| Singer Ross et al. | 18 |
| Singer Ross | 11 |
| Singer Ronstadt | 15 |
| Singer Ronnie | 13 |
| Singer Rogers | 13 |
| Singer Rod | 10 |
| Singer Roberta | 14 |
| Singer Robert | 13 |
| Singer Ritter | 13 |
| Singer Rita | 11 |
| Singer Riperton | 15 |
| Singer Rimes and others | 23 |
| Singer Rimes | 12 |
| Singer Ricky | 12 |
| Singer Richie | 13 |
| Singer Richard ___ -Bennet | 26 |
| Singer Ric | 10 |
| Singer Reznor | 13 |
| Singer Reeves | 13 |
| Singer Reese | 12 |
| Singer Reed or Rawls | 20 |
| Singer Reed | 11 |
| Singer Reddy | 12 |
| Singer Redding | 14 |
| Singer Redbone | 14 |
| Singer Ray with the Glenn Miller Orchestra | 42 |
| Singer Ray of the big band era | 30 |
| Singer Rawls or Reed | 20 |
| Singer Rawls | 12 |
| Singer Randy | 12 |
| Singer Raitt | 12 |
| Singer Raisa | 12 |
| Singer Rabbitt | 14 |
| Singer Quatro who played Leather Tuscadero on "Happy Days" | 68 |
| Singer Quatro | 13 |
| Singer profiled in "Sweet Dreams," 1985 | 49 |
| Singer profiled in "Sweet Dreams" | 43 |
| Singer profiled in ''Sweet Dreams'' | 51 |
| Singer Priest | 13 |
| Singer Pride's costume? | 27 |
| Singer Presley | 14 |
| Singer portrayed in film by Jennifer Lopez | 42 |
| Singer portrayed in ''Sweet Dreams'' | 52 |
| Singer portrayed by Spacey in "Beyond the Sea" | 56 |
| Singer portrayed by Spacek | 26 |
| Singer portrayed by Jennifer Lopez | 34 |
| Singer portrayed by Beyonce | 27 |
| Singer plus two, e.g. | 21 |
| Singer plus two | 15 |
| Singer played by Spacey | 23 |
| Singer played by Jennifer Lopez | 31 |
| Singer Pitney | 13 |
| Singer Pinza | 12 |
| Singer Piaf | 11 |
| Singer Phil | 11 |
| Singer Phair | 12 |
| Singer Petty | 12 |
| Singer Petina | 13 |
| Singer Peter of the duo Peter and Gordon | 40 |
| Singer Peter | 12 |
| Singer Pete of The Weavers | 26 |
| Singer Pete | 11 |
| Singer Perry with the 2010 #1 hit "Teenage Dream" | 59 |
| Singer Perry with the 2010 #1 hit "California Gurls" | 62 |
| Singer Perry | 12 |
| Singer Peniston with the 1991 hit "Finally" | 53 |
| Singer Peniston | 15 |
| Singer Pendergrass and others | 29 |
| Singer Pendergrass | 18 |
| Singer Peggy | 12 |
| Singer Peerce | 13 |
| Singer Peeples | 14 |
| Singer Payne | 12 |
| Singer Paula | 12 |
| Singer Paul ___ | 15 |
| Singer Paul with the 2005 album "Rock Swings" | 55 |
| Singer Paul who once said "I slice like a hammer" | 59 |
| Singer Paul who also wrote "Johnny's Theme" for "The Tonight Show" | 90 |
| Singer Paul from Ottawa | 23 |
| Singer Paul and family | 22 |
| Singer Paul | 11 |
| Singer Patti | 12 |
| Singer Patsy | 12 |
| Singer Pat from Brooklyn | 24 |
| Singer Pat | 10 |
| Singer part? | 12 |
| Singer part requiring footwork | 30 |
| Singer Pallett formerly known as Final Fantasy | 46 |
| Singer Paisley | 14 |
| Singer Page or LaBelle | 22 |
| Singer Page | 11 |
| Singer Osmond | 13 |
| Singer Orlando | 14 |
| Singer Orbison | 14 |
| Singer or Petty | 15 |
| Singer or Italian lake | 22 |
| Singer or composer | 18 |
| Singer or color | 15 |
| Singer or bearer | 16 |
| Singer or actor's helper | 28 |