| Singer Anthony | 14 |
| Singer Antoine from New Orleans | 31 |
| Singer Apple | 12 |
| Singer approaches N.Y.C. midtown oasis | 38 |
| Singer Arnold | 13 |
| Singer Artis Ivey, familiarly | 29 |
| Singer at "heaven's gate" | 39 |
| Singer at Barack's inauguration | 35 |
| Singer at Charles and Diana's wedding | 41 |
| Singer at Diana's funeral | 29 |
| Singer at Live 8 | 16 |
| Singer at McCartney's Gershwin Prize concert | 48 |
| Singer at Obama's 2009 inauguration | 39 |
| Singer at sea | 13 |
| Singer at shul | 14 |
| Singer at the chess match? | 26 |
| Singer at the Live Aid concert | 30 |
| Singer at Woodstock | 19 |
| Singer Autry | 12 |
| Singer Axton or pitcher Wilhelm | 31 |
| Singer Bachman | 14 |
| Singer backed by the Aliis | 26 |
| Singer backed by the Spiders From Mars | 38 |
| Singer Badu | 11 |
| Singer Baez | 11 |
| Singer Bailey | 13 |
| Singer Baker | 12 |
| Singer Baker or Bryant | 22 |
| Singer Baker or O'Day | 25 |
| Singer Baker with the 1988 hit "Giving You the Best That I Got" | 73 |
| Singer Bandy | 12 |
| Singer Barbara | 14 |
| Singer Barbara of Houston | 25 |
| Singer Barbra | 13 |
| Singer Bareilles | 16 |
| Singer Bareilles with the 2007 hit "Love Song" | 56 |
| Singer Bareilles with the 2007 top 10 hit "Love Song" | 63 |
| Singer Bareilles with the hit "Love Song" | 51 |
| Singer Barry | 12 |
| Singer Basil | 12 |
| Singer Basil or Braxton | 23 |
| Singer Basil who had a #1 hit with "Mickey" | 53 |
| Singer Basil who had the hit "Mickey" | 47 |
| Singer Basil with the #1 hit "Mickey" | 47 |
| Singer Bayes | 12 |
| Singer Bayes: 1880–1928 | 30 |
| Singer becomes golfer | 21 |
| Singer Bedingfield | 18 |
| Singer Bega | 11 |
| Singer behind prison walls? | 27 |
| Singer being treated for anxiety? | 33 |
| Singer Benatar | 14 |
| Singer Bennett | 14 |
| Singer Benton | 13 |
| Singer Berger | 13 |
| Singer Bernadette | 17 |
| Singer Berry | 12 |
| Singer Bette | 12 |
| Singer Bill . . . or a singing performance | 42 |
| Singer Bill known as the Cowboy Rambler | 39 |
| Singer Billie | 13 |
| Singer Billy | 12 |
| Singer Billy Ray | 16 |
| Singer Billy Ray -- | 19 |
| Singer Billy ___ | 16 |
| Singer Björk's birthplace | 32 |
| Singer Blacc | 12 |
| Singer Black | 12 |
| Singer Blige | 12 |
| Singer Blu with the 2001 hit "Hit 'Em Up Style (Oops!)" | 69 |
| Singer Bob | 10 |
| Singer Bob Marley, e.g. | 23 |
| Singer Bobbie ___ | 17 |
| Singer Bobby | 12 |
| Singer Bobby and family | 23 |
| Singer Bobby and others | 23 |
| Singer Bobby portrayed by Kevin Spacey | 38 |
| Singer Bobby ___: 1936-73 | 25 |
| Singer Bobby: 1936-73 | 21 |
| Singer Bobby: 1936–73 | 28 |
| Singer Bocelli | 14 |
| Singer Bon Jovi | 15 |
| Singer Bonnie | 13 |
| Singer Bono | 11 |
| Singer Boone | 12 |
| Singer born 5/24/41 | 19 |
| Singer born Anna Mae Bullock | 28 |
| Singer born Clara Ann Fowler | 28 |
| Singer born Dec. 12, 1915 | 25 |
| Singer born Eithne Nà Bhraonáin | 37 |
| Singer born Eithne Patricia Nà Bhraonáin | 46 |
| Singer born February 26 1932 | 29 |
| Singer born Helen Porter Mitchell | 33 |
| Singer born in Gaoth Dobhair | 28 |
| Singer born in Kaka'ako | 27 |
| Singer born in Lubbock, Texas in 1935 | 37 |
| Singer born in N.Y. | 19 |
| Singer born in Nigeria | 22 |
| Singer born in Trinidad | 23 |
| Singer born Katheryn Hudson | 27 |