"Do It Again" (Steely Dan)

It's still amazing to me that Steely Dan pulled off the feat of having a hit album its first time out of the gate with Can't Buy a Thrill (1972).  And had an instant #6 hit song with "Do It Again."  Not that the album or the single aren't great; they are.  It's just that, for a band named after a sex toy in the William S. Burroughs novel Naked Lunch and a quirky debut single that tells an odd tale of some junkie gambler who shoots a guy and then ends up on a debauched spree in Vegas, I'm surprised it fared as well as it did in the bubblegum musical landscape of 1972.  After all, we're talking a period of time when a pubescent Donny Osmond was ruling the charts.
Anyway, "Do It Again" is a surprisingly strong single for a band that essentially was just getting started.  Its undulating Latin funk makes it easy to mistake for a Santana song; even Denny Dias's fluid, surprisingly effective solo momentarily makes one wonder if Carlos Santana decided to pick up an electric sitar for s's and g's.  But it's Donald Fagen's distinctive jazz-tinged vocals that really let you know it's Steely Dan and no one else.  (Funny to think that Fagen initially was reluctant to be the band's lead singer.  I can't picture what albums like Countdown to Ecstasy or Aja would have sounded like without his "yeah, I'm from South Jersey; what of it?" vocals.)

"Song for My Father" (Horace Silver)

I really got into jazz as a teenager.  It stemmed from listening to groups like A Tribe Called Quest and De La Soul and then scanning the song credits to figure out where they were getting those sick jazz breaks and beats.  Pretty frequently, I was seeing the phrase "sample courtesy of Blue Note Records."  So I went hunting for stuff on the Blue Note label at the record store.
I didn't realize it at the time, but Blue Note had been defunct for quite a few years, the result of acquisitions and mergers and all of the stuff that has nothing (and everything) to do with how one consumes music.  So finding reissues of the back catalog wasn't easy at first.  Although, my guess is there were enough people like me, hearing these jazz breaks on hip-hop records and then specifically asking for this music, that the people holding the purse strings realized the Blue Note brand still had cache and there was money to be made reissuing the old albums.
Anyway, the first jazz album I ever bought was a compilation of hard-bop jazz, The Best of Blue Note (1991), and one of my favorite tracks on that compilation was pianist Horace Silver's "Song for My Father," a bossa nova groover with a memorable hook and funky/churchy soloing by Silver and tenor saxophonist Joe Henderson.
Story goes, Silver was inspired to record the tune and ultimately the Song for My Father album (1964) after a trip to Brazil.  The excursion allowed Silver to reconnect with his roots—his father having hailed from the Cape Verdean island of Maio, a former Portuguese possession off the western coast of Africa.  Thinking about those influences, it's only natural the track "Song for My Father" would blend Brazilian bossa nova with a touch of African/island folk.
As a keyboardist myself, what appealed to me about the track is that it's very piano driven; Silver solos for more than half the song.  It also has this interesting mix of funky block chords and bluesy runs.  It's a great piece to warm up and/or practice with because it has that kind of variety.  Its cyclical structure and repeating bassline also sort of give you the freedom to noodle around and invent new riffs, runs, etc.
I even played it a few times for audiences, who immediately assumed that I was about to deliver an acoustic rendition of "Rikki Don't Lose That Number."  (Steely Dan borrowed the opening notes of "Song for My Father" for its 1974 hit.)

"Peg" (Steely Dan)

By the time Steely Dan recorded its 1977 album Aja, the "band" consisted only of guitarist/bassist Walter Becker, vocalist/keyboardist Donald Fagen, and a revolving array of session players who were picked for what they could bring to an individual song.  Not a bad approach, actually.  If one player has blues chops, you plug him into a song that needs a bluesier feel.  Or if something calls for a jazzier approach, you use the guy who's a Wes Montgomery disciple for the guitar solo instead of the guy who was reared on Chuck Berry.  It was a smart way for Becker and Fagen to broaden Steely Dan's sonic palette and create music the way they heard it in their heads.
Anyway, the track "Peg" from Aja is what you get when Becker and Fagen create a "pop" song.  Its augmented blues structure makes it instantly accessible and familiar.  But then they throw in some quirky melodic twists (like the jazz-steeped chord changes on the chorus) and arranging innovations (like having Michael McDonald's backing vocal doubled by reed player Tom Scott on his Lyricon—an electronic sax-like instrument—to make the word "Peg!" sound strangely electronic and robotic) that catch you off guard and make you want to listen to it again, just so you can figure out what the hell is going on.
And then there's the lyrics.  In true Steely Dan fashion, they're smart but vague in their thrift.  The song is ostensibly about a young starlet who's about to get her big break in the movies.  However, Fagen drops subtle clues as to what kind of actress she might be; the fact that her headshot/pinup photo is blue suggests that her films might be equally blue.  (This no doubt eluded radio programmers, censors, and my 3-year-old brain when I first heard the song.)
But the song is really about the sum of its perfect parts.  It's the way Fagen's voice sounds against the galloping funk of Rick Marotta's drums and Chuck Rainey's bass; it's Jay Graydon's searing guitar solo, which defies any kind of categorization and comes completely out of left field.  Those elements are the reason why the song holds up to repeated plays instead of being stuck in the boneyard of late 70s R&B.

"Bodhisattva" (Steely Dan)

The opening track from Steely Dan's second album Countdown to Ecstasy (1973) is, in typical Steely Dan fashion, a snarky commentary on pop culture trends of the time.  For one, it's a jab at supposed gurus and self-appointed spiritual leaders.  But it's also poking fun at fadsters who were jumping on the bandwagon of Eastern religious philosophies while wanting a fast track to enlightenment by way of superficial gestures (I'm gonna sell my house in town).
At its heart, it's a blues song, stretched out from a typical 12 to 13 bars.  But its what the band does with those 13 bars that sets it apart from just any ol' electric blooze.
I'll start with Donald Fagen's keyboards.  They're deceptively simple.  At first blush, he just seems to be playing the same two-chord, boogie-woogie pattern, over and over.  But as you listen, you realize he's playing some pretty complex cluster chords that are akin to something Billy Strayhorn would have written for Duke Ellington.
But most notable is the guitar solo by Denny Dias.  It's not specifically a jazz solo, but it's also not squarely in the realm of rock either.  It's like Django Reinhardt reinterpreting Danny Cedrone's solo from Bill Haley's "Rock Around the Clock."
Even though it isn't Steely Dan's best known song, it's one of the band's best moments.