The Windy City

I'm traveling this weekend — send me your Chicago recommendations!

Welcome to Jacob’s Letter, a free pop culture newsletter full of puns and dog photos. I’ll be out of town this week headed to Chicago for a wedding, so this week’s issue will be shorter and will be about Chicago, the Windy City (and a very cold city, hence Opal’s Jimmy Buffett cap here).

I figured I would use this as a way to just share my favorite pieces of Chicago pop culture. Enjoy.

Kanye’s “Homecoming”:

All of Chance’s “Coloring Book”:

All of Lupe’s “The Cool”:

Obviously, “Cell Block Tango” from “Chicago”:

Spike Lee’s “Chi-Raq”:

This scene from “Widows” specifically but also all of “Widows” in general:

The Ferris Bueller parade:

• Also, anything Gillian Flynn has ever written

• Anything Roger Ebert has ever written

And, of course…

Sinatra:

That’s all, folks. If you liked what you saw here, click that subscribe button (promise I won’t send any annoying emails) and tell all your friends!

If there’s anything you want to see covered in a future newsletter, let me know!

You can find me in other corners of the internet as well, if you so choose. There’s my personal website (which focuses on pop culture, faith and my journalism clips), a Twitter account and a Letterboxd account. Subscribe away.

See you next week,

Jake