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troperville

The Danza: In Season 4, Danny Strong plays Danny Siegel, Jane's cousin.
Executive Meddling: Resulted in a six-month delay to Season Five. Contentious negotiations between AMC and Matthew Weiner eventually led to a deal which included shortening episodes by two minutes, increased product placement, and possibly trimming the cast.
Hey, It's That Guy!:
- Elisabeth "Zoey Bartlet" Moss
  - Or, "A facially-burned mental patient"
- Christina "YoSaffBridge" Hendricks.
- While we're on Whedon shows, Vincent "Connor" Kartheiser
- And now Jonathan has gotten a job at SCDP in a stunning combination of nepotism and drunkenness. (It Makes Sense in Context.)
- In a magnificent case of Actor Allusion, Robert Morse as Bert Cooper, well-known for being J. Pierpont Finch, the deceptive, self-centered, rapidly rags-to-riches businessman in the early '60s musical farce How to Succeed in Business Without Really Trying.
- A number of cast members floated over from Jack And Bobby - Roger is Peter Benedict, Megan is Courtney Benedict, Joey is Jack McCallister.
- One of the recurring switchboard operators was Flo, The Progressive girl.
- Jimmy Barrett would go on to join The Dharma Initiative.
- Yet another switchboard operator, Nannette, was played by Kristen Schaal.
- Betty cheats on Don in the season two finale with Captain Awesome.
- Betty's brother is Ellis - or Jamie.
- Mr. Nigel Murray was Lane's secretary. Daisy Wicke is Peggy's roommate.
- Francine Hansen is Amber "Cutthroat Bitch" Volakis as well as creepy Alby's creepy wife.
- Finn DeTrolio is a Lenny Bruce-esque stand-up comic. And Carmine Lupertazzi Jr. is the concierge at Don and Megan's condominium.
- Lois's actress, Crista Flannigan, is possibly the only person who can say they've been in both Mad Men and Seltzer and Friedberg movies.
- Wait, is Eden McCain really just Don's neighbor, or is she spying on him for Primatech Paper?
- Lucille LaRusso is Ms Blankenship.
- I guess Jason Stackhouse isn't the only one Mrs. Newlin is trying to help find his way back to joy. And what the hell is Jane Bodehouse doing being Sally's psychiatrist?
- Ken Cosgrove is the future son-in-law of The Devil.
  - Don't you mean Leland Palmer?
  - And is married to Alex Mack.
  - And used to work as a detective.
  - A fun fact about that is that many of the Mad Men cast actually made cameo appearances in the above mentioned game.
- Maxwell Sheffield is one of Lane Pryce's bosses at PPL.
- Lisa Simpson works at the hospital where Betty had Eugene.
- Lane Pryce is an Alternate Universe Will Robinson, Dr. Ashford AND a bio-terrorist on Fringe not to mention his spectacular rise from criminal life.
  - Don't forget he's also Andy Warhol and now Professor Moriarty. Oh, and he's a big fan of Mickey and Mallory Knox.
  - Plus, his wife is Miss Honey from the film version of Matilda
- Don's daughter is Jinora.
- Annie Edison is married to Pete.
  - And her father is Marshall Darling
- Sexy Babysitter is married to Roger.
- Julia Ormond is Megan's mom.
- Paul Young? What are you doing at Sterling-Cooper? Or did you forget you are also Blanche Deveraux's illegitimate son?
- Pete has an affair Rory Gilmore!.
- Mr. Belding was one of the bigwigs at Cool Whip.
- Hey, when did Joyce (the confident lesbian photo editor at Life) get transformed into an insecure, straight college student?
- And why the hell does Reed Rockwell (AKA Bizzaro Nathan Ford) look like a clean-shaven Paul Kinsey?
- Don is having an affair with Lindsay Weir/Velma Dinkley, who's married to a doctor and lives in his building.
- Don and Megan almost have a four way with Jefferson Darcy and his wife!
- New partner Jim Culter slayed Medusa and a Kraken!
Life Imitates Art/The Red Stapler: Many of the period styles from the show have crept back into fashion.
The Other Darrin: Four different child actors have played Don's son Bobby.
Real-Life Relative:
- John Slattery's real life wife Talia Balsam plays Roger's wife Mona. Rather amusingly, their characters get divorced so that he can marry a twentysomething.
- Creepy little Glen Bishop is played by Matt Weiner's son.
Romance on the Set: Alexis Bledel (Beth Dawes) and Vincent Kartheiser (Pete Campbell) played two people in an affair in Season 5 (early 2012), officially started dating in October 2012, and got engaged in March 2013.
Star Making Role: For practically everyone on the show since the majority of the cast were unknowns or only known on niche shows before the series launched. The notable exception is Robert Morse, who has been a name for decades.
What Could Have Been:
- John Slattery originally auditioned for the role of Don Draper, but the production team felt he was too old.
- Jon Hamm originally auditioned for Jack Donaghy on 30 Rock. One wonders who they'd have cast as Don without Hamm.