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"Old Films" for People Who Want to Watch More "Old Films" but Don't Know Where to Start

A year ago I would constantly tell myself I wanted to get into classic films more, but all my attempts led me to boredom. Thankfully, I got myself out of that mindset, and now the world of cinema is expansive and my options are never limited.
If you're in the same boat as I was a year ago, here's a list of introductory films that will keep you entertained and will (hopefully) open your mind to watching classic films from the 20s, 30s, 40s, 50s, & 60s that are not in this list.
The main function of this is to introduce you to films that are entertaining and will hold your attention. You'll never say "old films" or "black & white" films are boring ever again ((hopefully)) :-)
(This list is a companion to my "documentaries for people who want to watch more documentaries but don't know where to start" list.)
355 users · 2,150 views
 
from letterboxd.com · made by noonelovesme
avg. score: 20 of 51 (39%)
required scores: 1, 6, 15, 23, 32 

How many have you seen?

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1
All About Eve (1950)
All About Eve (1950)
2
Safety Last! (1923)
Safety Last! (1923)
3
Roman Holiday (1953)
Roman Holiday (1953)
4
The Night of the Hunter (1955)
The Night of the Hunter (1955)
5
Sunset Boulevard (1950)
Sunset Boulevard (1950)
6
The Apartment (1960)
The Apartment (1960)
7
North by Northwest (1959)
North by Northwest (1959)
8
The Red Shoes (1948)
The Red Shoes (1948)
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9
Some Like It Hot (1959)
Some Like It Hot (1959)
10
12 Angry Men (1957)
12 Angry Men (1957)
11
Diabolique (1955)
Diabolique (1955)
12
Gentlemen Prefer Blondes (1953)
Gentlemen Prefer Blondes (1953)
13
All That Heaven Allows (1955)
All That Heaven Allows (1955)
14
A Streetcar Named Desire (1951)
A Streetcar Named Desire (1951)
15
It's a Wonderful Life (1946)
It's a Wonderful Life (1946)
16
Laura (1944)
Laura (1944)
17
Double Indemnity (1944)
Double Indemnity (1944)
18
The Philadelphia Story (1940)
The Philadelphia Story (1940)
19
Leave Her to Heaven (1945)
Leave Her to Heaven (1945)
20
Bringing Up Baby (1938)
Bringing Up Baby (1938)
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22
City Lights (1931)
City Lights (1931)
23
Mr. Smith Goes to Washington (1939)
Mr. Smith Goes to Washington (1939)
24
Psycho (1960)
Psycho (1960)
25
What Ever Happened to Baby Jane? (1962)
What Ever Happened to Baby Jane? (1962)
26
Charade (1963)
Charade (1963)
27
Funny Girl (1968)
Funny Girl (1968)
28
Who's Afraid of Virginia Woolf? (1966)
Who's Afraid of Virginia Woolf? (1966)
29
Yesterday, Today and Tomorrow (1963)
Yesterday, Today and Tomorrow (1963)
30
The Children's Hour (1961)
The Children's Hour (1961)
31
The Three Faces of Eve (1957)
The Three Faces of Eve (1957)
32
Funny Face (1957)
Funny Face (1957)
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33
Rebel Without a Cause (1955)
Rebel Without a Cause (1955)
34
On the Waterfront (1954)
On the Waterfront (1954)
35
The Cameraman (1928)
The Cameraman (1928)
36
The Lost Weekend (1945)
The Lost Weekend (1945)
37
Holiday (1938)
Holiday (1938)
38
The Hustler (1961)
The Hustler (1961)
39
Grand Hotel (1932)
Grand Hotel (1932)
40
Rear Window (1954)
Rear Window (1954)
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