Album #4: The Rolling Stones, ‘Exile on Main St.’

If this isn’t the greatest rock-and-roll album ever recorded, it’s pretty damn close. Disdained at the time of its 1972 release, “Exile on Main St.” today is regarded as the Rolling Stones’ best work — a chaotic double-record set comprising a few classic songs and a jumble of bits and pieces. There’s a lot of filler on “Exile” — but it’s great filler.

Now for a controversial assertion: “Exile” is not only the Stones’ best album, but it’s so much better than anything else they’ve done that you’re left gaping in wonder. I’ve said that about two other albums on the list — Derek and the Dominos’ (i.e., Eric Clapton’s) “Layla” (No. 6) and Van Morrison’s “Astral Weeks” (No. 12). But I think most people would agree with me in those cases. Making that same argument about any album by the Rolling Stones, though, flies in the face of classics like “Beggars Banquet” (1968), “Let It Bleed” (1969) and “Sticky Fingers” (1971) — not to mention the live “Get Yer Ya-Ya’s Out!” (1970), my second-favorite Stones album, largely on the strength of Keith Richards’ amped-up guitar.

Well, I’ll stick with it. Mick Jagger has a reputation for being a control freak, and the other albums, for all their raw power, are just a little too perfect. “Exile,” largely recorded while the band members were literally tax exiles holed up in France, is right on the verge of veering out of control, more Keith than Mick. Not to glorify drug use, but Richards had a raging heroin habit at the time, and that led to some weird lineups, such as guitarist Mick Taylor playing bass on “Tumbling Dice” instead of Bill Wyman.

Let me linger on “Tumbling Dice” for a moment, because I think it’s the Stones’ single greatest song — which is saying a lot. It opens with a classic Richards riff and features a gospel choir, supposedly inspired by Jagger’s attending the concert at which Aretha Franklin performed the songs that became her album “Amazing Grace” (No. 22). There are little touches that kill me every time I hear them. Charlie Watts marking time during the outro, only to come crashing back in. Keith’s now-you-hear-him-now-you-don’t harmonies. Mick’s wail seguing perfectly into a slide guitar. Something magical and desperate was captured that night. I’ve only seen the Stones once, but I’ve listened to “Tumbling Dice” on several live albums, and it’s flat and uninspiring by comparison. That’s really saying something for a band whose songs usually sound better live than in the studio.

Beyond that, it’s hard to pick favorites. “Rocks Off” for the great line “The sunshine bores the daylights out of me.” “Happy,” maybe Keith’s best vocal performance. “Hip Shake,” “Casino Boogie,” “Torn & Frayed,” “Turd on the Run,” “Ventilator Blues,” “Just Want to See His Face” — what we used to call deep album cuts, with a ragged, not-quite-finished quality. “Black Angel,” “Loving Cup,” “Let It Loose” and “All Down the Line” are all melodic and beautiful while still rocking hard.

The Stones recorded some fine albums after “Exile,” most notably “Black and Blue” (1976) and “Some Girls” (1978). And they’ve remained an excellent live band, not to mention a vibrant cultural force well into their 70s. From “Satisfaction” to their COVID song, “Living in a Ghost Town,” they have been a welcome presence in our lives for more than 50 years.

On “Exile,” though, they achieved something higher: transcendence.

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Album #5: McCoy Tyner, ‘Enlightenment’

I knew right away what I wanted to play Sunday morning as I thought about the life and death of Ruth Bader Ginsburg. McCoy Tyner’s “Enlightenment” is one of three spiritually intense albums on this list, and it’s the one that speaks most directly to me. Recorded live at the Montreaux Jazz Festival in Switzerland in 1973, it consists of four great musicians addressing the Almighty in as direct a way as you are likely to hear in this plane of existence.

