In Code Geass, Schneizel and the Chinese eunuchs set up an Arranged Marriage between Crown Prince Odysseus (around 30), and Empress Tianzi (13).
Supplementary materials indicate that, prior to Britannia curbstomping Japan, Genbu Kururugi was considering marrying Nunally (she was 8 at the time), thinking this would deter Britannia from invading. Neither Lelouch nor Suzaku were particularly happy with that idea (Suzaku proposed marrying her instead of his father, but since he was already engaged to his cousin Kaguya, that didn't work out). Lelouch talks Genbu out of it offscreen, apparently offering him top secret information about the Brittanian military in exchange for calling the marriage off.
In the manga Adarshan no Hanayome, Prince Alexid, in his 20s, weds Princess Justinia, age 10, in a political marriage. It's less squicky than it sounds, because he's self imposing a Jail Bait Wait and it is implied that as she grows up he will genuinely fall in love with her.
Seems to be what went on in regards to Ay and Princess Ankhesenamen in Anatolia Story.
Before joining the Runaways, Klara Prast was married off at only 11 years old to an abusive middle-aged alcoholic.
The movie Osama ends with the main character, a female child, getting married off to a man old enough to be her grandfather or even her grandfather's father. The scene right before the last scene is on the wedding day, focusing on how terrified the girl is and how much the other wives hate their husband. The very last scene is at night, showing the old man happy and content, performing the holy cleansing ritual that he had earlier in the movie taught a class of young boys that every good man is supposed to do after he has screwed his wife.
The film Child Bride is about an idealistic teacher campaigning to stop child marriage in her home in the Ozarks. Most of us remember the film more for its infamous skinny-dipping scene involving then twelve-year-old Shirley Mills, who played an eleven-year-old girl who is targeted for this trope by one of the locals.
Deepa Mehta's Water features an eight-year-old girl who was married so young she barely remembers it, has not seen her husband in years, and is now a widow sent to live in an ashram for the rest of her life. Some of the other characters are implied to have been married at least as young, if not widowed quite so early.
The Parent Trap uses this trope as an indirect accusation, delivered with Sugary Malice. When the father tells his daughter that Meredith is about to become part of the family, she surely understands right away that he's talking about marriage. However, she pretends to innocently misunderstand him and gets all ecstatic about how he's finally getting one more daughter by adopting her.
Marianna Ucría is forced to marry her uncle when she is 13.
In The Jewel Of Medina, the Arranged Marriage between the prophet Muhammed (who was in his fifties) and the nine years old girl Aisha is portrayed as the coolest thing ever. The story practically casts her as a young superheroine on team righteous, under the benevolent leadership of her husband. The book subscribes to the theory that they waited a few more years before starting having sex, reducing the squick although not removing it completely. note Which is historically completely wrong, because at the time marriage LAW dictated a couple to consumate their marriage on the first night.
But in 7th century Arabia, such marriages obviously weren't unheard of. Sunni Muslims also still say that Aisha, despite the age difference, really was Muhammed's favorite wife (Shia Muslims tend to look at her in a less positive light though).
When Catelyn finds out that her sister Lysa (teens at the time) was promised to Jon Arryn (early sixties at the time) in a political marriage, she realizes that may be one of the reasons why Lysa's so fucked up.
The Lannisters have one of their younger cousins, the sixteen year old Tyrek, married to a babynote Though there's no suggestion that the marriage was consummated or is intended to be for many years. because she's the last heir of a noble house that they wish to bring under their banners. He gains the mocking nickname "wet nurse". After he disappears and is presumed dead, it's joked that the girl is the only one in the kingdoms to be widowed before she was weaned.
Gender Flipped with Margaery's marriage to King Tommen. This one is actually portrayed as fairly healthy — she's very fond of him and makes a much better maternal influence than his own mother-and-aunt Cersei.
At the start of the series Lord Walder Frey recently married his eighth wife, on his ninetieth birthday. For the record, she's younger than some of his great grandchildren, and pregnant.
