| Occupation | Person | Hint |
| Rapper/Actor | |
| Sportscaster | |
| Record Producer | |
| Boxer | |
| Rapper | |
| Businessman | |
| Retired Baseball Player | |
| Mayor | |
| Football Player | |
| Retired Basketball Player | |
| Rapper | |
| Film/TV Producer | |
| Singer | |
| Rapper | |
| Singer | |
| Mayor | |
| | Occupation | Person | Hint |
| Retired Basketball Player | |
| Automaker | |
| Retired Football Player | |
| Business Mogul | |
| Retired Basketball Player | |
| Businessman | |
| Boxer | |
| Automobile Pioneer | |
| Government Official | |
| Retired Basketball Player | |
| Singer | |
| Businessman | |
| Pilot | |
| Businessman | |
| Singer | |
| Aviation Pioneer | |
|