| Riddle | Answer | Song Released in |
| Where did the Red Hot Chili Peppers say is the worst place to stand in San Francisco during an earthquake? | |
| What did Britney Spears say when the disco club became too loud to be enjoyable? | |
| What did Journey ask in exasperation when each of the kids they were babysitting threw tantrums throughout the day? | |
| How did Justin Timberlake describe his Anna Kournikova-themed tramp stamp? | |
| How often do Nelly and Tim McGraw like to get intimate with each other? | |
| How did Mariah Carey describe her 24 hours in the candy store with Boyz II Men? | |
| How did Christina Aguilera describe her situation in the midst of amazing home renovation projects? | |
| What does Miranda Lambert use to fill her revolver and mechanical pencil, respectively? | |
| What was the first thing Rob Thomas stole when he robbed a rich old woman? | |