If you're looking for anime similar to The Villainess Turns the Hourglass (Novel), you might like these titles.
Jill is sentenced to death by the crown prince, her fiancé. But just before she dies, she’s sent back in time six years to the party where their engagement had been decided. To avoid this route of ruin, Jill immediately proposes to the person standing behind her…but it’s the man who was her greatest enemy, Emperor Hadis?! Jill knows all about his future descent into evil. She quickly retracts the proposal, but the delighted Hadis takes her back to his castle and makes her a meal. Completely won over by the food, Jill makes a life-changing decision… “I’m going to reform—no, I’m going to make you happy!” It’s time to redo this life with the enemy!
Rishe, the duke’s daughter, is no stranger to reincarnation—it’s her seventh life, after all. Each life restarts at her broken engagement. Having been a merchant, a maid, and a knight, she now desires leisure. But her world changes when a prince, who killed her in a past life, proposes! To prevent war and live to a ripe old age, she begins her seventh life as the bride of an enemy nation’s prince.
One day, Crown Prince Sieg hears the Voices of the Gods out of the blue. Apparently, his fiancée Lieselotte is a “tsun de rais” villainess destined to meet her demise...and her sharp tongue is just a way of covering up her embarrassment. The prince can hardly contain himself after discovering Lieselotte's adorable hidden side. Little does he know, the heavenly beings that bestowed this knowledge unto him are actually high schoolers! Can he use their divine prophecy (let's play commentary) to save his betrothed and avoid a Bad End?!
Alicia is a girl that hates "goody-two-shoes" heroines. Her wishes come true when she is reincarnated into a villainess in her favorite otome games. She strives to be the world's most evil villainess in history. However, the more she tries to be a villainess, the more the prince appears to like her...
Unaired episode bundled with the 7th volume of the My Next Life as a Villainess: All Routes Lead to Doom! manga.
The world turns upside down when a corporate drone wakes up as Rae Taylor, the heroine in her favorite otome game, Revolution. Rae is elated at the opportunity to court Claire François, the game’s villainess and the object of her affection. Armed with her knowledge of the game and events to come, Rae sets out to make Claire fall for her. But how will the villainess take Rae’s romantic advances?
Wealthy heiress Catarina Claes is hit in the head with a rock and recovers the memories of her past life. It turns out the world she lives in is the world of the game Fortune Lover, an otome game she was obsessed with in her past life... but she's been cast as the villain character who tries to foil the protagonist's romances! The best ending the game has for Catarina is exile, and the worst, death! She'll have to find a way to avoid triggering the flags of doom, and make her own happy future! The misunderstanding-based screwball love comedy now begins!
The villain Ling Chen has a history of hate and violence with the hero, Ye Zimu. Out of nowhere, a reset triggered Ling Chen to return to when he was 17 years old! He has a chance to stop the hero in his path, before Ye Zimu grows to become his worst enemy...
Best boss ever, prodigy of the business world, genius creator, visionary of the century. These are the descriptions used for Pei Qian, President of Tengda Corporation. Ever since his rebirth, Pei Qian finds himself in possession of a system that rewards him if he manages to lose money. Instantly, a brilliant idea comes to mind — making crappy games!
When her engagement to the prince ends unceremoniously, details of the young noblewoman Aileen’s past life come rushing back and help her realize she’s living inside the world of one of her favorite otome games—as the heroine’s greatest rival! However, her memory has more plot holes than bad fan fiction… and the only certainty is that if she doesn’t do something quick, her death is all but assured. The hero/main-love-interest can’t be relied on, so why not see what the last boss has to say?