Bastion.

Movies: The Green Mile, the beginning of Up (the montage set to Ellie's theme) and Toy Story 3 (OUR FRIENDSHIP WILL NEVER DIE-- song abruptly ends), and I felt a tear welling up towards the end of Seeking A Friend For The End Of The World.

TV: Futurama gets me in the feels quite a bit, specifically with Jurassic Bark, the last few minutes of the episode where Fry trades hands with the Robot Devil, and the montage of Fry and Leela growing old together at the end of Meanwhile...

Games: The ending of Bastion, To the Moon, Walking Dead Season 1, Beyond Good & Evil (the part on the moon involving Pey'j), bits and pieces throughout Ghost Trick, the last trial from Phoenix Wright: Justice For All (the first time you see Phoenix's head down sprite) and the last two trials from Trials and Tribulations, and I teared up a bit at the part in GTA IV where I decided the deserter's fate (I actually paced back and forth, in game, for several minutes, deciding what to do.)

Madoka (it's an anime series but like... stuff I watched recently)
Ending of the Legend of Korra

i only ever tear up, but still.
Elysia: Mommy? Why are they putting all that dirt on Daddy?
Gracia: They're burying him, dear.
Elysia: But if Daddy gets buried, then he won't be able to do all his work.
Gracia: [crying] Elysia!
Elysia: Daddy said he has a bunch of work he needs to do! No, stop it! Stop putting dirt on him! Daddy!
and the death of ACE

Game: Crisis Core FFVII. Just listen to The Price Of Freedom from the OST. MGS3 ending too.
Movie: Hachiko

The Dog of Flanders (animation)
Grave of the Fireflies (also animation)
Final Fantasy: The Spirit Within

Boku no Pico

when i say something like that i'm usually exaggerating, so im gonna assume this is the same case as i never witness anyone crying while watching a movie, though i've seen people making out while watching 12 years slave.
movies:
Come and See - the only war movie that almost makes me cry, and always makes me feel sick.
Millennium Actress - not just this one in particular, satoshi kon´s characters are usually obsessive fans, i can relate with that, it makes me feel at home
All About Lily Chou-Chou - being the weird kid in highschool that only had a couple of friends and kept to himself most of the time i too found comfort in music.
The Elephant Man - John Hurt is so good in here he almost makes me cry
The Secret of NIMH - its a heavy movie for kids in a lot of aspects, i dont think i´ll ever forget it
Whisper of the Heart - i was younger, around that age when you start questioning what you want to do with your life, and seeing how the parents where always so comprehensive with the main character even though they knew the road she chose would be more difficult always got me, mostly because i've never been given that chance.

Movies : Marley & Me, The Terminator 2

Games : The Walking Dead (Both Seasons)

Movies: Too many to list
Games: To The Moon, Final Fantasy X (ending), Final Fantasy XIII-2 (ending), Final Fantasy VI (Terra and Cid). There's more but I can't think of them right now.

I didn't cry but Hachiko and Earthlings made me extremely sad.

Movie - Platoon (When Green Goblin gets shot up it breaks my heart).
Game - Mass Effect 3 when Dr. Mordin dies.

To the Moon - teared up throughout the whole game ;;
Girl with a Heart of (on Desura) - Dying mother ;;

Up - sobbed at the backstory, what a good way to start a movie ;~;
Brave - the broken relationship between the mother/daughter
Pretty much every Studio Ghibli movie (Grave of the Fireflies, Porco Rosso, Princess Mononoke, Spirited Away, My Neighbor Totoro, etc.)

One Million Dollar Baby - cried so much after the ending ;~;
And countless romantic movies lol

Games: The Walking Dead (Season 1), The Last of Us, Beyond: Two Souls
Shows: Game of Thrones (you know what epiosode I'm referring to.), Hannibal (Season 2 Finale), Teen Wolf (Season 3 Ep. 23), Doctor Who (The Time of the Doctor)

I know there's more but can't think of any off the top of my head. I get attached to characters REALLY easy so their deaths always hit me pretty hard. Game of Thrones was the one I've cried the most at, I bawled for literally 30 minutes and was shaking even tho I was expecting it. shakes fist at every writer that kills off my favourite characters

Can't remember any movie, but the 2 latest games that almost brought me to tears were both Bioshock 2 (best possible ending, little sisters are freed and Eleanor is happy, but Delta dies) and Infinite

I am not a real big Naruto fan I used to like it, I have never watched all episodes, just random ones.
But I must say that it was really touching the ending of the battle of the two Uchiha brothers against Kabuto, when Itachi reveals to Sasuke all the truth about the whole murder, that did make me tear.

I think the one movie that made me cry the most was Hachi, dog's tale. Also Mary and Max, that movie was beautiful and not a simple tear jerker like Hachi was.

Games... Portal 2... Bastion was beautiful can't remember if I cried but goddamn that ending... Little inferno... Braid made me really fucking sad... Machinarium...

If you wanna cry all day just watch Hachi or Clannad if you feel like watching an anime.

Also Eminem. Fuck. His "when I'm gone" made me cry just by listening to it the first time and same with Stan. They still do every now and then.

Prince of Persia series. It wasn't that the story was sad, it was just that frustrating at times....

All movies i cried were mentioned already, only other one would be Men of Honor (the begning, the scenes with his father). Theres a special case that made me cry way more then i ever cried- but im failing to remember what movie was it (kinda drunk right now).

I hadn't cried with any game (only feeling strong emotions) BUT i did cried with Fallout's Intro(the first one), when i fired it up 'once again' many years after my first playtrougth. It was shortly after the revealing of Fallout 3 trailer/intro, and after re-watching fallout 2 and 1 intro's and songs. I guess nostalgia played strongly, but it was mainly because of the lore and that song (in context). Crap, im almost crying again.

That and Kara, the tech demo.

PS: just came back to mention that because of the above im reinstalling fallout again. If i remember the other movie i will come back here.

I cried when ghost died in call of duty modern warfare 2..

The only game I remember crying over was The Legend of Zelda: Twilight Princess.
I was also very teary during the Dragon's Keep expansion for Borderlands 2. But those were tears of laughter, not sadness.

There's been a handful of movies, but the only ones I can remember shedding tears for, because I just rewatched them recently, were Mewtwo Strikes Back, and The Power of One.

Movies: 12 Years a Slave, Glory, Saving Private Ryan, The Book Thief, Princess Mononoke, Moulin Rouge.
Books: The Old Man and the Sea, All Quiet on the Western Front.
Games: none, yet.

Not necessarily cried but made me sad

To the moon, Papo and Yo, Deadlight, Gone Home(since you're ok with a movie, highly recommend it), Bastion and Limbo

Movies - The Champ, Bambi (both watched as a child)
Games - To The Moon