Be that as it may, now, 50 years later, there's room for all 3. But I still have Dylan as my #3 rock artist after Frank and the Beatles and frankly I can more readily put together a list of 50 Dylan songs than 50 by the Beatles.
Bob's Top 50 Songs
This is based on his performances.
1. Desolation Row, from Highway 61 Revisited (1965). What an amazing kaleidoscope of images, right from postcards of the hanging, "the circus is in town" and a beauty parlor filled with sailors to the Titanic sailing and lovely mermaids flowing. Then there's "the riot squad they're restless/they need somewhere to go" and "at midnight all the agents and the superhuman crew/come out and round up everyone that knows more than they do" and "when you asked me how I was doing/was that some kind of joke?" Eleven minutes of, well, desolation. Fellini-esque, they said, or influenced by Alan Ginsburg, which Dylan sort of confirmed, saying that "Desolation Row" came from "that New York type period, when all the songs were city songs. (Ginsburg's) poetry is city poetry. Sounds like the city." Al Kooper, who played electric guitar on early takes of "Desolation Row," but not the Highway 61 version, said that "Desolation Row" was Eighth Avenue in Manhattan with its "whore houses, sleazy bars and porno supermarkets." Who, exactly, is the blind commissioner or Cinderella or Ophelia or Dr. Filth or the Phantom of the Opera? I have not even seen anybody willing to hazard a guess.
It has also been reported that the song may refer to the lynching of 3 black men in Duluth, MN, Dylan's birthplace, in 1920. The 3 were employed by a circus that had come to Duluth, and they sold postcards of the 3 bodies hanging from a light pole.
The Highway 61 version was recorded August 4, 1965, with country/folk wizard Charlie McCoy on acoustic lead guitar. An earlier version (July 29) with Kooper on guitar was released on a 2005 collection, The Bootleg Series Volume 7. It's played at a mid-tempo so that there's plenty of space to articulate and for listeners to clearly hear and comprehend the lyrics. McCoy's fills keep the music interesting without getting in the way. The vocal is understated, laconic. When 1 discovers in the final verse that the singer, too, is trapped on "Desolation Row," that seems reasonable. He's not just an on-looker, he's part of the "circus" that he describes.
2. Like A Rolling Stone, from Highway 61 Revisited. Bookends. "Like A Rolling Stone" opens Highway 61, "Desolation Row" closes it. The 2 greatest songs from 1 of rock 'n roll's greatest artists. No wonder Highway 61 rates as the greatest rock 'n roll LP of all-time. Wikipedia says the song "transformed Dylan's career and is today considered one of the most influential compositions in post-war popular music and has since its release been both a music industry and a popular culture milestone...."
It's a song about a girl who "used to dress so fine" but "Now you don't seem so proud/About having to be scrounging for your next meal.... Nobody's ever taught you how to live out on the street/But now you're gonna have to get used to it...." And then the famous chorus: "How does it feel/To be on your own/With no direction home/Like a complete unknown/Like a rolling stone."
But this song, unlike "Desolation Row," it's also about the music, the sensational music. Here, the music gets very much in the way, boldly, spectacularly. Al Kooper, a young and not particularly well-established guitarist, was invited to the session by producer Tom Wilson. However, it was only with Wilson out of the room that Kooper snuck over to the organ and played his now-famous organ filigree. When the track was played back, Wilson objected to the organ part saying Kooper was "not an organ player." Dylan, on the other hand, insisted that the organ be turned up in the mix.
Despite the song's 6 minute length--and the fact that many radio stations therefore would not play the song--it went to #2 on the Billboard charts. Rolling Stone has twice (2004, 2011) put the song at #1 on its list of the top 500 songs of all-time.
3. Jokerman, from Infidels (1983). "Jokerman" is Dylan's latter-day "Desolation Row," a song filled with colorful and provocative imagery: "Standing on the water/Casting your bread/While the eyes of the idol with the iron head are glowing/Distant ships sailing into the mist/You were born with a snake in both of your fists/While a hurricane was blowing...." "Rifleman stalking the sick and the lame/Preacherman seeks the same/Who'll get there first is uncertain."
