1. About Last Night
Director Ed Zwick; writer David Mamet (see the footnote, or “Bonus” section)
Stars Jennifer Jason Leigh and Scott Glenn
3. Blues Brothers
Writer/director John Landis; cameo by Carrie Fisher
4. Breakfast Club
Stars Ally Sheedy and Judd Nelson (who is discussed in Ally’s Bonus section)
5. Brian’s Song
Star James Caan (discussed in his son Scott’s bio)
Songwriters Kander & Ebb (see the Bonus)
7. Dark Knight
Star Maggie Gyllenhaal
8. Doctor Detroit
Star Fran Drescher
9. Eight Men Out
Star Michael Lerner of When Do We Eat?
10. Ferris Bueller’s Day Off
Stars Matthew Broderick and Jennifer Grey; cameo by Ben Stein
11. The Fugitive
Star Harrison Ford
12. High Fidelity
Stars Jack Black and Lisa Bonet
13. Home Alone
Star Daniel Stern
14. I Want Someone to Eat Cheese With
Writer/director/star Jeff Garlin, stars Sarah Silverman, Paul Mazursky, and Richard Kind
15. My Best Friend’s Wedding
Maybe writer Ronald Bass...?
16. My Big Fat Greek Wedding
Star Lainie Kazan
17. My Bodyguard
Nada. Star Ruth Gordon plays a Holocaust survivor in Harold and Maude and a Jewish mother in Where’s Poppa, though.
18. Planes, Trains & Automobiles
I’m 90% sure actor Larry Hankin is, and…
19. Risky Business
…I’m also pretty sure director Paul Brickman is. Anyone with info on these two, please send it on.
20. Road to Perdition
Stars Paul Newman and Jennifer Jason Leigh
21. The Sting
Star Paul Newman
22. Stranger Than Fiction
Stars Maggie Gyllenhaal and Dustin Hoffman
23. The Untouchables
Actor Steven Goldstein
24. When Harry Met Sally
Stars Billy Crystal, Carrie Fisher. Director/star Rob Reiner; cameo by his mom (“I’ll have…”). Writer Nora Ephron. Soundtrack performed by Harry Connick Jr., mostly of songs written by Jews.
25. While You Were Sleeping
Star Jack Warden
There are at least 25 other good movies set in Chicago, so look for this post’s sequel in the months to come.