Right—the holidays are over, the Christmas tree is fuel for the fire, and the worst of the NYE champagne bottle shards have been swept up; it's time to get serious. As in, resolutions.

Over the past few months I've been trying to listen to more jazz. I can't quite remember what started this whole project, but now I won't rest until I've achieved my own transcendental jazz trance.

As it so happens, while checking out the local flea market recently I chanced upon some very relevant box sets, comprising some fifty classic jazz albums.

So here's the plan: at one album per week, that gives me about a year of autodidactic jazz education, plus a buffer at the end for some self-reflection. I don't have a textbook or any other proper guide; I'm just going to listen to the albums, binge some Wikipedia pages, and see where that gets me in a year.

Fair warning: this post is just going to be me brain-dumping my uneducated, undiscerning thoughts on these albums. I don't imagine it will be entertaining or useful in any way for literally anybody else, but hey, you're the one reading it. If, for some misguided reason you do want to follow along, there's a dedicated feed for just this project in addition to the overall blog feed, as well as a separate section of the site.

Week 1: Louis Armstrong Plays W. C. Handy

Not really knowing anything about these box sets in advance, I embarked on this project with some trepidation that I had signed myself up for fifty weeks of crap. By the end of this album's first track, I was a believer.

The top-notch musicianship and Satchmo's¹ trademark gravelly crooning are already reason enough to listen, but I can't emphasize enough how much fun this album is: the frequent banter between Louis and Velma Middleton is charming, and the whole thing is joyous and downright raucous throughout. I mean, just listen to this laugh:

One thing I don't understand: W. C. Handy was the "Father of the Blues," and most of the songs here have "blues" in the title—obviously there's lots of shared heritage between jazz and blues, but where exactly does that dividing line lie? And what is this exactly?

Favourite track: St. Louis Blues

Week 2: Sarah Vaughan in Hi‐Fi

This one is a slower burn for me: obviously Sarah Vaughan is an incredibly talented vocalist, but this doesn't quite get my blood pumping like the last album; sometimes her melodies go a little too all over the place for my taste. That said, I'd gladly put this on for a nice romantic dinner (skip "Mean to Me" in that case, though).

Also, apparently Miles Davis is playing the trumpet for most of these tracks? We'll get back to him soon enough…

Favourite track: Nice Work If You Can Get It

Week 3: The Jazz Messengers

After Ms. Vaughan's lovely but somewhat sedate tunes, I was hoping for this week to bring a little more energy, and The Jazz Messengers definitely delivered on that front. Wikipedia tells me we're in hard bop territory now, and it's not hard to hear why it might've earned that moniker.

Art Blakey is undeniably a monster on the drums, but some of his solos end up sounding a little… samey to me? Take the first big solo from Infra-Rae: it starts to get repetitive for me in a way that I've never felt when listening to say, Neil Peart. Listen for yourself and see if you agree:

Not too much more to say on this one, other than that I'm glad to have some high-tempo, vocal-free jazz—good music for when you really need to get something done. Oh, and "Carol's Interlude" on this album really reminds me of "Epistrohpy" from another Monk/Coltrane album I have.

Favourite track: Hank's Symphony

Week 4: Lady in Satin

Given that the primary feature here is a solo female vocalist—Billie Holiday—I couldn't help but compare this album to the earlier Sarah Vaughan album. I prefer this one: the lush orchestral backing really helps create a sweeping, dramatic sense of romance, as opposed to Vaughan's lighter, airier mood.

Immediately, one can hear some fragility and rasp in Holiday's voice; she comes across as much more "mature" than Vaughan to my ears. What I hadn't realized was the sad explanation: at the time of the recording, Holiday was in poor health, after having weathered decades of damage from alcohol, hard drugs, and abusive relationships. She recorded this album in February 1958 and passed away barely 18 months later. The critical consensus seems to be that the album packs a huge emotional punch, but that Holiday had lost some of her range and force by this point—I'd like to return to her earlier work and compare for myself.

