1. Corinne or Cory.
2. Chuck Adamson.
3. Manny Weisbord, probably based on Meyer Lansky. Joseph Wiseman's most famous role was as Dr. No in the first James Bond film.
4. False. But famous people who appeared on the show include Kevin Spacey in one episode as a Kennedyesque senator and Debbie Harry as Bambi, the high-end prostitute who is with Luca for a while.
5. Ann is a librarian.
6. The key is the episode "Hearings" in which the Tonkin Gulf incident is announced, starting the Vietnam War and signaling the end is near of the wonderful era the show is set in. "The '60s" as most people think of them are about to start. That was in August 1964.
7. Ha ha, a trick question! They don't tell us so we don't know! It's in South America south of the equator.
8. Jann Wenner, co-founder and publisher of Rolling Stone.
9. Wes Connelly, Torello's friend who "came up" with him in the Chicago police. Luca shoots him in the back of the head in a phone booth after he catches Connelly following him. Nate Grossman replaced him in the MCU.
10. Bronze Star for bravery in combat.
11. Pochenko. He wanted to meet Elvis Presley.
12. Frank Holman.
13. Phil Bartoli.
14. The Patch.
15. His accent! Dennis Farina and John Santucci (also the show's technical adviser) are obviously really from Chicago with very broad, flat accents. Anthony Denison (on TNT's "The Closer" as of 2009) has a slight New York accent. Italian-Americans don't all sound alike!
16. Izzy (short for Israel?).
17. Suzanne Terry, a magazine reporter, played by Pam Grier, famous for '70s blaxploitation films. That's why her relationship with Abrams was controversial in 1963 Chicago including with some blacks (in 1963-64 people said "Negroes") like Walt Clemmons in the MCU/Strike Force: she's black so it was interracial (black-white).
18. Joanne. Ray Luca seduces her just for the power of it.
19. Ted Kehoe. Luca uses him as a puppet to take over a pension fund but he turns on and slugs Luca when Luca murders his fiancée. When Kehoe stupidly tells Luca he'll tell on him, Luca and Pauli Taglia push him through a high-rise window.
20. Black 1959 Ford Galaxie.
21. Miles Davis.
22. Polish. They speak it to each other and in "Abrams for the Defense" when the nasty landlord Sturkowski (a 1950 refugee from the Communists) berates Krychek for siding with a black man (whom he calls an animal) against "your own people" Krychek says to him "You're not my people!" and then in his language, "A ty prosto swinja! Rozumiesz?" (You're just a pig! Understand?)
23. "Keep Searching."
24. Pauli Taglia may not seem very bright but John Santucci was a master jewel thief.
25. Dennis Farina once arrested John Santucci.