Jazz at Massey Hall - Charlie Parker, Dizzy Gillespie, Charles Mingus, et al. (released in 1953)
The greatest live album I've had the pleasure to hear.
Birth of the Cool - Miles Davis (released in 1957)
Miles Davis at his best. Based on the first track alone, "Move", this is a must buy.
Giant Steps - John Coltrane (released 1960)
The track for which this album is named from is one of the top 10 greatest jazz pieces of all time. Needless to say, this album should be on every jazz collector's shelf.
Time Out - Dave Brubeck Quartet (released in 1959)
Includes the legendary "Take Five", which includes a solo by one of the great drummers of jazz, Joe Morello.
Bitches Brew - Miles Davis (released in 1970)
My favorite Avante-Garde jazz album of all time,