I suspect this album will also hold a special place in my heart owing to the circumstances of my first listen: not wanting to miss a week, I had copied this album to my phone in advance of a trip to the Netherlands; I listened to it together with my wife on the train as we watched the Dutch countryside go by.

Two miscellaneous closing thoughts:

• It's a dang shame that she never had a chance to sing a Bond theme (and not only because that would up the Billie–Bond count to two).
• Thanks to Wikipedia, I learned that there's a crater on Venus named after her.

Favourite track: For Heaven's Sake

Week 5: Kind of Blue

We're into the heavy hitters now—this is one of the few jazz albums I picked up prior to this experiment, based on its universal praise. What is there for me to say that hasn't already been said? It's Kind of Blue—if any album is jazz, it's this one.

From what I've been able to gather online, Kind of Blue is notable for pioneering modal jazz (in response to hard bop). My limited understanding is that in hard bop, melodies were largely driven by quick chord progressions: soloists displayed their incredible virtuosity by continually adapting to the rapidly shifting tonal centre dictated by the chord changes. In contrast, modal jazz uses very few, slow-moving chords—giving soloists more latitude to develop their melodies without being constrained by the strictures of the chord progression. (As for what exactly musical "modes" are and what their significance is, I still don't have a clear understanding.)

I'm sure I'll be listening to and learning from this one for many years to come, along with the rest of the world.

Favourite track: So What

Week 6: Time Out

This album was an immediate revelation for me. I've listened to some great stuff already, but Time Out had me hooked from the first few bars—the opening rhythm of Blue Rondo à la Turk is now permanently tattooed on my brain. Perhaps that's no coincidence; Time Out's primary innovation is its usage of time signatures that were previously uncommon in jazz (e.g., ⁹ ₈ in Blue Rondo à la Turk; ⁵ ₄ in Take Five). If, like me, you're struggling to understand the nuances of ⁹ ₈ rhythm, here's a helpful explanatory video from Wikipedia:

Got it? Good.

Another thing that stood out to me was how… classical this album sounds? Even on my first listen, something here struck me as familiar in a way I hadn't experienced with the earlier albums.

One more embed before we go: Canadian film animator Steven Woloshen produced a short film set to Take Five that I think is pretty neat:

Favourite track: Blue Rondo à la Turk

Week 7: First Time! The Count Meets the Duke

As previously mentioned, I had listened to a grand total of three jazz albums before setting out on this expedition. We've already encountered Kind of Blue; one of the other two was Side by Side—Side by Side was mostly a Johnny Hodges album, but they stamped his better-known bandleader Ellington's mug on the cover, presumably to juice the sales.

I bring all of this up because this week's album features some of the same suspects: Ellington has gathered together his big band (Hodges included), but they're not alone: Count Basie—another big band luminary—is on set with his crew, and out to wage Big Band "Battle Royal" (sic)! The stereo mix is intended to capture the conflict: Basie's group is heard on left channel, while Ellington's is on the right.² To my undiscerning ear, the result sounds as cooperative as it does antagonistic, but that doesn't stop it from being a blast through and through. At peak moments, the brass can get a little screechy; I don't think it's ever over the top but my wife is not on board with it. (E.g., listen to the climax of Battle Royal—it's on the verge of cacophony, but I think it remains on the "impassioned finale" side of the line.)

I've bandied about "big band" above with any proper explanation, so I suppose I ought to fill in some of those details: big band is exactly what it sounds like—a musical ensemble for jazz that consists of at least ten (and often 17 or more) musicians (usually divided into saxophones, trumpets, trombones, and rhythm). Compared to earlier jazz ensembles (which typically comprised 4–5 musicians), big bands were obviously larger, but also had a greater focus on written compositions (owing to the increased difficulty of coordinating solos across a much bigger group). Big bands reached peak popularity in the late 1930s/early 1940s alongside "swing," the subgenre of jazz they usually played. Swing was very popular at dance halls; as you might guess from the name, it features a "swinging" rhythm (usually by accenting the second and fourth beats). Both Duke Ellington and Count Basie were both highly regarded big band leaders who shaped the development of swing (Ellington in particular was also a prolific composer and arranger).

tl;dr:

Big band

Jazz group of at least ten musicians (probably more).

