Many of the most compelling love stories are tragic ones. From Romeo and Juliet to Ennis and Jack, here’s a look at nine romances that have had the opposite of happy endings. How many have left you in tears?

Anna Karenina

Anna Karenina appears to have the perfect happy family with her husband, a wealthybureaucrat, and their son, until she begins what becomes a very public affair with a handsome count. Their relationship quickly dissolves, along with her place in society. Disgraced, shamed, and heartbroken, Anna meets her death on the Russian railroad.

West Side Story

In thismusical adaptation ofRomeo & Juliet set in 1950sNew York City, the love of teenagers Maria and Tony is doomed by their affiliations with rival gangs. They carry on a secretromance as tension between the gangs escalates and ends intragedy.

Madame Bovary

InGustave Flaubert’snovel,Emma Bovary is bored and dissatisfied with her marriage to a country doctor. Her escapes into fantasy and infidelity lead her to financial ruin and, ultimately, a tragic end.

Brokeback Mountain

In E.Annie Proulx’sshort story, which later became an Academy Award-winning film, ranch hands Ennis and Jack fall for each other in rural Wyoming and begin a long-term love affair. An unacceptingculture compels them to keep their love secret, however, and they live apart while each secretly pines for the man he truly loves.

The Hunchback of Notre Dame

The Hunchback of Notre Dame isVictor Hugo’s tale of the unrequited love of hunchbacked bell ringer Quasimodo for the beautiful, kind-hearted street performer Esmeralda. When Esmeralda’s jealous stalker stabs the man with whom she is trysting, she is blamed for the crime and eventually hangs. Years later, the skeleton of a hunchback is found embracing her skeleton in its tomb.

Wuthering Heights

Emily Brontë’sWuthering Heights is among the most dramaticromantic tragedies inliterature. Societal constraints and personal pride prevent Cathy from being with Heathcliff, and she eventually marries another man. Heathcliff, heartbroken, remains bitter through the rest of his life, which he commits to seeking revenge on the forces that kept him apart from Cathy. When she dies in childbirth, he directs his fury at her remaining family (as well as his own).

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Titanic

InJames Cameron’s1997 film, upper-class Rose meets working-class Jack aboard theTitanic. Jack offers analternative to Rose’s fiancé, with whom she is not in love, and her sheltered life, which bores her. Their plans to run away together are thwarted when the ship sinks following a collision with an iceberg. While Jack perishes in the icy waters of the Atlantic, Rose goes on to live a long, rich life influenced by her brief time with Jack.

Romeo & Juliet

The love ofRomeo and Juliet,Shakespeare’s star-crossed lovers, is doomed by their feuding families. The two fall in love at first sight and secretly marry but are prevented from being together for fear of their families’ disapproval. Seeking a way to be together, Juliet fakes her own death, with devastating consequences.Romeo & Juliet is the quintessential tragic love story, as evidenced by its countless stagings and numerous filmadaptations.

Tristan and Isolde

One of the classic romances ofWestern literature,Tristan & Isolde is the tale of a princess who, pledged to marry a king, instead becomes involved with his nephew, Tristan. The two are, of course, eventually separated and years of pining ensue; the story culminates in a thwarted reunion. Originally a 12th-centurylegend, the story has been adapted countless times, most notably asRichard Wagner’s operaTristan und Isolde.