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When imagining the lives of historical figures, we often picture them as people who were extremely focused on their achievements. It’s easy to think of them as not having the time to socialize, let alone make friends. However, many prominent historical figures formed strong connections with other big names of their time. Some of the connections gradually faded, while others stood the test of time and distance. These unlikely friendships often challenged each figure to consider a different perspective and find common ground. From an author befriending a scientist to a wrestler building a bond with a playwright, we’ve gathered 21 pairs of historical figures you wouldn’t have thought were friends.

#1

Ella Fitzgerald And Marilyn Monroe

Portraits of two iconic historical figures, symbolizing unexpected friendships between historical figures from different backgrounds.

Both Ella Fitzgerald and Marilyn Monroe rose to fame in the 50’s. They became close friends because of the many things they had in common, such as their traumatic upbringings. Marilyn helped take Ella’s career to the next level by getting her gigs in fancy clubs she wouldn’t have managed to get into because of racial prejudices at the time. Their friendship lasted till Monroe’s passing in 1962.

Sara Kettler , Carl Van Vechten , Bert Parry Report

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    #2

    Hunter S. Thompson And Pat Buchanan

    Black and white photo collage showing two historical figures engaged in conversation illustrating unexpected friendships between historical figures

    Hunter S. Thompson, a counterculture journalist, and Pat Buchanan, a conservative politician turned political commentator, met during Nixon’s 1972 campaign. Though they had different ideologies, they appreciated each other’s honesty and found it enjoyable to talk to one another. The pair managed to build a very close friendship by putting their political views aside and often spoke highly of each other.

    Ann S. Epstein , Annie Leibovitz , U.S. National Archives and Records Administration Report

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    #3

    Arthur Conan Doyle And Harry Houdini

    Portraits of two historical figures highlighting unexpected friendships between notable individuals from history.

    Arthur Conan Doyle, the creator of Sherlock Holmes, and Harry Houdini, a famous illusionist, had an interesting friendship. They found common ground in spiritualism, but eventually cut ties with each other because of it. Doyle’s wife, a self-proclaimed medium, performed a seance to contact Houdini’s deceased mother. Houdini's mother made contact through 15 pages of writing. But knowing his mother wasn’t good at writing in English, Houdini denounced the authenticity of the writing. This sparked the eventual breakdown of their friendship.

    Lyn Gardner , Walter Benington , Wikimedia Commons Report

    Fat Harry (Oi / You)
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Houdini was a famous skeptic and would debunk spiritualist nonsense. Conan-Doyle was a firm believer.

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    #4

    Helen Keller And Mark Twain

    Black and white portraits of two historical figures symbolizing unexpected friendships between historical figures in different eras.

    Helen Keller, a deaf and blind writer, and Mark Twain, an author, met at a party in New York City in 1895. Keller was just 14 years old when they met, while Twain was in his 50s. Despite their age gap, the two developed a close friendship because of their shared love for humor and learning. Twain admired her so much, he even organized sponsors for her studies at Radcliffe College.

    Hadley Meares , Wikimedia Commons , A.F. Bradley Report

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    #5

    Mary Todd Lincoln And Elizabeth Keckley

    Black and white portraits of two women representing unexpected friendships between historical figures in the 19th century.

    Mary Todd Lincoln, former First Lady of the United States, was close friends with her dressmaker, Elizabeth Keckley, a former slave who bought her own freedom. The pair often confided in each other and worked together to raise money during the Civil War. Their friendship fell apart when Keckley published a memoir revealing details that violated Lincoln’s privacy.

    Wikipedia , Shepherd, Nicolas H. , collectionsconversations Report

    #6

    J. R. R. Tolkien And C. S. Lewis

    Two historical figures pictured in black and white, highlighting unexpected friendships between historical figures.

    J. R. R. Tolkien and C. S. Lewis were two authors who forged a close literary friendship in the 20th century. Despite their differences, they joined a writers' group called the Inklings at Oxford, where they would share ideas and discuss manuscripts. Both writers had a great influence on each other and often collaborated creatively. Tolkien even influenced Lewis to convert to Christianity from Atheism.

    Geneva Blog , epistleofdude , Levan Ramishvili Report

    Huddo's sister
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I've always thought of them as being similar so this never seemed an unlikely friendship. I must say the movie Tolkien was brilliant though.

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    #7

    John F. Kennedy And Frank Sinatra

    Portraits showing two historical figures, representing unexpected friendships between historical figures in different eras.

    John F. Kennedy and Frank Sinatra were two of the most distinguished figures in their time, one in politics and the other in the entertainment industry. Not only were they very good friends, but they also shared interests. Reportedly, Sinatra used his star power to garner support for Kennedy among other high-profile entertainers. He even recruited Sam Giancana, a Chicago mob boss, to sway the votes of union workers in Kennedy’s favor. Their friendship, unfortunately, crumbled after Kennedy took office.