Swing

Subgenre of jazz with a strong emphasis on a "swinging" rhythm; frequently played at dance halls.

Favourite track: Wild Man (aka Wild Man Moore)³

Week 8: Parole E Musica

Eight weeks in, and we've arrived at a dubious honour: this is the first album where the top-billed performer (Helen Merrill in this case) is still alive—as I write this in February 2025, she's a sprightly 95 years old according to Wikipedia. Perhaps more excitingly, we've also got our first duplicate track: we first heard "You Don't Know What Love Is" in week 4 (I give the edge to Merrill).

This album has an interesting gimmick. For each "song," there's two tracks: the first is a spoken word version of the song's lyrics in Italian; the second is the real song (with Merrill singing in English). Is it completely unnecessary and self-indulgent? Yes. Do I love it, and does it make me pretend I'm living on the Amalfi Coast in Ripley? Also yes.

Also, this is the third album to feature a lovely leading lady, and I have a confession to make: while there's no denying the sublimity of Merrill's singing, it's pretty clear to me by now that this isn't what I want out of my jazz—I'd almost always sooner reach for any of the instrumental albums we've heard, or Armstrong's bombastic vocals.

One final bit of trivia for the week: this might be the first you've heard of Helen Merrill, but you surely know one of her son's songs: he wrote the original version of "I Love Rock 'n' Roll."

Favourite track: Why Don't You Do It Right

Week 9: Tijuana Moods

Charles Mingus was another one of those "big names" from the jazz world that I recognized, but had never actually listened to until this week. Tijuana Moods sounds quite different than anything else we've heard so far; I'd describe it as more assertive and even a bit combative at times (though smooth elsewhere; e.g., on "Flamingo"). This certainly isn't "easy listening;" compared to the other albums it feels less eager to please the listener and more experimental—maybe it's fair to call it a concept album? As you might've guessed, the album was inspired by Mingus' time in Tijuana; throughout the album, even my ignorant ears can clearly discern the Latin beats and motifs getting the blood pumping as the jazz takes off.

But the track that's stuck with me the most isn't even from the original release of the album. "A Colloquial Dream (Scenes in the City)" was only added on some later CD releases: it's nearly 11 minutes long and merges jazz with spoken-word poetry; it features a down-on-his luck narrator recounting his love for jazz and his struggles living in Harlem. At first, I didn't like it, and I wasn't convinced it was likeable by anyone—a fun novelty, sure, but is this still even music? But after listening to the album all week long, propinquity did its thing, and that narrator now lives rent-free in my head (a good development for him given his situation with the landlady). This isn't the kind of song you can blast at the gym or put on your party playlist, but if you're in a ruminative mood—possibly with a dram of whisky in hand—there's a real depth of soul here.

Now catch this… DIG!

Favourite track: A Colloquial Dream (Scenes in the City)

Week 10: Chet Is Back!

Ooh, this sounds pretty different to me than what we've heard so far. I think that's mostly due to the appearance of electric guitar in a few tracks and more prominent bass throughout—it strikes me as more "modern" overall? The song that most captured my attention was "Ballata in forma di blues," written for the album by Amedeo Tommasi (who also plays piano on the album); something about that starting chord progression had me completely transfixed. Interestingly, almost none of the other songs on the album were original compositions. They're almost exclusively covers, including a Thelonious Monk track (remember that name) and that perennial favourite, Over the Rainbow.

