"Summertime" (Miles Davis)

I took voice lessons for a hot second back in high school.  My voice teacher (and I use the term "teacher" loosely) was a music professor at the small liberal arts college in my hometown.  He was consistently late to our appointments and was always distracted.  That is, when he bothered to show up at all.  Which really sucked, because I had to pay the guy for a month of lessons in advance, and the money was coming out of my own measly checking account.
One afternoon, we're plodding through Giordani's aria "Caro Mio Ben."  He's bored and distracted, which is making me bored and distracted.  So I start scanning his bookshelf (while I'm still belting out the song in Italian), and I see a copy of the Miles Davis-Gil Evans 1958 reimagining of George Gershwin's Porgy & Bess on the shelf.  So during a short water break, I ask him about it.
"I have a Miles Davis compilation album of his early Blue Note recordings.  Is this one good, too?"
He looked at me like I'd ripped one.  "Is it good?"
As I stumbled and stammered, trying to explain that I was just getting into jazz, and that I'd heard a mid-60s album Davis had recorded and didn't care for it, he stopped me.
"Yeah.  It's good."
He cut the lesson short by 15 minutes that afternoon, in an obvious rush to be somewhere else.  Incidentally, there was no next lesson.  Not because I pulled the plug.  (I should have, though.)  He just never showed up again.
About a month later, I ran into a girl I knew who'd also been taking lessons from him.  She filled me in that he'd been having an affair with the Dean of Students.  Apparently, they had both packed up and left town together right after my final lesson without giving anyone, including the college, any notice.
Anyway, when he cut my last lesson short, I walked across the street to our town's lone record store, where I asked the owner about Davis's Porgy & Bess.  There was no eye-rolling or irritated looks.  He just popped in the CD, and we listened to it over the PA system and talked music for about an hour.  I ended up spending the money set aside for the next month's voice lessons on Davis's Porgy & Bess and Kind of Blue.  Good investments, I'd say.
Regarding "Summertime" specifically, it's one of my favorite pieces of instrumental jazz.  Evans's arrangement strips Gershwin's aria down to its skeleton, turning it into a modal piece built upon lush, sultry chords, thereby giving Davis the freedom to stick to or stray from the melody as he pleases.  In three sophisticated minutes, it captures the swelter of a South Carolina Lowcountry summer night and also pays homage to Gershwin without being a carbon copy of the original.

"All Blues" (Miles Davis)

Along with the iconic “So What,” the track “All Blues” also is a cornerstone of the jazz classic, Kind of Blue (1959).  Much like “So What,” there was little or no practice before the musicians recorded "All Blues."  Miles Davis told them the basic structure and the chord changes he had in mind, and away they went.  
It’s Take #2 that you hear on the album.
The song gets its name from its core musical structure: the 12-bar blues.  That said, Davis doesn’t exactly have his musicians play the game straight.  Instead of sticking to a traditional I chord/IV chord/V chord blues progression, they move around the scale a bit, dipping to minor chords and chromatic chords outside the scale along the way, creating alternating waves of electrifying dissonance and mellow resolve every few measures.
Also, Davis utilizes waltz-like 6/4 time instead of common 4/4 time, giving the song a special, lilting swing that the musicians ride for well over 11 minutes.  
Although, it doesn’t feel like 11 minutes.
In fact, it’s not uncommon for me to hit “repeat” three or four times on this track.

"So What" (Miles Davis)

So Miles Davis books time at Columbia's 30th Street Studios for March 2, 1959.  He has a basic idea of what he's looking to record: songs built around basic chords and scales--modes, if you will.  He has a few melody lines sketched out in his head.  But as far as actual "compositions," nothing is written down or meticulously arranged--a direct contrast to his most recent work with arranger Gil Evans.
The musicians (consisting of Bill Evans on piano, Julian "Cannonball" Adderley on alto sax, John Coltrane on tenor sax, Paul Chambers on bass, and Jimmy Cobb on drums) come in for the recording date.  There's little or no rehearsal.  Davis in his badass growl gives them a basic idea of the scales and the changes, and the tape starts rolling.
Evans and Chambers set the tone by playing some scales before Chambers suddenly plays this riff that becomes the foundation of the hook.  Then, Evans follows by playing these accentuating block chords.  After a couple of bars, Davis, Adderley, and Coltrane fall in, playing the two-note pattern: bahhh...baaap...bahhh...baaap...soooo...what
And the rest is serendipity, sheer talent, and a little ESP.

