It is an ending so epic that Shakespeare himself couldn’t better it. In the golden city of Alexandria, Cleopatra VII (69-30 BC), Queen of Egypt, holes up in her self-made mausoleum, as her arch-nemesis Octavian (later known as Augustus), Emperor of Rome, closes in. But she is not alone. In her arms is her lover, the Roman general and statesman Mark Antony (83 -30 BC), who is dying of a self-inflicted stab wound. As he slowly slips away Cleopatra wails, beating her chest, smearing herself in his blood. Usually, a master of self-possession, she is losing her mind. Antony dies as Cleopatra holds him. She will soon follow him to the grave.

Antony first met Cleopatra when she was ‘still a girl and inexperienced’

Their love story had started over 10 years earlier when both were in their prime. Cleopatra was the divine Ptolemaic ruler of prosperous Egypt – brilliant, silver-tongued, charming, scholarly and the richest person in the Mediterranean. Politician and soldier Antony, supposedly descended from Hercules, was “broad-shouldered, bull-necked, ridiculously handsome, with a thick head of curls and aquiline features.”

Boisterous, mirthful, moody and lustful, Antony had been a favorite of Caesar. In the wake of Caesar’s assassination, Antony formed an uneasy Triumvirate in 43 BC with Marcus Aemilius Lepidus and Caesar’s nephew Octavian to rule the sprawling Roman Republic. Antony was put in charge of the Empire’s rowdy Eastern territories.

In 41 BC, Antony sent for Cleopatra while he was staying in the magnificent city of Tarsus, near the coast of what is now Turkey. He had first met Cleopatra in Rome when she had been the young mistress of his mentor Caesar (the two had a son Caesarion). But Antony was meeting a very evolved Cleopatra. Caesar “had known her when she was still a girl and inexperienced in affairs,” the Greek writer and philosopher Plutarch wrote, “but she was going to visit Antony at the very time when women have the most brilliant beauty and are at the acme of intellectual power.”

Cleopatra wooed Antony 10 years later, making him lose ‘his head to her like a young man’

Aware of Antony’s love of spectacle – and of Rome’s interest in her riches – Cleopatra orchestrated an entrance into Tarsus designed to awe Antony and his cohorts. According to Stacy Shiff’s Cleopatra: A Life, she sailed into the city in an “explosion of color” underneath billowing purple sails:

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She reclined beneath a gold-spangled canopy, dressed as Venus in a painting, while beautiful young boys, like painted Cupids, stood at her sides and fanned her. Her fairest maids were likewise dressed as sea nymphs and graces, some steering at the rudder, some working at the ropes. Wondrous odors from countless incense-offerings diffused themselves along the river-banks.

The pageantry worked. “The moment he saw her, Antony lost his head to her like a young man,” he Greek historian Appian wrote. Cleopatra was not done – throwing extravagant parties and dinners for the Romans, flaunting her riches by giving away all the furniture, jewels and hangings from the soirees. She drank and sparred with Antony, who “was ambitious to surpass her in splendor and elegance,” throwing his own parties that never quite lived up to hers.

Though it appears their attraction was genuine, it was also politically savvy “and…thought to harmonize well with the matters at hand.” As Schiff notes, Antony needed Cleopatra to fund his military endeavors in the East and Cleopatra needed him for protection, to expand her power and assert the rights of her son Caesarion, Caesar’s true heir.

The powerful rulers had a playful relationship

Antony soon followed Cleopatra to Alexandria, which was experiencing an artistic, cultural and scholarly renaissance under their Queen. The two powerful rulers often behaved like college students, forming a drinking society they called the Society of the Inimitable Livers. “The members entertained one another daily in turn, with an extravagance of expenditure beyond measure or belief,” Plutarch explained.

The new couple also loved to tease each other. One legend has it that at one party, Cleopatra bet Antony she could spend 10 million sesterces on one banquet. According to the Roman chronicler Pliny the Elder:

She ordered the second course to be served. In accordance with previous instructions, the servants placed in front of her only a single vessel containing vinegar. She took one earing off, and dropped the pearl in the vinegar, and when it wasted away, she swallowed it.

Another time, Antony, the masterful athletic soldier, was frustrated as he fumbled with a fishing rod during a riparian entertainment. “Leave the fishing rod, General, to us,” Cleopatra joked. “Your prey are cities, kingdoms and continents.”

The Death of Cleopatra, 1785

The Death of Cleopatra, 1785
Photo: Fine Art Images/Heritage Images/Getty Images

Antony left a pregnant Cleopatra to go to Rome, married another woman, but they eventually reunited

Antony was soon off to Rome to report on his triumphs. In his absence – by 40 BC –Cleopatra gave birth to their twins, Alexander Helios and Cleopatra Selene. That same year Antony married another intelligent dynamo – Octavian’s sister Octavia. Seemingly happy in his new marriage, Antony and Cleopatra did not meet for three and a half years, until the lovers reunited in Antioch, the capital of Syria in 37 BC.