After eight instrumental tracks, I wasn't expecting the vocals on the last four (all sung by Baker himself). There's a good reason for that—those four tracks weren't on the original album release; they were a series of "orchestral pop tracks" that Baker later recorded with Ennio Morricone. (Yes, that Ennio Morricone.) Regardless, they've got a calm charm of their own that complements the more upbeat earlier tracks. I'm glad they were added for this CD reissue.

As for Chet Baker the man, he seems to have been the poster boy for everything your high school's anti-drug program said would happen—with his boyish good looks and multifold musical talents, surely the world was young Chet's oyster! Unfortunately—like many of his contemporaneous jazzmen—Chet developed a heroin addiction early in his career and spent the rest of his life in and out of jail. He died at age 58 after apparently falling out of a hotel window while high.

As if that wasn't sad enough, Wikipedia's biography of Chet includes the sentence "Baker was an irresponsible and distant father," with a footnote. Dear reader, I will be a father myself soon, and while I am sure I will make more than my own fair share of mistakes, I'm hoping not to foul it up to the point that it's citation-worthy.

One more obligatory random connection. Remember when I said that listening to Parole E Musica made me feel like I was in Ripley? Turns out I was a couple of weeks early—in the 1999 movie The Talented Mr. Ripley (based on the same source material as the 2024 miniseries), Matt Damon impersonates a Chet Baker recording.

Favourite track: Ballata in forma di blues

Week 11: Monk's Dream

Moms didn't dig [jazz], she just didn't go for it

Bird, Miles, and Max… she couldn't see it

Morning, afternoon, night, or anytime

That is, until I played her some Monk one night, late

'Round about Midnight time

I played her some Monk!

—Thelonious, that is

And now Mom spends many of her nights in Tunisia

—"A Colloquial Dream (Scenes in the City)"

I suppose you can tell that Thelonious Monk is a big name given that I've already alluded to him three times so far before actually getting to one of his own albums.

In retrospect, I can see that I came to this album with misplaced expectations. Knowing how revered Monk is and that this is one of his best-known albums, I was expecting something more avant-garde—something challenging and foreign; something that had moved jazz as a whole forward. Instead it's a… very fun and dare I say approachable listen? If someone wanted to dip their toes into jazz, this seems like a pretty reasonable recommendation to me.

Everything that I've read about Monk mentions his idiosyncratic approach to piano—his percussive attacks on the keys, "angular" melodies, and emphatic use of dissonance and silence. I'm still too much of a neophyte to discern those in any sophisticated way; I can hear the dissonance come through in places (particularly in "Body and Soul"), but I doubt I could pass a blind "is it Monk?" test.

Perhaps the above makes it sound like I'm down on the album, which isn't the case. There's a lot of fun and whimsy here; I particularly like the scratchy sax in "Bright Mississippi" and the main jaunty melodic line it features. "Bye-Ya" and "Sweet and Lovely" also stand out because I know them from an earlier album (not featured in our 50-week journey)—in "Sweet and Lovely" I prefer the halting ritardando ending on Monk's Dream to the chromatic (?) flourishes on the other album.

But overall, I'm leaving this week with a renewed appreciation for Tijuana Moods—I think that's closer to what I wanted Monk's Dream to be. Maybe by the end of this project I'll be able to better appreciate Monk's genius in its own right.

Favourite track: Bright Mississippi⁴

Week 12: Sonny Meets Hawk!

Ah, the saxophone: I'm sure we can all agree, objectively one of the best instruments. And this week we're treated to a sax masterclass: as the back cover helpfully explains, we've got Sonny Rollins ("the 'boss' of modern tenor sax") on the left channel, and Coleman Hawkins ("the father of jazz saxophone") on the right.⁵ These are indisputably two masters of the instrument, live in improvisational conversation with one another, and what a conversation it is.