"In a Silent Way" (Miles Davis)

For as wild and funky as Miles Davis and his collaborators got on 1970's Bitches Brew, I prefer In A Silent Way (1969) and its smooth yet thrilling title track.  
Davis had flirted with mixing electric instruments and rock textures into jazz starting with the album Miles in the Sky (1968).  But this was the first time he went full-on switched-on--with stunning results.
The song "In A Silent Way" is really a three-part medley of two pieces: the majestic, ethereal "In A Silent Way," which bookends the undulating "It's About That Time."  
There's very little in the way of typical jazz soloing on the track; no one steps into the spotlight for his 12 bars and then lets the guy next to him blow for his 12 bars, in other words.  It's more about everyone contributing to the texture of the music and keeping the groove tight, with Wayne Shorter contributing a short but expressive passage on soprano sax followed by Davis doing the same on horn.
The title aptly describes the feeling of the song.  I always envision snow falling in the midst of an urban landscape--Mother Nature blanketing the city with a delicate, frozen calm and a pin-drop silence that envelopes the world before the snow plows have a chance to disrupt it all.  (Or at least that's how it sounded during yesterday's blizzard here in New York.)

"Autumn Leaves" (Cannonball Adderley)

Originally a French song ("Les feuilles mortes," or "The Dead Leaves") written in 1945, American lyricist Johnny Mercer gave the song English lyrics and its new title ("Autumn Leaves") in 1950.  Since that time, everyone and his brother, from Louis Armstrong to Eric Clapton, has covered it.  Sometimes ten times over.  (The site Current Research in Jazz says that it has been recorded more than 1400 times, making it the 8th most-recorded jazz standard of all time.)
This particular rendition by alto sax player Julian "Cannonball" Adderley was recorded in 1958 for Blue Note Records.  In actuality, the session was supposed to have been credited to superstar trumpeter Miles Davis.  But for contractual reasons (Davis was signed to Columbia in the late 50s), the resulting album, Somethin' Else, was credited to Adderley.  
(A year later, Adderley also would take part in the sessions that would produce Davis's modal jazz masterpiece, Kind of Blue.)
Regardless of who got top billing, Somethin' Else (and, specifically, "Autumn Leaves") represents five seasoned jazzmen playing and improvising at their collective best.
Davis, who runs the proverbial show, plays his trumpet with a Harmon mute throughout, creating this sensuous sound that is both sexy and moody, even a little sad.  It somehow feels very French, and it perfectly evokes the exact sense of longing in Mercer's lyrics, which recount memories of lost love, without ever uttering a word.  
From a technical standpoint, his soloing on this track may be some of his "cleanest" and most confident on record.  By that, I mean he had the tendency to flub notes and overreach his entire career.  
There, I've said it.  
I love Miles and his creativity, but he was not the most technically proficient trumpeter out there.  (For instance, check out his and Gil Evans's take on Gershwin's Porgy & Bess sometime.  It's ambitious and genius.  But Miles flubs notes and goes flat all over that record.)  Dizzy Gillespie, Art Farmer, Donald Byrd, Wynton Marsalis, and tons of other guys are/were a hell of a lot better at breath control and doing it fluid.  
Anyway, I'll get off my soapbox now.
For the most part, Davis sticks pretty closely to the melody on his solos (his second and final solos are slight exceptions), adding a few runs here and there. However, Adderley carves out his own path entirely, playing these haunting runs and sneaking in tasty blue notes.  It's a controlled performance but it has this lilting swing, kindling mental pictures of red and orange leaves catching the chilly Fall breeze and swirling in the air before they come in for a landing.
Hank Jones solos after Davis's second solo.  His patterns on piano actually kind of mirror the feel of Adderley's solo: controlled yet creative and swinging, too.
Art Blakey (drums) and Sam Jones (upright bass) never actually solo on this track.  However, they do provide one hell of an anchor.  Blakey (who could rip up a drum solo like no one's business) simply sticks to brushes, providing this swinging shuffle that perfectly captures the crunch of fallen leaves under one's feet.  Jones mostly provides a walking bassline throughout that is subtle and tasteful.  The two places that Jones varies from this are in the intro and the coda--the latter being my absolute favorite part of the song.  
In the coda, Sam Jones's bluesy riff and Blakey's brushes beneath Hank Jones's delicate piano are as smooth and velvety as aged Scotch.  Then Davis's horn comes in for one final appearance, and it's bathed in sultry reverb and pure blues.  (It's almost worth skipping ahead to about the 9:00 mark and just letting that part soak into your brain.)  It's 2 minutes of everything that I love about Cool Jazz: sophisticated, oblique, soulful, and hypnotic.
It's just a great rendition of a classic tune.