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The two picked up right where they left off, even issuing currency engraved with both their faces. In Antioch, Antony met his twins for the first time and bestowed large swaths of land on their mother. “As of 37, Cleopatra ruled over nearly the entire eastern Mediterranean coast, from what is today eastern Libya, in Africa, north through Israel, Lebanon, and Syria, to southern Turkey, excepting only slivers of Judaea,” Schiff writes.

For the next two years, the couple would often travel together, as Antony’s military and administrative exploits took them all over the Mediterranean. It was during this period that Antony’s military prowess began to falter, causing him to lose thousands of men. Of course, instead of the blame being placed on Antony’s rash, bull-headed decisions, Plutarch would blame the failures on Cleopatra:

So eager was he to spend the winter with her that he began the war before the proper time and managed everything confusedly. He was not master of his own faculties, but, as if he were under the influence of certain drugs or of magic rites, was ever looking eagerly towards her, and thinking more of his speedy return than of conquering the enemy.

The couple staged ‘The Donations of Alexandria’ against Octavian

However, Antony’s fortunes were briefly reversed when he successfully conquered the kingdom of Armenia. In the fall of 34 BC, he triumphantly returned to Alexandria, where the Armenian royal family was paraded in chains. Reunited with Cleopatra, “the two most magnificent people in the world” staged an event that came to be known as “The Donations of Alexandria.” According to Schiff:

In the open court of the complex that fall day the Alexandrians discovered another silver platform, on which stood two massive golden thrones. Mark Antony occupied one. Addressing her as the “New Isis,” he invited Cleopatra to join him on the other. She appeared in the full regalia of that goddess, a pleated, lustrously striped chiton, its fringed edge reaching to her ankles. On her head she may have worn a traditional tripartite crown or one of cobras with a vulture cap. By one account Antony dressed as Dionysus, in a gold-embroidered gown and high Greek boots… Cleopatra’s children occupied four smaller thrones at the couple’s feet. In his husky voice Antony addressed the assembled multitude.

In an intentional provocation to Octavian, Antony distributed lands to his and Cleopatra’s children, making it abundantly clear that their family was the dynasty of the East.

For Octavian, this was a bridge too far. In 33 BC, the Triumvirate disbanded. The next year, Antony divorced Octavia. All pretenses of partnership and friendship between the two men were over. Shortly after the divorce, Octavian declared war on Antony’s true partner – Cleopatra.

Still, their power was no match for the Roman army

For all of Cleopatra’s riches, and the couple’s combined military prowess, they were no match for the Roman army. As Octavian and his forces closed in on Alexandria, the lovers continued their decadent parties, although they now called their drinking society “Companions to the Death.” Longtime advisors deserted, as did much of Antony’s army. While Antony was off battling Octavian’s forces, Cleopatra busied herself building a new “temple to Isis,” which she called her mausoleum. According to Schiff:

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Into the mausoleum she heaped gems, jewelry, works of art, coffers of gold, royal robes, stores of cinnamon and frankincense, necessities to her, luxuries to the rest of the world. With those riches went as well a vast quantity of kindling. Were she to disappear, the treasure of Egypt would disappear with her. The thought was a torture to Octavian.

Cleopatra staged a fake suicide, resulting in Antony’s own death…and Cleopatra ingesting poison

It also appears that Cleopatra was secretly negotiating with Octavian, unbeknownst to Antony. Always the more level-headed and strategic of the two, Cleopatra no doubt saw that Antony was doomed – but their children might not be. She had word sent to Antony that she had killed herself, knowing that he would soon follow. She was right. According to Plutarch, when Antony was told of his partner’s death, he uttered the immortal words:

O Cleopatra, I am not distressed to have lost you, for I shall straightaway join you; but I am grieved that a commander as great as I should be found to be inferior to a woman in courage.

After his attempted suicide, a distraught Cleopatra had Antony brought to her. Seeing what she had done, she was heartbroken but resolute. After Antony breathed his last, Cleopatra fought on, attempting to negotiate with Octavian. But all hope was lost, and Cleopatra snuck poison (or in some versions an asp) past Octavian’s guards. When Octavian realized what had happened, he sent soldiers to bust into the temple. There they found Cleopatra dead, her two attendants, Charmion and Iras, near death. According to Schiff:

Charmion was clumsily attempting to right the diadem around Cleopatra’s forehead. Angrily one of Octavian’s men exploded: “A fine deed this, Charmion!” She had just the energy to offer a parting shot. With a tartness that would have made her mistress proud, she managed, “It is indeed most fine, and befitting the descendant of so many kings,” before collapsing in a heap, at her queen’s side.

With Cleopatra’s death, Egypt became part of the Roman Empire. Caesarion was murdered, while Alexander Helios, Cleopatra Selene and Ptolemy Philadelphus were brought to Rome to be raised by Octavia. Her victorious brother erased all traces of the once glorious couple, but he did make one concession. Honoring her last request, he had Cleopatra and Antony buried side by side.