I’ve been writing a lot about Bob Dylan recently. So much so that some friends are starting to advise – “Jon, stop writing so much about Bob Dylan.” I can take constructive criticism.
So in this rundown of seven sensational artists who crafted runs of five consecutive outstanding albums, I’m not including Dylan. Despite the fact that his run from 1964’s Another Side of Bob Dylan to 1967’s John Wesley Harding reinvented modern folk music, transforming it from acoustic protest music into electric personal exploration, I will not mention him.
Now that I have succeeded in not mentioning Dylan, I can move on.
Best five-album runs in music history
Five straight excellent albums is hard. Really hard. Just ask Mick and Keith. If Brian Jones hadn’t forced them to do Their Satanic Majesties Request in 1967, they might have had nine or ten consecutive first-rate discs, but alas, it was not to be. (It’s impossible to actually number the Stones' early releases because of the overlapping UK and US editions. That’s another reason to leave them off this list.)
So I’m looking for runs in the modern pop era that boast five excellent albums. Not perfect albums. There can be a misstep or two. But the vast majority of the material on each release must be outstanding.
And I’ll admit right up front, I’m looking to broaden the musical map here. So even though there are a couple of obvious, big-name choices included, I went in search of different genres and different time periods, You know, I’m trying to move beyond Hibbing, Minnesota, and a certain singer-songwriter who some people claim I dwell on too much.
I mean, I like all kinds of music. Doesn’t really matter the genre, as long as it’s good. And there is good – sometimes great – sometimes five-album-run great – music in all genres. As we are about to see…
MILES DAVIS
Milestones (1958)
Porgy and Bess (1958)
Kind of Blue (1959)
Workin’ (1960)
Sketches of Spain (1960)
Of all the artists on this list – indeed, of all the artists in the canon of post-war western music, no one put out as much outstanding music in as compressed a timeline as Miles Davis. You could easily jump ahead a decade to the vital rock and blues fusion music from the late ‘60s and find an even more incendiary run of albums. But I don’t go back and listen to Bitches Brew these days.
I do listen to these albums, centered around the groundbreaking Kind of Blue, which many critics have identified as the most important jazz album ever released. This particular run features an astonishing array of musical styles and performers. Because recording dates and release dates don’t always coincide on Davis’s albums, these albums also show off the transition from his original quintet with John Coltrane on tenor sax to the modified sextet with the addition of Cannonball Adderly’s alto sax. You can hear that new energy from the very first track of Milestones, “Dr. Jekyll”
From there, he shifted direction with his adaptation of Gershwin. His frequent collaborator Gil Evans arranged the American classic for Davis’s sextet, supplemented by other horns and woodwinds for a sound that was both orchestral and free-flowing.
On the other side of Kind of Blue, we get a throwback to the original quintet with top-tier compositions by Coltrane and Dave Brubeck, before closing the run with the exceeding beauty of Sketches of Spain, another Gil Evans collaboration, which closes with “Solea,” one of Davis’s most towering achievements.
THE BEATLES
Rubber Soul (1965)
Revolver (1966)
Sgt. Pepper’s Lonely Heart’s Club Band (1967)
Magical Mystery Tour (1967)
The Beatles (The White Album) (1968)
As with the Rolling Stones, the different releases in the UK and USA make this a little tricky. The run above is actually not accurate for either country but does capture the new music that the lads put out between 1965 and 1968. And I figure even if you want to quibble and toss Yesterday and Today or Yellow Submarine into the mix, the run still holds up.
Rubber Soul changed rock & roll forever, allowing it to become more expressive and deeper than anything that came before. “Drive My Car” still rocked, but “Girl” ached in a more mature way than rock had previously managed.
Revolver is the greatest album from the most important band in the history of rock & roll. It is simultaneously psychedelic and classical, while still rocking.
Sgt. Pepper may have suffered from being overly praised. It is a stretch to call it the first concept album in rock history, though it is clearly the most significant. You can believe it is overrated while still being an excellent collection of songs.
The American release of Magical Mystery Tour is the forgotten album. It featured music from their worst film, and has one or two pointless tracks like “Flying.” But it also has titanic numbers like “The Fool on the Hill” and the underrated George Harrison composition “Blue Jay Way” on side one.