Tyner, who died earlier this year, was one of the leading pianists of the 20th century. He was, among other things, a key player in John Coltrane’s classic quartet — the one that recorded “A Love Supreme” in 1964. I imagine Tyner saw “Enlightenment” as his own answer to “A Love Supreme” — and, truth be told, he doesn’t quite manage to equal Trane’s towering accomplishment. Who has? But I’m going with Tyner because I was introduced to “Enlightenment” when I was a teenager, and thus it resonates with me in a way that goes beyond “A Love Supreme.”

How to describe “Enlightenment”? It’s impossible, really. The bare-bones rundown is that the album comprises the three-part “Enlightenment Suite” plus three additional tracks — “Presence,” “Nebula” and “Walk Spirit, Talk Spirit.” Tyner is all intensity and dense chords. The other musicians, saxophonist Azar Lawrence, bassist Joony Booth and drummer Alphonse Mouzon, are collaborators rather than accompanists — full participants in a common purpose.

Booth’s solo between “Nebula” and “Walk Spirit, Talk Spirit” is astonishing. At the beginning, he sounds like he’s groping for something that’s eluding him. But then he finds it, and what he plays is the closest to singing that you’ll ever hear on an upright bass. Much of the concert is available on YouTube; here are parts one and two. They are well worth watching to get an idea of the level of concentration and sheer physical effort that the band brought to bear.

(By the way, the other spiritually focused albums on the list are Van Morrison’s “Astral Weeks,” No. 12, and Aretha Franklin’s “Amazing Grace,” No. 22.)

I had the good fortune of seeing Tyner perform twice in the 1970s, at Paul’s Mall and the Paradise. He was a great soul whom we’ll all miss, but he left a legacy that will endure. I know that Justice Ginsburg’s tastes tended toward opera. But I’m sure she would recognize the brilliance and the connection to the infinite that Tyner, Lawrence, Booth and Mouzon made in Switzerland one day 47 years ago.

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Album #6: Derek and the Dominos, ‘Layla and Other Assorted Love Songs’

There are three albums on my list that are what you might call black-swan events — they are so much better than anything else the performer recorded that all you can do is gape in awe. One of them is Van Morrison’s “Astral Weeks” (No. 12). Another is yet to come.

Today’s entry is Eric Clapton’s greatest moment as a recording artist. “Layla and Other Assorted Love Songs” is better than what he did with Cream and, sadly, far better than anything from his long, mostly disappointing solo career. Released in 1970, “Layla” is perhaps the ultimate guitar album. Clapton has never sounded better, pushed to unequaled heights by guest guitarist Duane Allman, who contributes stinging slide guitar. Solos are double- and triple-tracked; it can be hard to tell who’s playing what.

Clapton has always been obsessed with the blues, and he is at his best on “Nobody Knows You When You’re Down and Out,” “Key to the Highway” and especially “Have You Ever Loved a Woman” — all of which are grounded in an authenticity that’s utterly lacking from his derivative 1994 all-blues album, “From the Cradle.”

The title song, with its famous piano coda by drummer Jim Gordon (or perhaps, as I learned in researching this post, Rita Coolidge), is considered by most observers to be the best on the album. But it’s suffered from overexposure during the past 50 years, and I actually prefer some of the rave-ups co-written by Clapton and organist Bobby Whitlock. Songs like “Anyday,” “Keep on Growing,” “Tell the Truth” and “Why Does Love Got to Be So Sad?” are so drenched in guitar heroics by Clapton and Allman that you feel spent just listening to them.

The vocals, by Clapton and Whitlock, are on one level some of the worst ever committed to tape; on another level, though, they add to the feeling of over-the-top chaos that pervades the entire album and makes it so exciting to listen to. Unfortunately, though the original vinyl struck me as bright and well-produced (by Tom Dowd), the CD I later bought and now the Spotify version sound muddy, even though it’s supposedly been remastered. The crystalline sound I remember from my teen years doesn’t quite come through.

“Layla” ranks a little lower here than it did on my Facebook list because the idea on Facebook was to list the albums that most influenced your music tastes. Here I am simply ranking my favorites — and as outstanding as “Layla” is, I’ve got five I like more.

