"Imitation of Life" hands down.

The Heart Is a Lonely Hunter (1968)

Although I did not every eventually tear up, I was holding it back the entire time.
~NW~

The Miracle Worker 1962 Surprised that it hasn't been mentioned.

In my experience:
1.
Schindler's List
2.
A Christmas Carol
(the 1951 version in particular)
3.
The Elephant Man
4.
Risen
5.
Amazing Grace
Strangely enough, I don't care for
It's a Wonderful Life
either. And
The Boy in the Striped Pajamas
didn't make me cry; it did shock and horrify me.

Surprisingly I didn't see anybody mention
Sophie's Choice
.

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I'm innocent Madame Nan, I hope you have a soft spot for me.
Exorcist: Christ's power compels you. Cast out, unclean spirit.
Destinata:

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Nan, you're sentimental! Just like me!

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I've actually never seen The Elephant Man. Though I definitely need to. I just really enjoy crying over a movie. Lol
Carrie
Dumbo
Terms of Endearment
Umberto D
Imitation of Life (1959)
Resurrection (1980)
Something for Joey
Humoresque
Gallipoli
Brokeback Mountain
West Side Story
To Sir, With Love
Men Don't Leave
Silverlake Life (doco)
Blade Runner
The Deer Hunter
Now, Voyager

I can't think of 5 but here's mine;

1. Watership Down
2. Elephant Man
3. The Pink Panther Strikes Again ( tears of laughter).

1. Dallas Buyers Club
2. The Normal Heart
3. Titanic
4. Boys Don't Cry
5. American History X
   Now, if you'll excuse me, the father of the atomic bomb wants a saucer of milk.

Surprised no-one has mentioned Shadowlands. I've seen it many times now and it gets me every time.

In no particular order:
*The Elephant Man
*Toy Story 3
*The Green Mile
*Forrest Gump
*Saving Private Ryan
*One Flew Over the Cuckoo's Nest
*Up
*Wall-E
*The Lord of the Rings: The Fellowship of the Ring
*The Lord of the Rings: The Return of the King
*Harry Potter and the Deathly Hallows- Part 2
*2001: A Space Odyssey
*Interstellar
*Inception
Sorry it's more than 5.

Movies that made me cry:
Bambi (sat in cinema and sobbed for ages after the film while my dad tried to explain it was just an animated film)
Original planet of the apes (I was a kid and couldn't believe the young ape died after falling through the roof while spying on some other apes)
Kung Fu Hustle does it to me every time (I love the ending but it kills me for some reasonIt's one of my favorite films)
Elephant man
Old Yeller (saw it as a kid, of course)
The Orphanage (second time I saw it, when I realized how something had happeneddon't want to ruin it for anyone)
Brian's song (again, saw as a kid and bawled)
And probably a few others I don't remember now.

You responded to the wrong post

The Elephant Man
Awakenings
Dying Young
Life is Beautiful
The Life and Times of Grizzly Adams
Cinema Paradisio
Il Postino

The only recent films to make me cry are Brokeback Mountain and Toy Story 3, but I haven't re-watched them so IDK if they are "Impossible movies to not cry on" or not.
Better to be king for a night than schmuck for a lifetime.

When he speaks of his mother and what a terrible disappointment he must have been to her, but all had ever done is try to be good. That bit got me.

Awakenings

1. Dear Zachary(nothing else comes close so here are some other in no particular order)
   Eternal Sunshine, Braveheart, Into the Wild, Moon, Life as a House.

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