Played with in the case of Arianne Martell, who while still unmarried at the time we meet her, has been proposed as a potential bride for a number of men, all of whom are old enough to be her grandfather. She's informed her father that if he wants her to actually marry, he's going to have to find her a husband young enough to still have his own teeth. As it happens, he doesn't want her to marry just yet — but can't tell her why — and is suggesting old men precisely because he knows she'll refuse them.
Didn't stop her from trying to elope with Renly (Two years younger than her), Willas (About the same age), and Edmure (Two years older) and lusting after her uncle Oberyn (18 years older)
Teased relentlessly with Sansa Stark; she begins the books at age 11. Engaged for the first few books to a (psychopathic) boy her own age, it's pretty clear from the beginning that that won't happen. After her engagement to Joffrey is broken, she is forcibly married to Tyrion Lannister (twenty five) at twelve, who refuses to consummate it because she is unwilling and too young. His father demands that he rape the girl to make the marriage legitimate; she's "rescued" by Littlefinger (thirty two), who spends the next book grooming her as his successor (and perhaps more)... and it turns out later that he'd tried to get approval to forcibly marry her as well. Luckily for her, he's now focused on getting her engaged to a dashing fifteen year old squire in line to inherit the Vale. But don't count on it working out for her that easily.
She also has a teased relationship with the twenty-eight year old Sandor Clegane.
Other examples include Fat Walda (18, married to the 40s Roose Bolton), Daenerys (13, to the late 20s-early 30s Drogo and later teased with the 43 year old Jorah when she's 15) and Margaery's first marriage (15, to the 22 year old Renly)
Gender-flipped in Daughter of the Lioness, where regents attempt a political match between the six-year-old king and a fifteen-year-old girl, and later her twelve-year-old sister when the elder elopes with a noble from a neighboring country. The marriage never happens, though.
The Last Days of the Jannissaries, Villain Protagonist Pasha Ali Tepelini is married to a young girl, whom he loves very much. Incidentally, she loves him too, until she discovers that he's being a complete jerkass, and betrays him. She's willing to forgive her husband towards the end though, and is genuinely worried for his safety, when the sultan's assassin shows up to take his head.
In the Honor Harrington novella "Promised Land" (in The Service of the Sword), Ephraim Templeton (55) adds kidnap victim Judith (12) to his collection of wives. That's the least vile thing he does. It comes back to bite him hard by the end.
Subverted in The Chronicles of Narnia, where Tomboy Princess Aravis Tarkheena is betrothed to an older man...but she escapes on time, and eventually marries someone her age that she comes to truly love. Aravis's case wasn't helped by how a) her prospect older husband Ahoshta is the local Smug Snake as well as a Gonk; b) the marriage was arranged upon suggestion of Aravis's much hated Wicked Stepmother.
Aravis's best friend Lasaraleen, however, goes through with her Arranged Marriage and doesn't seem to understand why Aravis wouldn't want to. However, she's sort of a Lovable Alpha Bitch more concerned with her husband's money and position. And we actually don't know how old her husband is; for all we care he could be either a super old dude or a man as much in his twenties. We do know he talks to her - she's always quoting him - and indications are they are both happy with their match.
In Crime and Punishment, Svidrigrailov, a man in his 60s, gets engaged to a 14-year-old girl. Although it wasn't too unusual for people to get married that young back then, such a huge age difference definitely was, and the whole thing is very much played as Squicky. Even Svidrigrailov himself seems to realise it, as afterwards he has a dream in which a five-year-old girl attempts to seduce him, which thoroughly creeps him out, and soon after he commits suicide.
The Wife of Bath from Canterbury Tales was first married to an old man when she was twelve years old. Notably she is so pleased with the arrangement - indulgent, manipulable old man, short marriage, and wealthy widowhood - that she goes on to willingly marry three other 'good old men'.
15-year-old Kaede from Tales of the Otori is first engaged to a man who dies of old age before they are even officially married.
