An article in the Montreal Gazette provides this juicy Matthew Weiner quote:

The culture views the ’60s as this kind of golden glory. The election of John F. Kennedy is memorialized as a time of great innocence. And yet, reading the New Yorker from April 1960 and reading the movie reviews in there of Psycho and The Apartment, I thought to myself, ‘This is not a particularly innocent society.’ We forget that the wave of youth and enthusiasm that swept the country then was decided by about 100 votes.

Psycho and The Apartment? Where have I heard that before? Oh, yeah. Here’s a Mad Men conversation about The Apartment:

Aw, Red, that’s not how it is. Look, it was crude. That’s the way pictures are now. Did you see that ridiculous Psycho? Hollywood isn’t happy unless things are extreme.

Roger Sterling to Joan Holloway, Long Weekend

What were the big movies of 1960? I perused the IMDb (it’s like a home to me) and found:
The Apartment
Inherit the Wind
BUtterfield 8
Elmer Gantry
Midnight Lace
Little Shop of Horrors
Ocean’s Eleven
The Alamo
Murder, Inc.
Sons and Lovers
The Sundowners

I haven’t seen all of them, but there are some definite themes. They are movies about distrust, betrayal by authority, sexuality, isolation, sexuality that is isolating, religious tyrants, and noble rebellion against oppressive authority.

In the Great Hooker Oscars of 1961, Elizabeth Taylor won the Best Actress award for playing a whore in BUtterfield 8, defeating Shirley Maclaine’s tragic “other woman” in The Apartment; while Shirley Jones won Best Supporting Actress for playing a whore in Elmer Gantry, defeating Janet Leigh’s frankly sexual portrayal in Psycho. Heady stuff, and, while the previous year’s award show wasn’t exactly tame (Suddenly, Last Summer and Anatomy of a Murder saw to that), Ben-Hur, Some Like It Hot and Pillow Talk were considerably more wholesome.

Perversity plays a role in Little Shop of Horrors as well as Psycho. Spartacus and Exodus are optimistic fights against oppression, and praise religion as they fight authority, but Inherit the Wind and Elmer Gantry show the dark side of religious authority, and The Apartment is a screed against institutional authority, which destroys decent men and women unless they fight back.

The overall effect is remarkably dark, even though this is also the year of Pollyanna and Please Don’t Eat the Daisies. The world is a dangerous place, twisting us up and spitting us out, turning women into whores and men into slaves and pawns.

For Mad Men Season 2, some interesting movies show up. 1962 gives us:
To Kill a Mockingbird
Lawrence of Arabia
Tom Jones
Irma La Douce
8 1/2
Lilies of the Field
The Manchurian Candidate
The Man Who Shot Liberty Valance

A lot of the themes continue, violating social norms, amorality, illicit sexual behavior are all present. The last two movies listed are about lies and divided men; the stories told about them versus who they are. They are Dick Whitman versus Don Draper movies. I think they are the Apartment and Psycho for next season; they paint a picture of some of the mysteries to be revealed.

In addition, two movies that address racism suggest another possible theme of season 2.