JFK'S 'LAST' AUTOGRAPH
On Nov. 22, 1963, hours before he was killed in his motorcade, President John F. Kennedy signed a copy of the Dallas Morning News previewing his and the first lady's arrival in the city. Potentially Kennedy's last autograph, it was sold by the newspaper in 2009 for $39,000. At the same auction, a fedora worn by Dallas nightclub owner Jack Ruby when he fatally shot Kennedy's assassin, Lee Harvey Oswald, went for $53,775.
JESSE JAMES PHOTO
From 1866 to 1876, train robber Jesse James gained fame as a Robin Hood-style outlaw but rarely signed autographs due to the price on his head. One of those that survived was a famous portrait believed to be the only photo of James he personally signed, which sold in 2011 for more than $50,000.
ALBERT EINSTEIN LETTER
In December 1925, physicist Albert Einstein wrote a letter to engineer Giovanni Giorgi. In 2015, it was auctioned for $75,000. In the letter, Einstein wrote hypothetically about God's creation and referenced his most famous scientific contribution, saying, in part, "God created the world with more intelligence and elegance. ... I do not doubt the validity of the theory of relativity."
ALBERT EINSTEIN TONGUE PHOTO
In some corners of the web, it sometimes seems as though Einstein is as famous for sticking out his tongue as he is for his theory of relativity. No wonder an autographed copy of the heavily memed photo sold for nearly $75,000 at a 2009 auction. More recently, another auction-goer paid $125,000 for a matte-finish print of the same photo, autographed by Einstein in German. The message translates to: "This gesture you will like because it is aimed at all of humanity. A civilian can afford to do what no diplomat would dare."
JIMI HENDRIX'S FIRST CONTRACT
Guitar icon Jimi Hendrix was one of many 1960s musicians duped into signing contracts virtually robbing them of revenues and future royalties for their songs. In Hendrix's case, he signed an agreement with PPX Enterprises in 1965 in exchange for just $1 and 1 percent of the profits from his music sales. The contract, which sparked a legal battle following Hendrix's success, sold for $191,000 at auction.
F. SCOTT FITZGERALD BOOK
Autographs by Lost Generation literary icon F. Scott Fitzgerald are fairly uncommon in general, but the signature that earned $191,000 at auction in 2015 had pedigree beyond its rarity. It was in a first edition of Fitzgerald's famous novel "The Great Gatsby" made out to screenwriter Harold Goldman, whom Fitzgerald dubbed "the original 'Gatsby.'"
JOE DIMAGGIO & MARILYN MONROE BASEBALL
New York Yankee Joe DiMaggio and actress Marilyn Monroe were one of the 20th century's most talked-about celebrity couples. A baseball autographed by both sold for $191,200 at a 2006 auction. Oddly enough, another ball signed by Monroe using her given name, Norma Jean, sold for only $50,000.
BABE RUTH BASEBALL
Even DiMaggio and Monroe's combined fame can't compare to the Great Bambino's. One baseball signed by legendary Yankee pitcher and slugger Babe Ruth sold for $388,375 — up from $86,000 several years prior — at a 2012 auction, which also saw Ruth's 1927 game bat go for exactly the same price.
BANNED FIRST EDITION OF 'ULYSSES'
Irish author James Joyce's seminal work "Ulysses" was banned in both the U.S. and U.K. upon release in 1922 for sexually explicit content, making early copies hard to come by and correspondingly pricey. In 2009, a signed copy from the novel's original run of 100 sold at a London auction for 275,000 pounds, the highest recorded price for any 20th-century first edition. The book was in mint condition and unread but for the racy passages.
HALL OF FAME BASEBALL
As expensive as Babe Ruth's autograph alone was, the price skyrocketed when accompanied by the signatures of 10 other original baseball Hall of Famers. Auctioned for $632,369 in 2018, the most expensive autographed baseball ever bears the signatures of 11 early baseball greats including Ruth, Ty Cobb, Connie Mack, and Honus Wagner — the only surviving members of the Hall of Fame's original 25 inductees when it opened in 1939.
OBSCURE FOUNDING FATHER'S SIGNATURE
You don't really hear about Button Gwinnett, but he's one of America's founding fathers. He wasn't that well-known before the Continental Congress and died in a duel 10 months after signing the Declaration of Independence. Since only 51 of Gwinnett's signatures are known to exist, one such example on a business document from 1773 sold at auction in New York for more than $722,500.
JOHN LENNON ALBUM OWNED BY HIS KILLER
On Dec. 8, 1980, John Lennon signed a copy of his latest album, Double Fantasy, for Mark David Chapman, a mentally troubled fan who would assassinate the rock musician and former Beatle that night. Later discovered in a planter outside Lennon's New York home, the autographed album has changed hands twice for steep prices: first for $150,000 in 1999 and then for $850,000 in 2010. In 2017, it was listed again for a whopping $1.5 million.
BABE RUTH'S YANKEES CONTRACT
Price: $2.3 million
Babe Ruth left the Boston Red Sox to join the New York Yankees in 1919 and began breaking baseball records in his first of 15 seasons for the team. Almost a century later, the contract Ruth signed with the Yankees, making league history, sold at a 2017 auction for $2.3 million — the highest amount for any sports document. (Also sold at the same auction was Ruth's 1927 World Series ring. Both had been owned by actor Charlie Sheen.)
ROCK STAR GUITAR
Price: $2.7 million
The world record holder for most expensive guitar ever sold at auction is a Fender Stratocaster signed by a collection of U.K. rock icons including Paul McCartney, Keith Richards, Mick Jagger, Eric Clapton, Jimmy Page, and Brian May. It didn't hurt that payment for the musical totem was going to charity, as well. The guitar was bought for $2.7 million at a Qatar auction, with proceeds going to the Reach Out to Asia program, which works to ensure young people access to education.
ANOTHER ALBERT EINSTEIN LETTER
Price: $2.9 million
Not to be outdone by Babe Ruth, Albert Einstein makes his third appearance on this list, with another handwritten letter about God. In this famous correspondence from 1954, recently auctioned for nearly $3 million, Einstein lays out his religious beliefs (or lack thereof) candidly and in depth, writing, "The word God is for me nothing but the expression and product of human weaknesses, the Bible a collection of venerable but still rather primitive legends."
ABRAHAM LINCOLN LETTER
Price: $3.4 million
The authentic writings Abraham Lincoln have often fetched high prices, but the record was set in 2008 when a letter sold for a staggering $3.4 million at a Sotheby's auction. The letter is a response to a petition signed by 195 children requesting that Lincoln "free all the little slave children in this country." In it, the 16th president says, in part, "While I have not that power to grant all they ask, I trust they will remember that God has, and that, as it seems, He wills to do it."
RFK'S COPY OF THE EMANCIPATION PROCLAMATION
Price: $3.7 million
Signed by President Abraham Lincoln and owned by one-time presidential candidate Robert F. Kennedy, a printed copy of the 1863 Emancipation Proclamation was auctioned off by Kennedy's estate in 2010 for more than $3.7 million. This particular copy of the historic act was one of 48 originally signed by Lincoln, of which only half are known to survive, with only eight to 10 in private hands.
GEORGE WASHINGTON'S ANNOTATED CONSTITUTION
Price: $9.8 million
In his lifetime, the first U.S. president kept a bound volume of the Acts of Congress, including the Constitution and Bill of Rights, with his signature of ownership and handwritten annotations in the margins. Dating back to 1789, the historic document set auction records in 2012, when it sold for the exorbitant price of $9.8 million.