In Warbreaker, teenaged Siri is sent off to marry the God King Susebron, who is over half a century older, even though his godhood makes him look like a young man in his twenties. Fortunately for her, he turns out to have no idea how sex works, so they don't end up consummating the marriage until after she's grown to love him.
Gender-flipped and downplayed in A Brother's Price, where the boys are married at sixteen to whole families of sisters, the oldest of them tend to be his senior. Of course, the brides aren't really old (the have to get married before they hit menopause, after all); they tend to be in they twenties and the boy is a teen - an age difference, with the genders swapped, no-one reading, say, Jane Austen's novel would bat an eye for. But all of the implications of this trope still follow: a young groom is put at mercy of his adult spouses, he's considered their property and there's a need for offspring, so Marital Rape License is at play. Or even Marital Gang Rape License, if you will. The trope is played straight (age-wise) when Kij Porter - presumably in her late-thirties, old enough to be his mother - takes an interest in the not-quite sixteen years old Jerin and wants to 'sample' her potential husband. Jerin is understandably horrified.
Also in this world, when a man marries, he marries all the sisters in the family, even the ones who aren't yet conceived when their husband marries into the family. It's quite possible for a husband to be old enough to be his wife's father in this setting, as well as the inverse.
Live Action TV
Law & Order: SVU had a case along these lines. The marriage was not legally binding, but it was treated as a real marriage by the cultists.
It also produced a pregnancy, which is what kickstarted the whole episode, when the child was checked into a hospital.
Not "old" per se, but in season one of Blackadder, Prince Edmund marries the 8-year old Princess Leia of Hungary, much to his own dismay. Subverted somewhat as the marriage is purely political and completely platonic, with Leia even serving as something of a Morality Pet for Edmund. They spend their wedding night with Edmund reading her a bedtime story.
In the Police Squad! episode "Testimony of Evil" (a.k.a. "Dead Men Don't Laugh"), Ed Hocken describes a man as "Married, one child. That didn't work out so he married a grown woman."
Series 1 of Big Love introduces us to Rhonda, the 16 year-old girl promised to fundamentalist Mormon prophet Roman Grant; the marriage doesn't go ahead, but such marriages are presented as common on the Juniper Creek compound. Later in series 3, Nicki manages to prevent her 14 year-old daughter Cara Lynn from being married off to a much older man.
In "I, Claudius", the empress is apalled that young men are not bothering to get married and orders that there better be some marriages soon. She then warns them that there better not be any engagements to children just so they can put of marrying them for a decade.
In the Criminal Minds episode "Minimal Loss", cult leader Benjamin Cyrus (played by Luke Perry) marries a 15-year-old girl, and has his way with whatever woman he wants in the cult, as per his own decree.
In Doctor Who, teenager Ping-Cho was set to marry an old man she'd never met. Although she's resigned herself to it, she's quite relieved when he dies.
Blutengels song "Black Wedding" can be interpreted this way.
Rod Stewart's "Tonight's The Night (Gonna Be Alright)" has also been interpreted as an older man coming on to a teen-aged girl ... and wanting to consumate something more than just a sexual relationship.
In Fiddler on the Roof, Tzeitel is placed in an arranged marriage to Lazar Wolf, who's actually older than her own father. She mocks this in the song "Matchmaker, Matchmaker," which implies this arrangement is common from the matchmaker of the village.
Mitsuru Kirijou's Social Link in Persona 3 involves the board of directors arranging for her to marry a much older man (She's about to graduate from high school, he's at least in his thirties) to stabilize the Kirijo Group after her father's death.
In Suikoden the vampire Neclord makes a habit of abducting young women to make them his bride. After building his castle near the Warriors Village he visits said location and demands a new bride every year.
In one Chick Tract called "The Little Bride", the marriage between Aisha and Muhammed is used to condemn Islam, highlighting that she was only 6 when they got engaged and only 9 when they got married. The tract draws the conclusion that Muhammed was a pedophile rapist.
Weg from Fairy Dust has no tastes for children, but bought two eight and six years old wives for political gain.