Fan Art Thursdays — All-Star Mad Men Cast in the 60’s

 Posted by on November 3, 2011 at 6:55 am  Fan Art
Nov 032011

I got to wondering the other day, how would Mad Men be cast if it was made into a movie in the 1960’s?   The wheels turned in my mind and several of these actors immediately popped in there.  My go-to for Pete was Disney legend Tommy Kirk–an amazing resemblance to Vincent K!  And naturally Grace Kelly for Betty and Orson Welles for Paul! (yeah, I know that Grace was already a Princess in the 60’s, but you see, she came out of retirement just to play Betty!)  See who’s who, how many you recognize, and  bonus points to those of you who pick out the two Star Trek  guest stars! (you know who you are)  Enjoy my fantasy all-star cast for Mad Men: The Movie. (Click on art to see full size)  (NOTE: 10:34 p.m. I have now added Dana Wynter as Mona!


  28 Responses to “Fan Art Thursdays — All-Star Mad Men Cast in the 60’s”

  1. Excellent, all around!

    (I’m partial to the Jackie Gleason choice, FWIW)

  2. I love this! I remember all these folks in their heyday & this is truly a dream cast….

  3. Love Rock Hudson as Sal! What perfect casting that would be! LOL!! Not to mention Burl Ives as Bert Cooper and Joanne Woodward as Peggy. Pure Gold!

  4. Thanks Less of me,not Bridget, and Jen — I loved Jackie Gleason too–If MM was a movie in the 60’s, I can hear the Jackie Gleason theme from his variety show as the soundtrack:

  5. Oh, I love it!

  6. Brilliant!

    I figured it out except not sure who Marlo Thomas and Natalie Wood are. Midge and Rachel? Rachel and Midge?

  7. isn;t Marlo Thomas Trudy?

    And i’d guess the last two are midge and rachel or the teacher and bobbie.

  8. “And the Children Shall Lead” and “Metamorphosis” 😉

  9. Probably not what you had in mind, but I just pictured Marlo Thomas behind the wheel of a John Deere.

  10. MRM definitely, Marlo as Ann Marie would make a good Lois! But here, she’s a very fashionable MM member! Look closely at the costumes and you’ll figure out who the ladies are!

    #8 You are correct! 😉 I especially like the expression on Ms. Donahue’s face!

  11. we, so who is supposed to be whom?

  12. Cheat Sheet!

    The Men –
    Don, Roger, Peter, Bert, Sal, Harry, Paul, Ken, and Freddie

    The Women –
    Betty, Joan, Peggy, Trudy, Sally, Midge, and Rachel

    I’m thinking now I should have found someone to be Mona! Any ideas?
    How’s the skyline? NYC enough? I had fun creating it!

  13. How about Louise Latham as Mona?

  14. Matt, I looked up Louise Latham and recognized her immediately from Hitchcock’s “Marnie”, but I think she’s just a tad too old — however, I have found my perfect Mona thanks to your suggestion —

    Keep checking back here as I will amend the poster to add Mona!

  15. Brava! It’s perfect.

  16. Love this.

  17. Stunning all around. 🙂

  18. It’s wonderful. It looks like an old movie poster. Thanks for providing the cheat sheet.

  19. And Now — we have Mona Sterling! Dayna Winter seemed perfect! Mature, but still as glam as ever! Balances out the ladies too. Now it’s done!

    Here’s the updated cheat sheet:

    The Men –
    Don, Roger, Peter, Bert, Sal, Harry, Paul, Ken, and Freddie

    The Women –
    Betty, Joan, Peggy, Mona, Trudy, Sally, Midge, and Rachel

  20. #14: I think Latham in the 1960’s was about the same age as today’s Mona. AND she was made up to look OLDER (dead, in fact) for Marnie. So, with brunette hair and younger make-up, she could fill the bill.

    FWIW, Diane Baker would be too young. 😉

  21. Oh yeah, Diane Baker would probably be Margaret Sterling! But I do like Dana Wynter as Mona, remember her from the original Invasion of the Body Snatchers?

  22. Fabulous! hahaha! Tks for this Therese :O)

  23. Don could only have been played by Gregory Peck – Don (and Jon Hamm himself, for that matter) seem almost modeled on Peck, even if the perfect age match would have been Peck of the 50s. In season 1, someone even refers to Don as “The Man in the Grey Flannel Suit”. Take a look at the poster displayed on that film’s Wikipedia page.

  24. I’ve been giving this some thought – while it’s cool to pick actors who look like their modern-day counterparts, they may not necessarily be right for part.

    For instance – Jeff Chandler would be all wrong for Roger, he did have that reckless lightheartedness about him.

    Burl Ives would be too young to play Bert,and Allan Sherman and Orson Welles were too old to play their suggested parts. (and there would be no way Rock Hudson would play a character like Sal)

    However, Tommy Kirk as Pete does work – just take a look at him in what is considered his best dramatic role in Old Yeller – he never really got a chance to do many dramatic roles.

    Gleason as Freddie might be interesting.

    I’d have to give some thoughts on the casting of the ladies.

    Now let’s look past the look of the actors playing the parts now – and think just of the character descriptions in the show “Bible” and the pilot.

    Let me throw out a name I might cast in a c.1964 MAD MEN – For the Part of Roger Sterling – Peter Lawford. (using an American accent) he could deliver those great witty lines. I’m thinking of him in the 1950’s THE THIN MAN TV series where there were touches of humor with the drama/mystery.

    More Thoughts to Follow.

  25. Wow! Thanks Herb and Berkowit!

    I admit, I cast this mostly on looks, but some of them (like Woodward as Peggy and Gina as Joan) would be perfect!

    I agree that Gregory Peck would make a beautiful Don Draper, but Peck was such a wonderfully nice guy, I just didn’t want to make him nasty like Don. I chose an ‘unknown’ — Tom Tryon was a b-picture star who reminded me of Don. Same intense looks, although Peck was a much better actor.
    Tommy Kirk was fired from Disney when Uncle Walt discovered that Tommy was gay, but let him come back for ‘The Monkey’s Uncle’ because “Merlin Jones had been such a hit.
    That photo of Burl Ives was from “Cat on a Hot Tin Roof” where he played ailing Big Daddy, he could pull off Bert.
    I chose Alan Sherman because he was the only husky 60’s celebrity I could find that wore horn rim glasses!
    I know Orson Welles was older at this time, so I used a younger picture of him form the ’30s! (The Paul resemblance is amazing)
    No Rock probably wouldn’t do it, but it’s a fantasy cast.
    Gleason had his share of dramatic roles (Gigot, anyone?) and he could break your heart. He’d make a hell of a Freddie.
    Peter Lawford as Roger? Could be, could be. But I chose Jeff for his silver fox element and intensity. Thanks for the input, and by all means lets see your dream casts!

  26. This is too cute, Therese! Very creative–thanks for sharing.

  27. Thanks Mad! I had fun creating it — I’m especially proud of the skyline!

  28. Thelma Ritter as Miss Blankenship! I just looked her up, and she worked until 1968, the year before her death at 66.

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