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Playlist: Bob Dylan’s most epic songs

Bob Dylan performs in California, 2009. (Kevin Winter/Getty Images for AFI)

Turning 80 this month, Bob Dylan has certainly had an epic life. He’s also written some epic songs — and we mean epic. Although he kept things pretty concise at the beginning of his career, Dylan soon began to draw on the folk tradition of long story songs, putting his own surreal touch on the genre. He’d often run long when he was collaborating, writing about a real person, or both; in his late career, Dylan likes to use long songs to punctuate his albums at their conclusions.

Running 158 minutes despite having only 16 tracks, our playlist of Bob Dylan’s most epic songs is one to turn to when you’re really ready to settle in and let the Nobel-winning singer-songwriter take you on a journey. Let’s begin, shall we?

“With God On Our Side” (The Times They Are A-Changin’, 1964)

This iconic anti-war song marked the first instance of Dylan leaning hard into expansive repetition; like many of his later epic songs, it’s historically oriented. From the colonial slaughter of Native peoples to the weapons of mass destruction that loomed over the Cold War, Dylan walks through a litany of societies that have believed they had a divine sign-off on the taking of human life.

“Ballad in Plain D” (Another Side of Bob Dylan, 1964)

Fifty years before Solange let Jay-Z have it in an elevator, Bob Dylan got an earful from Carla Rotolo, an artist and the sister of his soon-to-be-ex-girlfriend Suze Rotolo — star of his Freewheelin’ album cover. Proving that “epic” isn’t always a good thing, Dylan wrote this bitter ballad about the confrontation: “Beneath a bare light bulb the plaster did pound/ Her sister and I in a screaming battleground/ And she in between, the victim of sound.” Not the nicest number in Dylan’s catalog (“I must have been a real schmuck to write that,” he said in 1985), “Ballad in Plain D” is nonetheless notable for its lilting melody and its foreshadowing of Dylan’s later long breakup songs.

“It’s Alright, Ma (I’m Only Bleeding)” (Bringing It All Back Home, 1965)

A towering, harrowing litany of apocalyptic violence, “It’s Alright, Ma” was one of the three songs Dylan played solo at his 30th anniversary concert celebration in 1992: a cold splash of water on the nostalgia-drenched Madison Square Garden audience. One of the song’s lines seemed particularly apt on that occasion: “He not busy being born is busy dying.” An indictment of mid-1960s culture, the song has become a touchstone of Dylan’s catalog; versions of the song appear on several of his live albums.

“Desolation Row” (Highway 61 Revisited, 1965)

“Sad-Eyed Lady of the Lowlands” got a lot of attention for taking up the entire fourth side of Blonde on Blonde, but “Desolation Row,” from Dylan’s preceding album, was actually a longer song — clocking in at 11 minutes and 21 seconds. It became a template for later epic tracks, with lyrics suggesting a bleak journey through a desperate and lonely landscape, laid over a soundscape both ominous and poignant. Some listeners have taken the lyrics describing “postcards of the hanging” while “the circus is in town” as a reference to a 1920 lynching in Duluth; the victims were employed with a traveling circus.

“Sad-Eyed Lady of the Lowlands” (Blonde on Blonde, 1966)

One of multiple classic Dylan songs about his wife Sara Lownds, “Sad-Eyed Lady” is the culmination and climax of Blonde on Blonde, the album acclaimed by many as the artist’s most singular achievement. Despite the apocryphal reference in Dylan’s later song “Sara” (“Stayin’ up for days in the Chelsea Hotel/ Writin’ ‘Sad-Eyed Lady of the Lowlands for You'”), the song was in fact written in a Nashville recording studio. To this day, Dylan has never performed “Sad-Eyed Lady” in concert.

“Lily, Rosemary and the Jack of Hearts” (Blood on the Tracks, 1975)

Although it’s the longest song on Blood on the Tracks, “Lily” is also the sprightliest, a welcome change of pace in an album full of raw emotions and pained accusations. One of the album tracks recorded in Minneapolis, this Western saga is so cinematic that it’s inspired two unproduced screenplays.

“Joey” (Desire, 1976)

Even the eight-and-a-half-minute “Hurricane” sounds like a Magnetic Fields song compared to this sprawling biography of mobster Joey Gallo. A Jacques Levy co-write like most of the songs on Desire (Dylan later said the lyrics were entirely Levy’s), “Joey” was controversial for how sympathetically it treated a mob hitman, and most critics consider it among Dylan’s lesser efforts, but Dylan himself has described it as “Homeric.” That word is telling: for Dylan, the myth of “Joey” may be more important than the man.

