Obviously, this type of posts opens more doors than it closes.
Have I seen Ken Burns’ Jazz? Nope, but I hear it provides a good overview (but since jazz lovers, by definition, are a peculiar lot who don’t follow anyone’s lead, have many, many problems with who Burns mentioned, lavished attention on, or left off) - so maybe you could get his series and take it from there.
Early Jazz - Louis Armstrong’s Hot Fives and Hot Sevens recordings, Jelly Roll Morton
Swing Jazz - Benny Goodman (esp. featuring Charlie Christian), Duke Ellington, Gerschwin. Buy Ben Webster - King of the Tenors for mellow, combo-style of this stuff. He was Duke’s tenor sax.
Be-Bop - Charlie Parker - Yardbird Suite rocks, Gillespie - anything with Salt Peanuts, Oleo, etc…, Bud Powell (piano - wow) - best of, Thelonius Monk - Straight, No Chaser, Underground, Composer, Brilliant Corners, plenty of others,
Hard Bop - Coltrane - A Love Supreme, Blue Trane, Coltrane Plays the Blues, Giant Steps (getting a little out there). Art Tatum - 20th century piano genius is amazing stuff…
Cool Jazz - Miles (Kind of Blue, Steamin’, Relaxin’, Cookin’, Walkin’ - many, many more), Brubeck - Time Out, Teddy Edwards - Sunset Eyes, Sonny Rollins - Saxophone Colossus, Art Pepper - Meets the Rhythm Section. Plenty of other West Coast stuff, like Gerry Mulligan, or Paul Desmond, but this is a start.
There are about 20 plus CD’s all of which are 5-star classics. Hope that helps.