Derek and Dominos only recorded one album and came to a bad end. Whitlock, like Clapton, is still with us and continues to work. But Allman died in a motorcycle accident. Bassist Carl Radle died from alcohol and drug abuse. Gordon, a terrific drummer, murdered his mother during a psychotic episode and was sentenced to life in prison.

For one brief moment, though, they made magic together.

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Album #7: Carla Bley and the Jazz Composers Orchestra, ‘Escalator over the Hill’

There are three albums on my list that I discovered because of great music writing. The first, Charlie Parker’s “Bird/The Savoy Recordings (Master Takes),” comes in at No. 14. Another will come later.

Today’s entry is “Escalator over the Hill,” a two-hour 1971 release written by Carla Bley and performed by her, the Jazz Composers Orchestra (which she co-founded) and a cast of stars. I discovered this remarkable album because of a review by Stephen Davis that appeared in either The Phoenix or Boston After Dark; I suspect it was the former, though I didn’t make a note of it on the clip that I kept. (For you alt-weekly trivia buffs, Boston After Dark became The Boston Phoenix, and The Phoenix became The Real Paper. It’s complicated.)

Davis describes “Escalator” as “a phantasmagoria of sound, imagination, and virtuousity,” and Bley’s writing as “a mingling of the immediacy of rock with the harmonic and thematic intelligence of jazz.” What music-obsessed 15-year-old could resist? Especially since you could order the three-record set, with notes, pictures and “a handsome gilt-letter box,” for just $12, not a lot of money even then.

“Escalator” was No. 5 in my Facebook list earlier this year. I’ve moved it down a bit. Great as it is, it’s just not the sort of thing I find myself listening to very often. It’s too big, too ambitious. The music comes at you relentlessly, in waves. How to describe it? A jazz-rock opera? (Or, rather, a jazz and rock opera; there is no jazz-rock on “Escalator,” thank you very much.) A “chronotransduction,” as Bley calls it?

I listened to “Escalator” in full this week for the first time in a few years. It doesn’t merely hold up. It sounds as fresh as it did when it was first released. The 13-minute “Hotel Overture” is as stunning a piece of music as I’ve heard, a gonzo big-band performance that ranges from a rather traditional opening to free jazz, anchored by Gato Barbieri’s screeching tenor sax.

And there’s so much more. Much of it is indescribable, but I should note that, among some of the finest jazz musicians of their era, we also get to hear Linda Ronstadt, nearly unknown at the time; Jack Bruce, a couple of years past Cream; and Viva, part of Andy Warhol’s entourage, who provides occasional narration with an utter emotional flatness will make you laugh.

A word about Bruce: He’s all over the album, and his singing and bass playing are among the highlights. Davis called “Escalator” “the zenith of Jack Bruce’s long and amazingly checkered career.” You could also say that Cream was not the best power trio Bruce ever played in; rather, it’s Jack’s Traveling Band on “Escalator,” in which he’s joined by Mahavishnu John McLaughlin on guitar and Paul Motian on drums (and Bley on organ). “Businessmen,” in particular, rocks so hard that there’s really no place else to go.

I could go on. But let me express my one reservation: Paul Haines’ maddeningly obtuse lyrics. Depending on my mood, I find them either hilariously inventive or hopelessly pompous and esoteric. The story is supposed to be about the weird characters who inhabit Cecil Clark’s hotel, set in Rawalpindi. But it really isn’t. Bruce and Ronstadt supposedly play the lead characters, David and Ginger — but that idea is haphazardly executed at best. Here’s a taste of Haines from “Detective Writer Daughter”:

Detective writer of English
She was once the queen of Sweden.
His father’s horse was something like a house
Dad was a German where they lived.

But never mind the lyrics, although you might love them. This is incredible music that stands up to repeated listenings — oom-pah music, Indian music, ominous noise, trumpeter Don Cherry’s atonal soloing, chanting.

