Odd Company Through the Ages

Sometimes, the most fascinating parts of history are those that don't fit patterns. For example, think of two names you'd never expect in the same room—only to find out they shared meals or helped change each other's paths. These 20 pairings reveal how friendship often ignores norms. 

Ed Ford, World Telegram staff photographer on Wikimedia

1. Frank Sinatra and John F. Kennedy

When JFK was running for president in the 1960s, Frank Sinatra brought star power to his campaign. Though they vacationed together and drew crowds, Sinatra's mob ties became a liability, and in 1962, JFK ditched him.

Capitol Records on Wikimedia

2. Arthur Conan Doyle and Harry Houdini

They bonded over curiosity—Doyle's passion for spiritualism met Houdini's skepticism. At first, they admired each other's showmanship, but Doyle insisted Houdini had supernatural powers, even after repeated denials. This friendship collapsed by 1924, with public arguments filling newspapers.

Bain News Service, publisher on Wikimedia

3. Voltaire and Frederick the Great

This philosopher and king exchanged letters for decades. Voltaire moved to Frederick's court in 1750, enjoying music and political theory until quarrels drove them apart. Their final break came in 1753 after a pamphlet scandal, after whicih Voltaire fled Prussia, and Frederick confiscated his books and papers.

Arnaud 25 on Wikimedia

4. Alexander Graham Bell and Helen Keller

Bell met Keller in 1886 and helped arrange her education by connecting her with Anne Sullivan. She also stayed close, mentoring her and advocating for the deaf community. Keller later credited Bell for being the door that opened her world.

Harris & Ewing, photographer on Wikimedia

5. Mark Twain and Nikola Tesla

Twain loved Tesla's inventions so much that he often visited his lab in New York. One day in 1894, Tesla invited Twain to try his vibrating platform, and it reportedly relieved Twain's constipation instantly. Their friendship perfectly fit both their eccentric public images.

Ernest Herbert Mills on Wikimedia

6. Hunter S. Thompson and Pat Buchanan

It started with an interview, but Thompson kept returning to conservative Buchanan. Despite their clashing ideologies, Thompson admired Buchanan's blunt honesty. They argued and drank together through the '70s. Thompson once said Buchanan was "the sharpest mind on the right."

Photograph credited to "Cashman Photo Enterprises, Inc." Published by Random House. on Wikimedia

7. Mary Todd Lincoln and Elizabeth Keckley

Keckley, a former enslaved woman, began as Mary Todd Lincoln's dressmaker but soon became her confidante. She offered counsel during Lincoln's presidency and after his assassination. In 1868, Keckley's memoir revealed their closeness, sparking outrage and costing her elite status in Washington.

Mathew Benjamin Brady on Wikimedia

8. Groucho Marx and T.S. Eliot

Their correspondence began with Groucho joking about cigars and Eliot praising wordplay. It took years to arrange a meeting, but wen they finally met in 1964, Groucho brought bawdy humor. Eliot later framed Groucho's photo and kept it near his portrait of Yeats.

Orange County Archives from Orange County, California, United States of America on Wikimedia

9. Max Gendelman and Karl Kirschner

Captured during WWII, American soldier Max Gendelman befriended his German guard, Karl Kirschner, over chess and conversation in a prison camp. After the war, they reunited and remained lifelong friends. Gendelman later recounted their story in a memoir. 

Nach einem Gemälde in Schulpforta zunächst fotografiert, dann von Siegfried Brüggemann in Stralsund auf Stein gezeichnet und von Röpke gedruckt on Wikimedia

10. Ella Fitzgerald and Marilyn Monroe

In the 1950s, Ella Fitzgerald couldn't book top clubs due to segregation and perceptions of her performance style. Marilyn Monroe intervened, promising to sit front-row nightly if they booked Ella. The Mocambo said yes. Fitzgerald later said Marilyn "changed my career path permanently" with that gesture.

IISG on Wikimedia

11. George Washington and Elizabeth Willing Powel

Philadelphia socialite Elizabeth Powel wasn't just a hostess—she advised presidents. In 1792, she persuaded Washington not to resign after his first term. Their letters reveal her political insight and influence. Washington trusted her judgment, once calling her “the friend of many wise counsels."

Francis Alexander on Wikimedia

12. Duke Of Wellington and Harriet Arbuthnot

Harriet Arbuthnot, a diarist and political hostess, became the Duke of Wellington's closest female confidante during the 1820s. Her journals detail his daily life and private views. Despite Victorian norms, their friendship was accepted, and historians now rely on her diaries for insight.

John Hoppner on Wikimedia

13. Muhammad Ali and Malcolm X

They met in 1962 when Cassius Clay joined the Nation of Islam. Malcolm X became his spiritual mentor and shaped the boxer's transformation into Muhammad Ali, but political rifts split them by 1964. Ali later regretted abandoning him.

Knowle West Media Centre on Wikimedia

14. Andy Warhol and Jean-Michel Basquiat

What began as a mentor-protégé dynamic in 1983 evolved into one of art's boldest collaborations. Warhol, already a legend, embraced Basquiat's graffiti-inspired style. They painted together and challenged critics. Their 1985 show flopped—now, their work sells for millions worldwide.

Bernard Gotfryd on Wikimedia

15. Queen Victoria and Abdul Karim

In 1887, Queen Victoria appointed Abdul Karim as her servant. He became her teacher of Urdu, close advisor, and friend, sparking fury in royal circles. She defied protocol and called him “the Munshi.” After her death, the royal family erased his presence.

Rudolf Swoboda on Wikimedia

16. Albert Einstein and The Marangoni Family

In the 1890s, young Einstein vacationed in Italy and befriended the Marangoni family. Their uncle Carlo was a physicist who'd studied capillarity, and years later, Einstein's first paper explored the same topic. These early conversations helped direct his first published research in 1901.

Ferdinand Schmutzer on Wikimedia

17. Nelson Mandela and Fidel Castro

Mandela and Castro bonded over anti-imperialist ideology. Though controversial, their friendship was sincere, and in 1991, Mandela visited Havana, calling Castro “a source of inspiration.” Castro had supported ANC guerrilla fighters for decades. U.S. officials strongly objected, but Mandela never apologized for the alliance.

Bernard Gotfryd on Wikimedia

18. Eleanor Roosevelt and Amelia Earhart

Both pioneers in their fields, Roosevelt and Earhart formed a friendship grounded in courage and advocacy. For starters, they once ditched a formal dinner for a spontaneous night flight. Not only that, but Roosevelt later framed the license application Earhart gave her as a keepsake.

Harris & Ewing on Wikimedia

19. Wolfgang Pauli and Charlotte Houtermans

While escaping fascism in the 1930s, physicist Charlotte Houtermans found refuge with Wolfgang Pauli. More than a peer, he became her supporter in both science and exile. Their letters, preserved in archives, reveal how solidarity among scientists shaped resistance during Europe's darkest years.

Unknown authorUnknown author on Wikimedia

20. Nikola Tesla and Swami Vivekananda

Vivekananda and Tesla met in New York in 1896. Tesla, intrigued by Eastern philosophy, discussed energy and the Sanskrit term "prana." Vivekananda hoped Tesla would scientifically prove Vedic ideas, and although Tesla never formally pursued it, their exchanges are cited in comparative philosophy today.

Thomas Harrison on Wikimedia