    Tim Ott , Cecil Stoughton , The Hollywood Reporter Report

    Michael Largey
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Sinatra had invited Kennedy to stay at his house when Kennedy visited California. Kennedy initially accepted, and Sinatra had a helipad built on his property so the presidential helicoptor could land there. Kennedy was talked out of staying with Sinatra because of the latter's mob ties. Sinatra went into a rage and destroyed the the helipad himself with a sledgehammer. He turned Republican and expelled Kennedy brother-in-law Peter Lawford from the Rat Pack.

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    #8

    Nikola Tesla And Mark Twain

    Black and white portraits of historical figures highlighting unexpected friendships between notable historical figures.

    Nikola Tesla, a scientist, became friends with Mark Twain, a famous author, in the 1890s. They exchanged many letters throughout their friendship and came to admire and respect each other’s craft. Twain had an interest in technology and was fascinated by Tesla’s lab, while Tesla described Twain’s early works as instrumental in his recovery from a life-threatening illness.

    Paul Ratner , Napoleon Sarony , Abdullah frères Report

    Huddo's sister
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    I am amused by how many of these people are fictionalised in the tv series The Murdoch Mysteries. Wildly inaccurate though it is.

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    #9

    Samuel Beckett And André The Giant

    Side-by-side portraits of two historical figures illustrating unexpected friendships between historical figures.

    André the Giant, a French professional wrestler, found a good friend in the Irish playwright Samuel Beckett. They met in France in 1953 after Beckett befriended a local carpenter, Boris Rousimoff, who happened to be André’s father. Beckett would drive André to school every day because his truck was the only one big enough to fit him. The two became close friends through their conversations during the ride to school.

    Ann S. Epstein , Roger Pic , Wikipedia Commons Report

    #10

    Buster Keaton And Harry Houdini

    Black and white portraits of two historical figures highlighting unexpected friendships between historical figures.

    Silent film actor Joseph Frank Keaton got his stage name from Houdini, the illusionist. Houdini owned a traveling show with Keaton’s father, his business partner. Allegedly, while visiting Keaton’s family, Houdini saw little Joseph fall down some stairs at six months old and commented on how well he took a “buster”. From then on, Joseph was known as Buster Keaton.

    Ann S. Epstein , Bain News Service , The New York Times Report

    #11

    Joe Louis And Max Schmeling

    Two historical figures in black and white photos, illustrating unexpected friendships between historical figures.

    Joe Louis and Max Schmeling were rival boxers during the 1930s. Schmeling, from Germany, was the world heavyweight champion at the time, and Louis, a black American, was a rising boxing star in America. The matches between them were often viewed as fights between Americanism and Nazism by the public. But the two boxers actually disliked the fact that this symbolism was forced on them. Although separated during WWII, the two reunited after the war and stayed friends for the rest of their lives.

    Duo Dickinson , Marylandstater , German Federal Archives Report

    #12

    Ulysses S. Grant And James Longstreet

    Two historical figures in formal 19th-century attire, symbolizing unexpected friendships between historical figures.

    The friendship between Gen. James Longstreet and Gen. Ulysses S. Grant was a rare one in American Military history. They met when they were cadets at West Point and became close friends soon after. Both men fought on opposite sides during the Civil War — Longstreet for the Confederacy and Grant for the Union, but still managed to rekindle their friendship after the war.

    Grant Cottage , Brady-Handy Photograph Collection, Library of Congress , Gamaliel Bradford Report

    Michael Largey
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Longstreet was one of the Confederacy's two or three best generals. But unlike many other Southern generals, no statue of him has ever been put on display in the South. This may be due to the fact that after the war he worked to see that the former slaves had full rights as citizens.

    #13

    Prince And Muhammad Ali

    Split image showing a historic performance and a close-up portrait, symbolizing unexpected friendships between historical figures.

    Prince and Muhammad Ali formed a close friendship after meeting before one of Ali’s charity events. Prince enthusiastically agreed to meet Ali in Washington at short notice to support the boxer's World Healing Project. They immediately hit it off because of their shared admiration and respect for one another. The two remained close friends till Prince’s passing in April 2016. Shockingly, Ali passed away only two months after Prince.

    BBC , Warner Bros. , Bernard Gotfryd Report

    #14

    Emily Dickinson And Thomas Wentworth Higginson

    Portraits of two historical figures side by side, illustrating unexpected friendships between historical figures.