I started with Stephen Davis. I’ll close with Marcello Carlin, who began a 2003 essay about “Escalator” with this: “So here I am, faced with the task of explaining and justifying to you the piece of music which I regard as the greatest ever made, the gold standard against which I qualitatively measure all other music, the definitive record which, 30 years after its original appearance, may still render all other records redundant.”

The greatest record ever. How can you resist? Oh, and did I mention that, for all its strangeness, “Escalator” is also surprisingly accessible? Set aside some time and give “Escalator over the Hill” a chance. Everything else is melancholy and industrial.

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Album #8: The Nitty Gritty Dirt Band, ‘Will the Circle Be Unbroken’

During a long reporting trip to Washington and Baltimore in 2002, I began listening to WAMU, which at that time played a lot of bluegrass — not the sort of thing I normally liked (or so I thought). But as I was driving around from interview to interview, I started to enjoy what I was listening to. After I got back home, I started listening to the WAMU internet stream on occasion.

That led me to check out  the Nitty Gritty Dirt Band’s 1972 album “Will the Circle Be Unbroken,” a 38-song compilation starring some of the great bluegrass and old-time country stars of the 1940s, ’50s and ’60s. As this Wikipedia article explains, many of these folks’ careers were on the decline, supplanted by the slick Nashville sound that eventually morphed into (God help us) contemporary country music. By contrast, there is a real sense of authenticity to “Circle,” an album of traditional music about God, death and heartbreak, with a backdrop of virtuoso playing by guitarist Doc Watson, banjo player Earl Scruggs and fiddler Vassar Clements. Many of the songs are instrumentals, and the musicianship is so stunning that it sounds like bebop from an alternate universe.

The album cover is a real period piece, depicting the American and Confederate flags and a picture of an unnamed military officer. Obviously that would never fly today. But in the ’70s, there was still quite a bit of Confederate nostalgia infecting the culture, and the Nitty Gritty Dirt Band — a country-rock band from Southern California — was not immune. Around the same time, the Band was recording “The Night They Drove Old Dixie Down,” an ode to the Confederacy that was an enormous hit for Joan Baez, just to give you an idea of how pervasive it was.

Of all the guest stars on “Circle,” my two favorites are Mother Maybelle Carter, from the original Carter Family, and Roy Acuff, who leads on two of the strangest, most intense songs on the album. “The Precious Jewel,” which Acuff wrote, is a weeper about a young love who’s gone on to her reward in heaven. “Wreck on the Highway,” written by Dorsey Dixon, and first recorded by Acuff in 1942, is even wilder. Here’s a taste:

There was whiskey and blood all together
Mixed with glass where they lay
Death played her hand in destruction
But I didn’t hear nobody pray

Acuff’s singing is a revelation — a ragged, full-throated yowl that stands in contrast to the polite vocalizing on most of the album. Bruce Springsteen was so impressed by “Wreck on the Highway” that he wrote a completely different song by the same name — one of his finest, which captures the bleakness of its predecessor if not its weird mixture of piety and violence.

Maybelle Carter was a member of the first and second iterations of the Carter Family as well as the mother of June Carter Cash. She’s the only woman on the album, and her participation gives the entire project the feel of a last roundup. She takes the lead on “Keep on the Sunny Side,” “I’m Thinking Tonight of My Blue Eyes,” “Wildwood Flower” and, of course, “Will the Circle Be Unbroken.” She also plays autoharp, which isn’t something you hear much of these days.

The Nitty Gritty Dirt Band itself pretty much disappears on “Circle,” providing little more than some background accompaniment. They released a second volume in 1989 that fails to recapture the magic despite the presence of Johnny Cash and John Prine. A third, released in 2002, is better, and features the likes of Alison Krauss, Willie Nelson, Iris DeMent, Emmylou Harris, June Carter Cash, Johnny Cash and Dwight Yoakam as well as old standbys Doc Watson, Earl Scruggs and Jimmy Martin.

Oh, and you can still listen to Bluegrass Country. I had it tuned in Sunday morning, when they played several hours of gospel music by the Stanley Brothers.

