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"This is a great glimpse into the lives of celebrities before the world got to know them," said Auction Director Dan Imler.
The collection features President Woodrow Wilson's 1892 college yearbook, when he was a professor at Princeton, and a signed copy of Richard Nixon's high school yearbook.
President Bill Clinton's junior high yearbook is no doubt more valuable because of the signed note he wrote to a classmate in the back.
"He's pictured about ten times throughout that yearbook, so there's indications he was well on his way to becoming an accomplished individual," Imler said.
The collection once belonged to a Florida man who spent the last 15 years bidding on the books, and building a network of dealers.
The collection also includes hockey great Wayne Gretzky's high school yearbook and Jackie Robinson's 1938 Pasadena Jr. College yearbook, where he played baseball, basketball, football, and track and field.
Speaking of football, the yearbook of Peyton Manning is from when he was just a small boy.
"We actually have a yearbook from Peyton Manning from first grade. That's the earliest representation we have in the collection," said Imler.
Norma Baker's 1942 West Hollywood High School yearbook is probably the most coveted. It's the only one the future Marilyn Monroe is pictured in, because she dropped out in the 10th grade.
However, there are plenty of pictures of David Letterman, and Brad Pitt is seen with his frat brothers at the University of Missouri in 1986.
And who knew that Angelina Jolie, then Angelina Voight, went to the same Beverly Hills high school as Monica Lewinsky? Angelina was a Freshman when Monica was a Junior.
This auction runs until August 12th.