But first! Since we're on the topic of the saxophone, there's something I positively have to get out of my system. Please enjoy this series of increasingly absurd fun facts that never fail to delight me:

• The saxophone was invented in the early 1840s by Adolphe Sax. So it really just is a "Sax-o-phone." For some reason I always thought it'd be deeper than that.
• But Sax didn't stop at his phone: he also graced us with his saxhorn, saxtuba, and—who could forget?—the dulcet saxotromba. Also, this thing:

• But those pitiful horns could only deafen a man at close range. Sax had greater ambitions: his "Saxtonnerre" (a locomotive-powered… organ?) was designed to be heard all across Paris, without any amplification. (This one never made it past the concept stage.)
• At this point, you might have pigeonholed Sax as a designer of niche instruments. Not so; he was a true renaissance man—when he saw the devastation wrought by prolonged sieges in war, he designed the perfect solution: a cannon so giant that rather than besiege a city, one could simply level the entire city with a single shot. He called it—all together now!—the "Saxocannon." Mercifully, it was never built.⁶

Even by my loose standards, that's a signficant digression. How's the actual album this week?

It's a hoot and a holler! And a times a screech, and also occasionally a… plaintive whine? Point is, there's lots of sounds coming out of the saxophones, including a bunch that I wasn't expecting and a few that frankly I don't associate with competent saxophonists. And yet somehow, it all works? I mean, just listen to this snippet from the end of "Lover Man":

You cannot tell me in good faith that no saxophones were hurt in the making of this album. But you also cannot tell me that their pain was in vain.

Favourite track: All the Things You Are

Week 13: At Newport '63

Enough of this American jazz hegemony! Martial Solal, "an Algerian-born Frenchman who plays more like an American than perhaps any other foreigner,"⁷ is here to show us a European take on jazz.

This album comes to us (mostly) live from the storied Newport Jazz Festival—charmingly, the back of the album explains that since the only festival slot available for Solal was too short for a full album, they pre-emptively recorded a rehearsal sequence and slapped the festival applause onto the end of those tracks "to make for more natural home listening." (Once you hear the same crowd whistling on half the tracks, you can't unhear it.)

Solal covers some well-trod standards in his set (e.g., "'Round Midnight", "Boplicity"), but the one that really caught my attention was an original composition of his: "Suite pour une frise." Don't be alarmed if the title makes no sense to you; as Martial himself put it: "If you don't understand French, I will make George Avakian to translate in the album notes." Avakian comes through, explaining that the piece is "inspired by an actual frieze; not a classical Greek one but a modern one painted on aluminum high on a modern glass-walled building in Brussels." I, however, needed things broken down even further; I had a vague recollection that a frieze is some architectural thing, but Wikipedia's definition—"even when neither columns nor pilasters are expressed, on an astylar wall it lies upon the architrave ('main beam') and is capped by the moldings of the cornice"⁸—left me with more questions than answers.

Allow me to spare you my confusion: if a building has a flat part above some columns, and especially if the flat part has a nice design on it, that's a frieze, more or less. Of course, the natural follow-up question is: can we locate the exact frieze that so inspired Solal? Well, the French Wikipedia page for the song mentions that it was commissioned for the inauguration of a frieze by Ralph Cleeremans (which demonstrated Cleeremans' novel "aluchromie" technique that allowed fixing pigment to aluminum). I was able to track down some general information about Cleeremans' work, and while I'm doubtful it's the exact frieze in question, you can purchase one of his originals for a cool 4000 Euros.

But, ah, back to the song itself: "Suite pour une frise" leaps out of the gates with forceful energy, and it builds tension early on that keeps you on the edge of your seat. There's a couple great sections where the bass takes the spotlight, but above all else, this one puts Solal's virtuosity front and centre. For me, that last ingredient is the key piece here—I deeply love the piano, but spartan jazz melodies on the keys just don't seem to grab me as much as they might on say, a saxophone. I'm a firm believer that if you can't play the prettiest notes, you ought to at least play the most notes, and on that metric, Solal does not disappoint. (Mind you, I'm not saying that the piano is inherently less musical than other instruments, as my wife would have you believe—a mournful Chopin is equally moving as a crooning sax, but I've yet to find the former properly represented in jazz.)