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Album #9: Al Green, ‘Greatest Hits’

For those of us on the younger end of the baby boom, the great male soul singers came along a little too early. Otis Redding, Wilson Pickett, Sam and Dave, Sam Cooke et al. were integral parts of the 1960s. We’re children of the ’70s. But we had Al Green.

Starting in the early ’70s, Green recorded an extraordinary series of singles. It seemed like he was never off the radio during the first part of that decade. And why would anyone have wanted him to be? Green wasn’t a shouter like some of his predecessors; his voice was more delicate, weaving in and around the song, soaring into the upper register with ease and then back down again. Aretha Franklin may be the greatest singer of the past 75 years, but Green is my favorite. Most of his best moments are on “Greatest Hits,” released in 1975 and repackaged several times since then.

Could anyone hit a snare drum like Al Jackson Jr.? It may seem like a small thing, but there was a particular sound that Jackson got from his drum set, especially the snare, that instantly stamped those songs as Al Green songs. The band was as good as Jackson, and together they created magic.

The list of hits on “Greatest” is overwhelming, starting with “Tired of Being Alone.” President Obama memorably covered “Let’s Stay Together.” Probably my favorite is “L-O-V-E (Love),” which was released in 1975, as Green’s religious side was coming to the fore. Like a lot of Green’s best work, it’s kind of weird. it starts off as a typical love song, and then morphs into something else entirely:

I can’t explain this feeling
Can’t you see that salvation is freeing
I would give my life for the glory
Just to be able to tell the story
About love

You want more weird? Listen closely to his 1973 hit “You Ought to Be with Me,” which includes the line “You oughta be with me until I die.” The key word in the song is “die,” which he stretches out to form its own soaring one-word chorus. Yes, you’ve heard the song a bunch of times, but were you paying attention?

The 1995 CD re-release of “Greatest Hits” expanded the number of tracks from 10 to 15, adding “L-O-V-E (Love)” and “Love and Happiness,” originally part of “Greatest Hits Vol. 2,” and “Belle,” which he released just before he entered the ministry. For some reason, Spotify’s version harks back to the LP, so I’ll have to put together a playlist.

Green could be prickly. In an appearance on “Saturday Night Live” during his ’70s heyday, I remember him getting angry and calling out his band for some perceived offense. Then, in 2012, we had the privilege of seeing him in Portsmouth, New Hampshire. He was in fine voice and put on a terrific show. But at one point he complained to the audience that the promoter had wanted him to perform for more than an hour. I don’t think any of us thought that was an unreasonable request.

Green can be temperamental, but there are moments that are so perfect that you’re left breathless. If you go to YouTube, you can find two versions of Green singing the Sam Cooke civil-rights classic “A Change Is Gonna Come.” The first, from the 1995 concert for the Rock and Roll Hall of Fame in 1995, is, well, OK. He was clearly having a good time.

The second, from the 2001 United We Stand concert after 9/11, is transformative. Dressed in white, Green is completely serious, a picture of concentration and passion, encapsulating his art into five minutes of anguish and release. It is an astonishing performance.

As one of his albums proclaimed, Al Green is love.

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Album #10: ‘Lyle Lovett and His Large Band’

I’m not exactly sure when I first heard “Lyle Lovett and His Large Band,” Lovett’s third album, but it was surely within a year or so of its 1989 release. For a long time I thought his fourth album, “Joshua Judges Ruth” (1992), was his best. But I relistened to both before writing this post, and though I love both albums, “Large Band” is the one that sticks with me.

It’s also the album that remains the backbone of his live shows. The Large Band is an old-style Texas swing band. Their musicianship is impeccable. If you think Lovett’s albums tend to be overproduced, you really need to go to a concert. These musicians are every bit as good and precise in person as they are on record. And they swing.