Side two features a couple of non-album singles that rank among the band’s most beloved songs – “Strawberry Fields Forever” and “Penny Lane.” In the middle of it all, we get “I Am the Walrus,” which points the way toward The White Album, an astonishing collection of musical ideas. Some of them fall entirely flat like “Wild Honey Pie” and “Revolution 9.” But there is so much to love that it washed those occasional missteps away.
STEVIE WONDER
Music of My Mind (1972)
Talking Book (1972)
Innervisions (1973)
Fulfillingness First Finale (1974)
Songs in the Key of Life (1976)
When Paul Simon won the Grammy for Album of the Year for 1975’s Still Crazy After All These Years, he made a point of thanking Stevie Wonder for not releasing an album that year. That’s how dominant Wonder was in the mid-70s. Rank these five albums in whatever order you like – they constitute the greatest five-album run in modern pop music history.
It’s not as if they came out of nowhere. Wonder was a child prodigy who had been cranking out hits for Motown for a decade. Music of My Mind revealed an adult artist writing love songs with extraordinary sophistication for a 21-year-old. “Superwoman” and “Happier Than the Morning Sun” feature equal parts youthful excitement and old-soul wisdom.
Less than a year later came the extraordinary breadth of Talking Book. With its twin poles of “You Are the Sunshine of My Life” and “Superstition,” the prodigy was living up to his promise and redefining what popular music could do.
The three remaining albums simply continue that expansion. From the political “You Haven’t Done Nothin” from Fulfillingness… to the towering double album Songs in the Key of Life, Wonder was in rarefied air. That double album was highly anticipated because it was the first time in a while he had taken a little bit of time between releases. And it did not disappoint.
I can’t say anything that would do justice to the centerpiece of this run. Innervisions is one of the greatest albums in the history of American popular music. Listen to it. That’s my only insight.
BRUCE SPRINGSTEEN
Darkness on the Edge of Town (1978)
The River (1980)
Nebraska (1982)
Born in the USA (1984)
Tunnel of Love (1987)
Springsteen has the greatest first eight albums in all of rock & roll and the only real question is which five to choose. I’m skipping the first three so that I can end with Tunnel of Love, his most underrated album. That means excluding the huge breakthrough – Born to Run – which landed him on magazine covers and proved to the world that of all the “new Dylans,” this was the one who would carve out his own remarkable path.
Darkness is tortured – both in its songs and in its production. But the results are overwhelming. The River was his first number-one album and yielded his first top-ten hit - “Hungry Heart.” It may be the weakest of the albums in this run, but that’s only because it is the only double album, and there is naturally going to be a little bit of filler.
Springsteen didn’t succumb to the impulse to release his next two discs as a double album. Though much of Born in the USA was composed at the same time as Nebraska, Springsteen and producer Jon Landau correctly recognized that half of his new songs were best suited for a lone voice and guitar, while others needed a full-out band treatment. Nebraska became his most personal and influential recording. Born in the USA became his monster hit. Tunnel of Love is as deep, mysterious, and heartfelt as any rock album examination of love is likely to get.
HUSKER DU
Everything Falls Apart (1983)
Zen Arcade (1984)
New Day Rising (1985)
Flip Your Wig (1985)
Candy Apple Grey (1986)
Hardcore and post-punk bands from the 1980s had a hard time sustaining success. Whether it was due to poor promotion or interpersonal dynamics that scuttled many of the best bands of the era, it may have been harder to crank out five great punk albums than it was in any other genre. That’s what makes Husker Du’s achievement so remarkable.
The first album here was released by Reflex, a creation of the band itself. It was the equivalent of self-publishing, punk rock style. The final album was for Warner Bros, the mountaintop for aspiring bands. In between, they released the middle three for SST, Greg Ginn’s iconic indie – arguably the most important indie label in American rock & roll. As they moved on, the band’s style changed some, but the quality remained intact.
Husker Du avoided some of the pitfalls bands encounter when cranking out material by having a pair of excellent songwriters. Guitarist Bob Mould and drummer Grant Hall generally shared songwriting duties from Zen Arcade onward. Bassist Greg Norton helped out as well.
