| Hint | Person |
| Blues Guitarist | |
| Poet, Lincoln biographer | |
| Lead singer of Smashing Pumpkins | |
| Founder of a media empire | |
| Outspoken manager of the White Sox | |
| Famous Film Critic | |
| Actor in Swingers, among others | |
| One half of the Blues Brothers | |
| Famous Gangster, portrayed by Robert DeNiro | |
| Political Activist, former presidental candidate | |
| Rapper who likes to interrupt people | |
| Bank Robber, killed outside Chicago theatre | |
| Hizzoner (Former Mayor) | |
| Disgraced crazy hair governor | |
| R&B Singer who likes closets | |
| Actor, most famous for holding up a boom box | |
| Attorney General under George W. Bush | |
| | Hint | Person |
| Founder of famous magazine | |
| Actor, known for going after gophers | |
| Da Coach | |
| Famous architect | |
| NORM!!! | |
| Legendary Cubs/White Sox Announcer | |
| 'Unforgettable' singer | |
| Hi Bob! | |
| Held NFL Record for Rushing Yards | |
| Greatest NBA Player of all time | |
| Current Sec. of State | |
| I Pity the Fool! | |
| Late girthy SNL alumus | |
| Nobel Winning Physicist | |
| Chicago Bear Legend, also starred in 'My Two Dads' | |
| 44th President of the United States | |
| Director known for his 80's teen movies | |
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