As for the album itself, it’s divided into two halves, as albums sometimes were before CDs and streaming. Side A is with the full band, and if I have a complaint, it’s that it doesn’t sound much like Texas swing; it’s more like the big-band music your grandparents listened to. That said, the songs are terrific. “Here I Am” (“If it’s not too late, make it a cheeseburger”) and “What Do You Do/The Glory of Love” (a duet with Large Band stalwart Francine Reed) are staples of his concerts.

Side B is all country, including his cover of “Stand By Your Man” (included in the movie “The Crying Game”) and songs that have become Lovett standards, like “I Married Her Just Because She Looks Like You,” “If You Were to Wake Up” and “Nobody Knows Me.” Lovett’s range consists of about three notes — but he knows how to make the best of his limitions, sounding sly or heartbroken depending on what the song calls for.

Starting with “Joshua Judges Ruth,” Lovett expanded into gospel, and the Large Band more explicitly embraced Texas swing. An especially good example of the latter is “That’s Right (You’re Not from Texas),” which is on “The Road from Ensenada” (1996).

Lovett is one of those rare talents who drove me to get all of his albums. I’ve heard almost every one of them, and each has something to offer. My wife and I have seen him three times, all in outdoor venues — the last in August 2017 at a winery near Rockport, Maine. The highlight of that show came near the end, when he brought on a gospel choir he’d bused in from Boston and performed a lengthy gospel set.

Lovett always comes across as humble and grateful for the opportunity to make a living from music. His songwriting may have faded, but he remains a vibrant, relevant performer. We’d go see him every summer if we could.

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Album #11: John Prine, ‘The Missing Years’

As with Tom Waits, Van Morrison and a few of the others on this list, I didn’t tune in to John Prine until his career was well under way. In 1991, songs from his remarkable album “The Missing Years” began popping up on the radio, and I liked them enough to buy the CD. It is a wonderful piece of work, warm, funny and wistful, showing off Prine at his best.

The title was in part a play on Prine’s five-year absence from recording — but it also echoes the last song on the album, “Jesus The Missing Years,” a hilarious meditation on what Jesus may have been up to during all those years between childhood and his public ministry. But that song is a trifle — the rest of the album consists of more substantial fare, alternating between solo acoustic songs and full-band workouts. The highlights are “All the Best,” “The Sins of Memphisto,” “Take a Look at My Heart,” “Everything Is Cool” … actually, everything on the album is pretty great.

“The Missing Years” was Prine’s first album since the death of his longtime friend and producer Steve Goodman. Howie Epstein, the bassist in Tom Petty and the Heartbreakers, lent Prine a crisper, more pop-oriented sound without sacrificing any of Prine’s rootsiness. Epstein also brought in a raft of guest singers, including Bruce Springsteen and Bonnie Raitt. Unfortunately, Epstein’s hack tendencies came to the fore on Prine’s 1995 follow-up, “Lost Dogs and Mixed Blessings,” which has some fine songs but is marred by a generic rock sound. (It does have the greatest album cover of all time.) Prine recorded only sporadically after that.

Prine was something of a legend from the beginning of his career in the 1970s, when he was hailed as a “new Dylan” — like so many others, including Springsteen. I had long been smitten with Bonnie Raitt’s version of his song “Angel from Montgomery.” “The Missing Years” sent me back into Prine’s catalog. But though he was a strong songwriter right from the start, I’d argue that “The Missing Years” is his best album. His singing, thin and unattractively smug when he was in his 20s, had mellowed into something deeper and more empathetic. And though the young Prine was justly celebrated for wise-beyond-his-years songs like “Hello in There,” he was also capable of cranking out a nasty piece of work like “Donald and Lydia,” which cruelly mocks two young losers for no discernible reason. By contrast, “The Missing Years” is the work of someone who sounds like you’d enjoy having a few beers with to discuss the meaning of life.

In poor health for many years, Prine died of COVID-19 back in April. We were fortunate enough to see him perform in Boston in 2018; he was in surprisingly fine voice and in even finer spirits. If you get a chance, check out his two albums of duets with female singers on classic country songs, “In Spite of Ourselves” (1999) and “For Better, or For Worse” (2016). Also worth a listen is his final album, “The Tree of Forgiveness” (2018), his last collection of original songs.

