The phrase is often used in order to indicate a really upsetting past, and it usually will imply in such a case that it was something the person did repeatedly. Less often do you see anyone actually cry themselves to sleep. If this is shown, it's also likely that the character doing it is The Woobie.
- In GO-GO Tamagotchi! episode 33, Lovesoratchi is sad that he can't go out to space with Mofumotchi, goes to his room, and cries on his bed while looking at a picture he drew of a rocket ship. When Lovelitchi and Melodytchi check on him later, he's sleeping and still has tears in his eyes.
- In K-On! season 2 episode 20, after the school festival, the members of Afterschool Tea Time break down crying in realization that the show they just played would be their last performance together before the four senior members graduate. When Sawako goes up to the club room to meet up with them, she finds them all asleep.
- Pokémon Adventures: When her Ratatta "Ratty" evolves into a Raticate, Yellow (who has no idea what evolution is) is so distraught by the changes that she begins hysterically crying to the point where she ends up falling asleep with tears in her eyes, something that Blue comments on. She's apologetic the next day, though.
- In Yuri!!! on Ice episode two, after being rejected by Yuri, Victor is seen hugging his dog Makkachin with tears in his (closed) eyes as they sleep.
- In a Superman comic called "The Unknown Super Deeds", Superboy surmises as he picks up a boy who fell into a well that he cried himself to sleep while Superboy was getting there.
- A variation is discussed in a one-shot story of The Simpsons. After Springfield is cut in two (likely a Mythology Gag from the episode A Tale of Two Springfields"), Bart laments that Milhouse is stuck on the other side of the wall splitting the town. Homer tries to console him with a story where another little boy was sad to be away from his friend, which ends with the boy crying himself to death. Bart says Homer is "not much a father," but Homer doesn't mind.
- Bridge to Terabithia 2: The Last Time: After Jess and Leslie see each other for the first time in five years, the latter having been thought to be dead (she was actually a recently-rescued victim from a Human Trafficking ring, after being abducted five years earlier and assumed to have drowned as a child), Leslie ends up breaking into tears while in Jess' arms, and fell asleep after crying for several minutes.
- Mentioned in chapter 2 of Harry Potter: the Other Child (a Wrong Boy Who Lived fic, with Harry naturally neglected in favor of his brother).
- In the Empath: The Luckiest Smurf story "Smurfed Behind: Smurfing In Heaven", Empath cries himself to sleep after voicing his desire to kill himself after avenging his fellow Smurfs of their (supposed) deaths at the hands of the Schliphargons.
- In Lincoln is Done, Luna Loud cries herself to sleep due to missing her runaway brother Lincoln and feeling guilty because he was mad and that's why he ran away.
- In Soldier of Zero, Louise keeps a stock of dreamless sleep potions that she used to use as an alternative to crying herself to sleep.
- Evershade: As said at the beginning of Chapter 6, when dealing with the shock of having a Gender Bender:
The next morning, I slowly regained consciousness, greeted by the feeling of a wet pillow against my face. I wondered for a moment why it was wet in the first place, and finally remembered why.
I cried myself to sleep that night.
- Ships Ahoy!: When Olive finds out about Oscar deliberately wishing to become a Lab Director and witnesses him being promoted to the position, she breaks down in the ball pit and begins crying, cycling through a range of thoughts that eventually leave her drowsy enough to fall asleep and not wake up until everyone has left work for the day.
- Vow of Nudity: Spectra does this in her origin story, after one of her clients calls her a disgrace to her heritage for living openly among humans as a changeling, disregarding that she has little choice thanks to her curse. The narration suggests most of her nights end like this, due to how poorly her employer and the other townsfolk treat her.
- At the ending of All Dogs Go to Heaven when Charlie's ghost comes to say goodbye to Anne-Marie, he sees his friend Itchy sleeping next to her with a very sad, furrowed brow, implying that he cried himself to sleep after seeing Charlie drown.
- In An American Tail, Fievel cries himself to sleep after giving up on finding his lost family and taking up residence in a dark, rainy alley.
- Coraline: After her parents disappear, Coraline makes makeshift dummies of them on their bed and climbs in to sleep next to them. As she cries, the scene transitions to her already sleeping.
