According to Jim Croce, Leroy Brown is the baddest man in the whole damn town.  The downtown ladies call him “treetop lover,” what do all the man call him?

This Robert Johnson classic Chicago song was famously covered by what sunglasses-wearing duo, in a movie that shares their name?

Name the Chicago-based band whose breakout fourth album features the Marina City towers on the cover.

Hint: they are trying to break your heart

Djo is his musician name, and in his 2024 hit he told us what it feels like when he’s back in Chicago, promising that “you take the man out of the city, not the city out the man.” What hit Netflix TV show does he star in?

Lyrics. Fill in the Blank:

They have the time, the time of their life

I saw a man, he ___ ___ ___ ___

Name the Chicago Band who sang:

Tonight, tonight

And you know you’re never sure

But you’re sure you could be right

If you held yourself up to the light?

And the embers never fade

In your city by the lake

The place where you were born.

What notorious Chicago gangster is referenced in Paper Lace’s 1974 hit “The Night Chicago Died”

Name the artist whose song "Chicago" was the theme song for the Netflix show The Politician, and was featured in an episode of The Bear, and in films Veronica Mars (2014), and Little Miss Sunshine (2006).

Hint: “All things go.”

Name this “Chi-city” rapper. Born and raised in Chicago, he’s a triple threat: actor, rapper, and activist.

Lyric, Fill in the Blank:

“I got my city doin’ ____ ____”

Lyrics, Fill in the Blank:

And each time I roam

Chicago is ____ ____ ____

Lyrics, Fill in the Blank:

And there ain’t no road just like it

Anywhere I found

Running south on Lake Shore Drive ____ ____ ____