Singer Jenny | 12 |
| Singer Jerry | 12 |
| Singer Jerry -- Lewis | 22 |
| Singer Jerry from N.Y.C. | 24 |
| Singer Jerry Lee | 16 |
| Singer Jerry ___ | 16 |
| Singer Jerry ___ Lewis | 22 |
| Singer Jett with the Blackhearts | 32 |
| Singer Jewel, e.g. | 18 |
| Singer Jim | 10 |
| Singer Jim and others | 21 |
| Singer Jimmy or Bill | 21 |
| Singer Joan | 11 |
| Singer Joan with The Blackhearts | 32 |
| Singer Joe and actor Ron | 24 |
| Singer Joey with the 60's Starliters | 40 |
| Singer John | 11 |
| Singer John and family | 22 |
| Singer John and namesakes | 25 |
| Singer John and others | 22 |
| Singer John from Middlesex | 26 |
| Singer John from punk legends X, appropriately | 46 |
| Singer John of Middlesex | 24 |
| Singer John of musicals | 23 |
| Singer John of Steppenwolf | 26 |