- In Shrek Forever After, Rumpelstiltskin gives Shrek a deal that he could become intimidating again for a day, but a day needs to be taken from his life in exchange. Rumpelstiltskin tricks Shrek into letting him take his birthday, which leads to, among other things, not having met Princess Fiona so she escaped the Dragon's Keep on her own. While telling Shrek off, Alternate Fiona says, "Did you cry yourself to sleep every night?!".
- In Turning Red, Mei cries herself to sleep after the first day of dealing with her giant red panda form.
- Josh cries himself to sleep on his first night as Tom Hanks in Big, and no wonder. Nobody knows who he is, he's staying in a fleabag hotel in the Big Rotten Apple, somebody just got shot outside, and another guest is shouting verbal abuse.
- In Mrs. Doubtfire, Miranda confides to the titular character that when she was married, she was so unhappy with her married life that she would cry herself to sleep. For context, Mrs. Doubtfire is her ex-husband, in a very convincing disguise. Ouch.
- Ender's Shadow
- During his first night at the Battle School, Bean overhears a kid crying himself to sleep. Bean, who at this point is an extreme rationalist, dismisses the kid as stupid because crying won't fix the situation. Having grown up on the streets, Bean had no parents and thus is extremely emotionally stunted due to having to fight for survival every day of his life.
- Of course, thinking along these lines leads him to ponder the important people in his own life. Poke, the first person who showed him kindness, who gave him a chance, who saved his life, was murdered, and deep down he knows she sacrificed herself to protect him. He doesn't understand why she did all that, but he still misses her.
He wiped his eyes, rolled over, and willed his body to relax and go to sleep. [...] Long before morning his pillow would be dry.
- In The Girl The Dog And The Writer In Provence, the titular girl Freja sometimes falls asleep sobbing because she misses her mother Clementine and is worried because Clementine is ill.
- Heralds of Valdemar:
- In Intrigues, when Mags is driven from the Collegium due to psychic pressures and depression, he cries himself to sleep at least once.
- In By the Sword, Kerowyn does it after leaving the man she loves and returning to the Skybolts. Being The Stoic, she's actually somewhat proud of herself for crying so quietly that her tentmates don't know she's doing it.
- In Mansfield Park, little Fanny cries herself to sleep every night after she gets adopted by her wealthy relatives because she misses her family and nobody is particularly kind to her. After a week, her cousin Edmund finds her crying and comforts her. Since then she's calmer and happier.
"The little girl who was spoken of in the drawing-room when she left it at night as seeming so desirably sensible of her peculiar good fortune, ended every day's sorrows by sobbing herself to sleep."
- In My Side of the Mountain Sam Gribley's first night living off the land in the New York Catskills doesn't go as well as he had hoped:
(After describing the winds going through the valley right to where he was, the cold wet ground, and the sound of a bird keeping him awake) Well, anyway, the whole night went light that. I don't think I slept fifteen minutes, and I was so scared and tired that my throat was dry. I wanted a drink but didn't dare go near the stream for fear of making a misstep and falling in and getting wet. So I sat tight and shivered and shook—and now I am able to say—I cried a little tiny bit. Fortunately, the sun has a wonderfully glorious habit of rising every morning.
- Realm of the Elderlings. In The Liveship Traders, Brashen Trell remembers how he did this on his first sea-voyage after being disinherited and discovering the brutal hardships of being a sailor. Then, another sailor tried to molest him.
- In Suicide Notes From Beautiful Girls, Chapter 26 opens with June crying herself to sleep, then going to school the next morning with red, puffy eyes.
- The Time Traveler in The Time Machine is so distraught when he discovers his machine is missing, leaving him trapped in the distant future, that he falls and cries until he wakes up the next morning.
- Mentioned in one chapter of Dave Barry's Complete Guide to Guys, in a chapter where he explains the unbridgeable distance between men and women's thought processes: Eileen offhandedly mentions they've been dating for six months, sees Roger lost in thought and makes a bunch of assumptions (Am I being too forward with this? Does he really want the same thing out of this relationship as I do? Oh no, he's getting angry at me for all this, I've ruined everything!), building up from them regarding their relationship and ends up crying herself to sleep after a conference call with all her friends because she thinks she's being a horrible person to Roger. Roger, on the other hand, was lost in thought because he remembered it'd been at least six months since he'd gotten the car checked, was getting angry because he was imagining how much the machanics were going to charge, and of course has no idea what Eileen is getting upset over in the first place.