    Emily Dickinson, a poet, and Thomas Wentworth Higginson, an author at the time, only met in person twice, but had a long-lasting connection. Higginson became her mentor and supported her writing after she sent him a letter asking if he thought her poems were “alive.” From then on, they exchanged hundreds of letters and poems until Dickinson’s passing in 1886. Higginson kept her voice alive by helping publish her poems.

    Emily Dickinson Museum , Wikimedia Commons , Wikimedia Commons Report

    #15

    T. S. Eliot And Groucho Marx

    Black and white photos of two historical figures illustrating unexpected friendships between historical figures in formal attire.

    T.S. Eliot, a British poet, and Groucho Marx, a comedian, became friends in 1961 when Eliot wrote a fan letter to Marx. They exchanged autographed photos and wrote multiple letters to each other before their meeting in 1964. The two had a tense friendship, mostly because they represented two different social types. One instance of this tension was a heated exchange over whether Eliot kept his promise to hang Marx’s autographed photo alongside those of his other friends.

    Lee Siegel , Lady Ottoline Morrell , Los Angeles Daily News Report

    Michael Largey
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    "The Love Song of J. Alfred Hackenbush" would have been interesting to read.

    #16

    Martha Stewart And Snoop Dogg

    Musician and TV personality shown side by side, representing unexpected friendships between historical figures.

    Martha Stewart and Snoop Dogg may seem like quite an odd pairing, but they quickly became close friends when they met on her show in 2008. While they enjoyed baking together, it was their sense of humor that made them close. They have gone on to collaborate on new cooking shows, guest-star on other shows, and even release new products together.

    Elizabeth Logan , Bruce Baker , Gage Skidmore Report

    WindySwede
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    though historical, with both living?

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    #17

    Colonel Sanders And J. Edgar Hoover

    Two historical figures, one writing and one holding documents, highlighting unexpected friendships between historical figures.

    While the two had a pretty loose connection, Colonel Sanders, founder of KFC, often sent letters of admiration to J. Edgar Hoover, the director of the FBI, in hopes of starting a friendship. One of the letters was an invitation to his 80th birthday party. Reportedly, these letters were added to a 15-page FBI file with background information about the Colonel.

    Nick Desimone , Edgy01/Dan Lindsay , Marion S. Trikosko Report

    Dori
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    That sounds like something Hoover would do.

    #18

    Alexander Graham Bell And Helen Keller

    Black and white photos of two historical figures, showcasing unexpected friendships between historical figures.

    Alexander Graham Bell is not only known for inventing the telephone, but also for his extensive work in the deaf community. In 1886, Bell helped arrange for Anne Sullivan to become Helen’s home school teacher. He even started a trust fund for her to attend her dream college, Radcliffe. The two developed a father-daughter bond over time, with Helen appreciative of Bell for broadening her horizons, and Bell of Keller for bringing national attention to deaf education.

    David Blatty , Moffett Studio , Los Angeles Times Report

    Huddo's sister
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Weren't they both advocates for eugenics 'as was the fashion at the time'?

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    #19

    Lucille Ball And Carol Burnett

    Two historical figures shown in portraits, illustrating unexpected friendships between historical figures across time.

    Lucille Ball and Carol Burnett built a friendship around their love for comedy. The two comedians frequently appeared on each other’s shows, and Burnett leaned on Ball for guidance when it came to navigating the male-dominated entertainment industry. Burnett often admired Ball for her ability to voice her opinion like a man would. They remained close friends until Ball’s passing in 1989.

    Matt Mullen , CBS Television , CBS Television Report

    Rebecca Ferguson
    Community Member
    5 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Not too sure this could be classed as an unexpected friendship at all.

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    #20

    Bob Hope And Dwight D. Eisenhower

    Black and white photo of a man in formal wear next to a color portrait of a man in a gray suit representing historical figures friendship.

    Hitting it off in 1943 during the war, the pair became friends after Hope, a comedian, entertained Eisenhower and his troops in Algiers. Despite Eisenhower becoming President a decade later, they continued to spend time writing and playing golf with each other. Their wives also became quite close because of how much time they spent together.

    Ann S. Epstein , NBC Television , White House Report

    #21

    Larry Flynt And Jerry Falwell

    Portraits of two men in suits representing unexpected friendships between historical figures in formal settings.

    Larry Flynt, an adult content publisher, and Jerry Falwell, a conservative preacher, somehow found common ground and kept in contact with each other for many years. They initially met when Falwell sued Flynt over a parody interview that made disturbing claims about intimate relations between Falwell and his own mother. After the trial ended, the two reunited on the Larry King Show to promote their own projects, resulting in them collaborating on a series of debates at colleges across the country.

    Nicholas Goldberg , Toglenn , Liberty University Report