The debut is rough and sloppy but its take on Donovan’s “Sunshine Superman” shows the promise of what is to come. Zen Arcade picked up the challenge thrown down by SST labelmates Minutemen by creating a massive double album that aimed far higher than the band had up to that point. New Day Rising and Flip Your Wig are the best examples of the shift from noise to melodic hardcore that any band achieved in the mid-‘80s.
The move to a major label, which got them branded as sell-outs by many punks fans, produced some of their greatest individual songs. Hart’s “Don’t Want to Know if You Are Lonely” may well be their greatest single.
THE CHICKS
Wide Open Spaces (1998)
Fly (1999)
Home (2002)
Taking the Long Way
Gaslighter (2020)
At the risk of venturing into some contentious culture-war waters, I’ll go out on a limb and say the band once known as The Dixie Chicks produced one of the greatest three-album runs in country music history between 1998 and 2002. After that, their story gets more complicated as they both won and lost fans due to political statements and an examination of what country music is and isn’t. It seemed for a long while that the trio had said their goodbyes with 2006’s Taking the Long Way. Then, Gaslighter appeared and it was as if the 14-year hiatus had not even happened.
The Dixie Chicks existed prior to 1998, but they didn’t have Natalie Maines as their lead singer. They had been an up-and-coming country/bluegrass quartet before the lineup shift. Maines' voice is immediately dominant on the opening tracks of Wide Open Spaces – both the title track and the proudly possessive “I Can Love You Better.” And the toughness of “Let ‘Er Rip” foretold of women who were not going to wilt in the face of controversy.
The follow-up, Fly, smashed all records and made the trio the biggest stars in country music. The romantic beauty of “Cowboy Take Me Away,” and the romantic reality of “Goodbye Earl” pretty much covered as much ground as two songs could on the subject of love.
Home is a gorgeous album. It has rugged rockers and the tenderest of love songs. It should have teed them up for long-standing dominance in both country and pop. Then came Maines' comment on American foreign policy.
I won’t rehash the story – look it up if you don’t know it. Everyone has an opinion on what she said. The effect was to derail their careers – at least for a while. Taking the Long Way was the thoughtful, passionate rejoinder to those who attempted to put them down. They may have lost some old fans, but the album went double platinum and swept the big three Grammys in 2007.
It seemed as if that was the end of the Chicks’ story and that they would not get to that fifth album. Then they teamed up with super-producer Jack Antonoff for Gaslighter, which drew on all their past styles to create one more sensational country-rock-pop hybrid. Who knows what may be next?
BEYONCE
4 (2011)
Beyonce (2013)
Lemonade (2016)
Renaissance (2022)
Cowboy Carter (2024)
OK – an admission. I don’t think I knowingly listened to a Beyonce song prior to 2016. Eventually, the hype surrounding Lemonade got to me and I gave it a spin. I was chagrined. I don’t like being forced to accept that I am often so much of a snob that I write off modern pop. But I’m learning.
The key album here – which, as you now know I didn’t listen to until it had been out about five years – is 4. It is probably the weakest album on this list but it is still vital. Not only does it have a lot of great songs, from stone-cold rockers like "Schoolin' Life" to the heartache of "I Care," but it also reveals an artist willing to take on different challenges. It was well known that Beyonce had moved on from her father as manager for this release. There’s a freedom on 4 that is palpable. It also leads to a bit of an eclectic mess, but that’s a small price to pay for what you get in return.
What we get in return is a string of four extraordinary albums. Not that she really needed it, but Beyonce, with its surprise release and a bevy of hard-hitting tracks, proved she was the biggest star in the industry. Then she topped it with Lemonade. Musically, culturally, and politically – it is among the most important releases of the new century.
It took six years before her next album, in part because of COVID and in part because of her desire to take a deep dive into the way race figures into her music. She had already established with Lemonade that racial roots would no longer be something to gloss over in order to achieve mainstream pop success. By Renaissance, it was something to revel in and glorify. I am still learning about all the touchstones, but I can listen to the Afrobeats of “Move” or swing between the musical seesaws of “Church Girl” and “Alien Superstar” and simply buy into the groove.
Then Cowboy Carter once again rewrote the rulebook. There’s something to be said for being revolutionary. When you marry that revolutionary spirit with supreme craftsmanship, it results in a great album. Or in this case, 35 great albums from seven vital artists. Not one of them named Bob Dylan.