“No Time to Think” (Street-Legal, 1978)

“Talk about a masterclass in phrasing,” wrote a fan of this song in a devoted Reddit thread. “You want to give yourself a challenge, try singing this one in the shower sometime.” It’s true; for all the devoted Dylan fans out there, it seems unlikely to the point of vanishing that anyone’s actually managed all nine verses of this monster in the shower, at least not without laminated lyrics.

“Jokerman” (Infidels, 1983)

“Jokerman” isn’t the longest song on this list; in fact, it’s not even the longest song on Infidels, Dylan’s return to (mostly) secular themes after his gospel trilogy. The mid-tempo reggae-tinged single isn’t particularly weighty in a musical sense either, but lyrically it punches above its weight. The identity of the eponymous “Jokerman” is as elusive as that of Mr. Jones from “Ballad of a Thin Man”; an official video featured images of Ronald Reagan, Muhammad Ali, Adolf Hitler, and…Bob Dylan. Bolstering his Caribbean cred, Dylan got quite a compliment from Wyclef Jean, who called this song “the most incredible piece of literature I ever read.”

“Brownsville Girl” (Knocked Out Loaded, 1986)

Knocked Out Loaded is up there with Self-Portrait among the most reviled studio albums of Dylan’s career (an unkind critic suggested the title must have referred to the way the album was made), but “Brownsville Girl” received special consideration as a collaboration with Sam Shepard. Like “Lily, Rosemary and the Jack of Hearts,” it draws strongly on narrative Western themes; in this case, the narrator muses back on a Gregory Peck movie that he doesn’t precisely remember, since the plot he describes draws on elements from multiple Peck films.

The actor returned the compliment in 1997, paying tribute to Dylan at the Kennedy Center Honors. “Dylan was singing about a picture that I made called The Gunfighter,” said Peck, “about the lone man in town with people comin’ in to kill him and everybody wants him out of town before the shooting starts. When I met Bob, years later, I told him that meant a lot to me and the best way I could sum him up is to say Bob Dylan has never been about to get out of town before the shootin’ starts.”

“When the Night Comes Falling from the Sky” and “Series of Dreams” (The Bootleg Series Volumes 1-3, 1991)

The first Bootleg Series box set was one of the most consequential releases in Dylan’s catalog, prompting a wholesale rethinking of his legacy and setting a new bar for archival releases. He chose these two tracks to end the set, with the first fading into the second to underline their status as a diptych. Taken together, they can be heard to tell the story of Dylan’s evolution from the apocalyptic preacher of the early ’80s to the grizzled observer who emerged in full force on 1989’s Oh Mercy.

Why was the latter track, which might have been hailed as the best song on that album, left off? Producer Daniel Lanois argued strongly for it, and his prickly working relationship with Dylan might have led to Lanois’s advocacy having the opposite effect. In the end, its destiny as the climax of a sprawling three-disc alternate history of Dylan’s career might have been the best possible outcome.

“Highlands” (Time Out of Mind, 1997)

An epic song at an epic turn in an epic career, “Highlands” might be the one song included on this playlist if there was only room to include one song. In an album filled with stunningly evocative autumnal reflections, “Highlands” closes the proceedings on a restless note, cementing Dylan’s late-career persona as a lost prophet. He even manages to work in a priceless dark comic exchange in a restaurant encounter with a server who says, “You don’t read women authors, do you?” Fair question.

“Ain’t Talkin'” (Modern Times, 2006)

This rambling nine-minute dirge, which closes Modern Times, is very much in the vein of “Highlands.” It’s even more darkly tinged, though, with a malevolent air that reminded critic Andy Greene of Cormac McCarthy’s The Road and put Jacob Nierenberg in mind of the same author’s No Country for Old Men.

“Tempest” (Tempest, 2012)

In the past decade, Dylan’s returned to the historical thread that’s stretched throughout his career — and particularly through the songs on this playlist. “Tempest,” his third-longest song (after “Highlands” and “Murder Most Foul”), chronicles the sinking of the Titanic, a contemporary classic shipwreck song in good company with “The Wreck of the Edmund Fitzgerald” by Gordon Lightfoot, who Dylan concisely inducted into the Canadian Music Hall of Fame in 1986, calling him “a rare talent and all that.”

“Murder Most Foul” (Rough and Rowdy Ways, 2020)

Amidst all the horrifying developments of the past year, certain artists seemed to realize that we needed them. Dua Lipa released a transcendent pop album; Bruno Mars and Anderson .Paak debuted Silk Sonic; and Bob Dylan just started randomly dropping new original songs, including this one, the longest of his career. A pained recounting of JFK’s assasination, it became a cornerstone of Dylan’s 39th studio album. Does he have even longer songs in store? Never, ever put it past him.