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Album #12: Van Morrison, ‘Astral Weeks’

As far as I was concerned, Van Morrison was just a voice on the radio. I liked some of his stuff, not all of it. I wasn’t motivated to buy any of his albums. If I had to describe him, I’d have said he was, well, OK.

But I’d heard about an album he’d made near the beginning of his career that never got played on the radio and that supposedly established him as a genius on the order of Bob Dylan or the Beatles. So on the same day in 1990 that I was picking up Tom Waits’ “Franks Wild Years” in the used-CD bin at Tower Records, I decided to take a chance on Morrison’s “Astral Weeks.”

Released in 1968, “Astral Weeks” is mostly acoustic jazz/folk/rock with a first-rate band anchored by the bassist Richard Davis. It is an intensely spiritual record, explicitly on the title track, implicitly on the rest. The melodies are simple and repetitive, giving Morrison’s singing — improvisational and heartfelt — plenty room to stretch out. Morrison supposedly didn’t like the strings that were added later, but I disagree.

I’m nothing but a stranger in this world
I got a home on high
In another land
So far away
So far away
Way up in the heaven

The most fully realized songs on “Astral Weeks” are the title track, “Cypress Avenue” and “Madame George,” which transport you — as Morrison sings — to “another time, in another place.” Overall, “Astral Weeks” is so much better than anything else Morrison recorded that you are left in awe, wondering where it came from. And we’re talking about a musician who’s recorded many fine albums over the years.

There’s a wild backstory to it as well. Morrison wrote and rehearsed much of the album while in Cambridge and Boston while in hiding amid a nasty dispute over the rights to his recordings following his big 1967 hit, “Brown Eyed Girl.” Ryan Hamilton Walsh wrote it up for Boston magazine in 2015; he later expanded it into a book.

“Astral Weeks” is a gift from above.

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Album #13: Tom Waits, ‘Franks Wild Years’

My earliest exposure to Tom Waits was in the 1970s, when I saw him on television performing “Step Right Up.” He struck me as an obnoxious hipster, and I paid little attention to him for many years.

Then, in 1990, I was browsing through the used CDs at Tower Records and came across Waits’ “Franks Wild Years,” as well as No. 12. I was in the midst of getting over a bad period in my life, and something about “Franks” appealed to my dark side. I hadn’t heard any of the songs. Maybe I had read something about it.

It proved to be a smart decision. “Franks Wild Years,” which came out in 1987, was the soundtrack for a play that disappeared not long after its debut. It features outrageous percussion, a pump organ that sounds like something you’d hear on a 1930s radio drama, accordion, sound effects (including a rooster that, as I later learned, turns up on just about every Waits album) and Waits’ otherworldly singing, with seemingly a different voice for every song. Waits wrote every song either solo or with a collaborator; his wife, Kathleen Brennan, shares credits on three and Gary Cohen on one.

At the time that I first listened to “Franks,” I was also reading William Kennedy’s “Ironweed.” There was a certain synchronicity between the boozy losers whose personae Waits adopted and those whom Kennedy wrote about. Waits truly inhabits his characters. He’s also a hopeless romantic, and songs like “Innocent When You Dream,” “Franks Theme” and “Train Song” are suffused with depth and humanity.

After that, I picked up a few more Waits albums. I remember that, sometime in the mid-1990s, WRKO Radio was bringing in guest hosts on Sundays, and I got the call one week. They asked me what I wanted for bumper music. They told me I could pick anything within reason — not, you know, Tom Waits, ha ha. Well, as a matter of fact … I asked for the instrumental that opens “Goin’ Out West,” from “Bone Machine” (1992). It’s pretty straightforward, so I got my way.

And may I just say that “Georgia Lee,” from “Mule Variations” (1999), is probably the most heart-breaking song I’ve ever heard. The bridge will bring you to your knees.

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