Year: 1959
Record label: Columbia
Worth Today: $1,000*

They just don’t make ‘em like Miles Davis anymore. The jazz genius paved the way for others like him, but can never be imitated. Davis released Kind of Blue in 1959 on Columbia Records, cementing his status as the King of Cool. 

Not only is Kind of Blue one of the greatest jazz records of all time, critics have long regarded it as Miles Davis’ masterpiece. Kind of Blue would go on to deeply influence many different genres, including classical, rock, and jazz, and the Library of Congress archived it in 2002.

Over the course of his career Miles had the pleasure of working with a variety of other skilled instrumentalists, from John Coltrane to Bill Evans. An original pressing of the 60-year-old record can fetch around $1,000. It may not be the most expensive record in history, but it’s worth a darn sight more than your average slice of acetate.