One final note: I love how much humanity a live recording captures. Yes, Solal's rhythms and melodies will continue to bounce around in my head, but so will his charming introductions ("…and now, Thelonious Monk's classique de jazz, 'Round Midnight"). I'm sure that to Solal, those off-hand remarks were an utterly forgettable part of the show, but on this album they can't help but colour the listener's overall perceptions—an unintended improvisation, recorded for posterity.

Favourite track: Suite pour une frise

Week 14: Two of a Mind

After last week's saxophone detox, this week the jazz gods smiled upon me with a double helping. And after fourteen weeks, dare I say we're… learning? Check this out: this week's album features Paul Desmond and Gerry Mulligan. We know Desmond from Time Out—in fact, he composed "Take Five."⁹ Mulligan, on the other hand, enjoyed inspired collaborations with Chet Baker (though sadly Chet is Back! isn't one such example). What's more, the format of this album (two cooperating saxmen with a stereo channel apiece¹⁰) calls to mind Sonny Meets Hawk! from a couple of weeks ago.

My overall impression of Two of a Mind is that it's witty; several of these tracks are full of tongue-in-cheek "gotchas" (which, admittedly, are lost on me). Per Avakian's notes on the back of the album, "they will let you hear just enough of what you might expect to let you know that they know that you know—and then they're off on a wholly fresh idea." Clever, but Desmond & Mulligan haven't made a fool of me—I'm too ignorant to be hoodwinked by their tricks. What's more, the title track is apparently meant to be another oblique musical reference for the true devotees. (Spoiler alert: the answer is front and centre on the album's Wikipedia page.)

That same wit shines through in the track names. Apparently, after hearing the rapid tempo on track 4, one of the audio engineers aptly suggested the title "Flight of the Bumblebee." Judy Holliday (an actress who was hanging out in the control room and would go on to marry Mulligan a year after this recording) retorted "or… Blight of the Fumblebee!"¹¹ Now that is an A+ Spoonerism; a brilliant example of the comedic arts that we seek to advance here at the Simpsonian. Desmond was also known to partake himself: a lifelong womanizer, upon crossing paths with a former girlfriend he remarked "There she goes—not with a whim but a banker" (a Spooneristic allusion recalling Eliot's most famous stanza¹²).

As for the music itself, it's casual, friendly, and coordinated. Desmond's alto contrasts nicely with Mulligan's baritone; their counterpoint is on point.¹³ The electric guitar on "Untitled Blues Waltz" really got me too—there's an instrument that's been in short supply so far, so the extra funk it brings hits all the harder. Even so, I found myself longing for some of the rougher edges from Sonny Meets Hawk!. I can't quite put my finger on why: the best analogy I have is that Two of a Mind is a wonderfully blended Scotch—Desmond's own favoured Dewar's, perhaps—while Sonny Meets Hawk! is my beloved Laphroaig. Many people in many circumstances will prefer the smooth refinement of the former—but sometimes you want a bare-knuckled peat punch just to remind yourself that you're alive.

Favourite track: Untitled Blues Waltz

Week 15: Together Again!

Going into middle school, I needed to pick an instrument for music class. The choice was clear: I could barely get a whimper out of a flute, and my buzzing on the brass was no good, but by God could I wail on the saxophone. My father was only too happy to indulge my affinity for woodwind by purchasing me a… clarinet. Practicality ruled the day: a clarinet, you see, is significantly cheaper than a saxophone, and is just compact enough to be crammed into one's backpack for easy transportation—my father had no sympathy for the fact that I idolized sexy sax man, not Squidward. I've been unpacking that trauma ever since.