- In the first book of the Venus Prime series, Sparta often cries herself to sleep during the months that she spends training to become a Space Board Inspector because the training is brutal and she is incredibly isolated.
- The preadolescent heroine of the Goosebumps book "The Ghost Next Door" does this when she discovers she's already dead.
- Ascendance of a Bookworm: The setting's noble society is very big on Emotion Suppression, but people past a certain age have a Secret Room that partly functions as a place in which to properly sort out their feelings. Rozemyne happens to be alone in hers when a letter she's reading makes her cry because her means of exchanging letters with her commoner birth family was suddenly cut off and she's reading the very last letter from her family that made it to her before it happend. Next thing she knows, she's waking up sprawled on the table at which she had been sitting.
- In The Mer, Val drowns in the ocean and is transformed into a Mer, a being that can't live on land. She's told that she must never contact her family again because They Would Cut You Up. That night she cries herself to sleep, her tears dissolving into the water.
- John's Lily: After Lily is kidnapped for the second time, she cries herself to sleep in the filthy room in the back of the public-house where her kidnappers are staying.
- In Shock Point, Cassie cries herself to sleep every night at the abusive reform school Peaceful Cove. She makes sure to do it quietly so she won't get in trouble.
- In the Friends episode "The One With Phoebe's Rats" Ross and Rachel hire an attractive nanny. In front of Rachel, Ross has to pretend that the nanny isn't hot, but once Rachel leaves he admits that she's "so hot I cried myself to sleep last night."
- In the Starsky & Hutch episode "Little Girl Lost," Hutch takes in a recently-orphaned twelve-year-old girl so she won't have to spend Christmas in Juvie. For most of the day she acts tough and angry and doesn't show any weakness, but that night she cries herself to sleep while Hutch listens from the next room, unable to help her.
- Star Trek: Deep Space Nine: Jadzia Dax talks about how she had some bad times while training to host The Symbiote, one of them being crying herself to sleep.
- Star Trek: Picard: In "The Impossible Box", Raffi has a tear streaming from the side of her right eye when Rios tucks her into bed, and she dozes off soon afterwards.
- In The Twilight Zone (1959) episode "Two", the woman cries herself to sleep after her hostility, left over from pre-apocalyptic days, has driven off the only other person on Earth.
- The song "Don't Laugh at Me" by Mark Willis, which about how kids that get bullied feel, contains the line "And I know how it feels to cry myself to sleep...".
- From Kirsty MacColl's song "England 2, Columbia 0":
So I got into a taxi and sobbed all the way home
Called my friend up in Sao Paulo and cried down the phone
I played some tragic music and I lay down to die
But later I awoke and I hadn't stopped crying
- In Life: the Game, if you reject one of the OK girls (i.e. the girls who are neither psychopaths nor old ladies), it will say that you greatly regretted rejecting her and cried yourself to sleep two days of the week.
- Pokémon: Whismur is prone to startle itself with the sound of its own crying, causing it to cry EVEN LOUDER, until it tires itself out and falls asleep.
- Brought up in complete irony in Jo Jos Bizarre Adventure Abridged, when Jonathan completely denies getting completely beaten by Dio, being abandoned by his friends, and crying himself to sleep that night. As in the source material, it is meant to show the drastic turnaround Jonathan's life has taken now that Dio is part of the family.
- Implied in the Adventure Time episode "Crystals Have Power" when Finn states "You didn't even make me cry silently into my pillow last night for thirty minutes."
- A variation from South Park:
Blaneologist: I can show you how to make your true self appear. Let me ask you all something: do you consider yourselves to be happy?Butters: I don't think I'm very happy. I always fall asleep to the sound of my own screams.Blaineologist: [pause] Right. See, the reason that you are...
- In an episode of The Simpsons, after the family goes visit the girl in juvenile hall that Bart befriended to treat her to a Mexican diner, the prison warden talks about his upcoming evening.
Warden: Well, my shift's over. I guess it's back to my bachelor apartment, make a tuna sandwich, turn on Will and Grace, and cry myself to sleep...Marge: Mhh... would you like to join us?Warden: (Angrily) Didn't you hear me? I have an evening planned!