It was surprising to me, then, to learn that all of that unpleasantness could have been avoided had someone simply played me this album all those years ago. Goodman is front and centre on the ol' licorice stick, and blows as hard as any another cat on the scene; there's no shortage of sax appeal here. As for the rest of the quartet: there's no bass (sad), but instead we've got double percussion—drums and vibraphone (!)—to lay down a backbone, plus keys to fill everything out.

From the instrumentation alone, this one struck me as antiquated: nothing else we've heard so far emphasizes these particular instruments, and I can't help but find the combination slightly cheesy. Not in a bad way! It's always fun, and it does legitimately go hard, but clarinet and vibraphone sound so wholesome to me; overall it doesn't quite have the same edge as some other things we've listened to.

Am I right in deeming this sound "dated?" Sort of: Goodman's quartet first made it big around 1936, but this particular recording is an attempt to recapture that magic in 1964 (well after the group had split—hence the "again" in Together Again!).¹⁴ Music had changed much in those intervening decades, thanks in no small part to Goodman himself: many consider his 1938 Carnegie Hall concert to be the event that elevated jazz from popular frippery to serious art music. Society had changed as well, and Goodman was involved there too—his racially integrated quartet was highly controversial and nearly unprecedented, but that didn't stop them from touring the South; by all accounts that I've read, Goodman unflinchingly insisted on the equal treatment of all band members at every stop along the way.

I'm not sure what the original reception to this album was in 1964, but I wouldn't be surprised if it mirrored my own: it's lovely music, but also clearly from another time—a long-lost treasure unearthed from a forgotten time capsule. I suppose that's a reputation one only earns by doing something groundbreaking in the first place.

One final thought: while listening to this album, I kept feeling there was some kind of connection I couldn't quite place. By the end of the week I finally pieced it together: the theme from Monsters, Inc. sounds like it could've come right out of a Goodman ensemble (albeit with soprano sax filling in for clarinet). And man, what a bop that theme is.

Favourite track: Dearest

Week 16: It's Uptown

Inside George Benson there are two wolves:

1. the coolest cat you've ever seen, and
2. the softest, most wholesome guy you've ever met.

In "Clockwise" he's laying down a lick on his electric guitar in tandem with the baritone sax, and hoo boy is it tasty. By contrast, "A Foggy Day" is a cover of a Gershwin song originally made popular by Fred Astaire—Benson's up-tempo take on it injects some much-needed pep, but that doesn't make it any less old-timey.

Many of the artists we've heard so far have been singular students of jazz, devoting their entire career to discovering and mapping her many details. Not so with Benson—there's no disputing his jazz bona fides (as evidenced by this album), but he also extensively recorded pop and R&B;¹⁵ many of the 10 (!) Grammys he's won come from those latter two genres. The aforementioned Cool Guy/Nice Guy dichotomy is present in his pop stuff too: in "Give Me The Night" he's about to sweep your girl off her feet and rollerskate¹⁶ her away into the Californian sunset, but in "Never Give Up on a Good Thing," relationship counselor Benson exhorts you to… never break up? (This is somewhat less surprising after learning that Benson is a Jehovah's Witness and is celebrating sixty years of marriage in 2025.)

But back to It's Uptown: this is the first album we've heard that makes the guitar the star of the show. I have mixed feelings about that—it's hard to top the cool factor of a well-placed guitar riff, but I also find that the instrument struggles to evoke a certain mournful or plaintive tone that is so often core to jazz. That being said, the trusty six-string has other tricks up its sleeve. A great example is "Bullfight," where Benson starts by setting up a Latin beat with some dense, choppy rhythmic chords, then effortlessly transitions to the solo melody. Finally, it bears mentioning that although Benson came to fame as a prodigious guitarist, he's a great vocalist as well—I find the lyrics of the selections on this album a bit cheesy, but I'm a fan of the clear, bright tone of his voice.

So until next week, follow Benson's example: be the baddest dude you can while still being a good guy.

Favourite track: Clockwise