And then there's that guitar, but this time it's not country-rock of Charlie McCoy, it's the harder-edged rock 'n roll of Mark Knopfler, who also produced. In fact, the band was certainly one of the best ever assembled for a Dylan album--Knopfler and Mick Taylor on guitar, Sly and Robbie on rhythm, Alan Clark of Dire Straits on keyboards. Their polished but driving sound was perfect for "Jokerman."
But mostly there's those lyrics, that vocal. Some said it was Bob's best poetry since Blood on the Tracks.
4. Lily, Rosemary and the Jack of Hearts, from Blood on the Tracks (1975). Blood on the Tracks was only Dylan's 2nd LP to make it to #1 on the Billboard charts. Surprisingly, Planet Waves had been the 1st a year earlier. Highway 61 only made it to #3. Still, I doubt that most people would pick "The Jack of Hearts" as the best song on the record. Most people refer to it as a record about pain and loneliness. You know, "Tangled Up in Blue"and all that. When someone mentioned that this was among his most popular LPs, Dylan once said, "It's hard for me to relate to that.... People enjoying that kind of pain...."
But for me, there it is. The story, which I won't even try to explain, is intriguing, to be sure, and running almost 9 minutes there's many a plot twist and turn to it. But mainly there's the rapid-fire musical setting dominated by a rollicking Hammond B3 sound. It just sucks you in.
5. Love Minus Zero/No Limit, from Bringin' It All Back Home (1965). One of Bob's pretty love songs, maybe the prettiest loviest of them all, utterly free of cynicism. I was surprised in reading up on this song, which was covered by Joan Baez among many, many others, that Dylan never ever recorded another song he wrote and that Baez covered, that being "Love Is Just a Four-Letter Word." This would be more typical of a Dylan love song, and it would be rated right about here if he had ever recorded it.
6. Things Have Changed, single (2000). Written for the movie "Wonder Boys." "I used to care/But things have changed." Absolutely chilling. Great light-rock accompaniment.
7. Subterranean Homesick Blues, from Bringin' It All Back Home. A total breakthrough--his 1st top 40 hit (#39), one of his 1st "electric" songs, and also known for the then innovative "music video." Then there's the rapid-fire lyrics just brimming with alienation ("Twenty years of schoolin'/And they put you on the day shift") and what have now become familiar aphorisms among baby boomers ("You don't need a weatherman/To know which way the wind blows..." "The pump don't work/'Cause the vandals took the handles."
8. Romance in Durango, from Desire (1976). 1 of Dylan's many Westerns. "Hot chili peppers in the blisterin' sun" and etc.
9. Changing of the Guards, from Street Legal (1978). Another cryptic song but filled with provocative images of some medieval war or something. But my attraction is to the odd polka-like, saxophone-inflected music. Another one that just sucks you in with that sound.
10. Just Like Tom Thumb's Blues, from Highway 61 Revisited. Another song in the let-down category. "When you're lost in the rain in Juarez and it's Eastertime too/And your gravity fails and negativity don't get you through.... Everybody said they'd stand behind me when the game got rough/But the joke was on me/There was nobody even there to bluff." I have to say that I am influenced in this ranking by Judy Collins' incredibly beautiful version, this probably wouldn't rate quite this high on its own merits. I said this would be based just on Bob's own performances. OK, so I lied.
11. I Ain't Got No Home, from A Tribute to Woody Guthrie (1972). The tribute was a live concert staged around the time of Woody's death in 1967. Bob plays with the Hawks, and as of 1972 there were very if any recordings available of Bob with the Hawks.
12. Positively 4th Street, single (1965). I always thought of this as "Like A Rolling Stone," Part 2. Another venomous putdown. And for me, having hung out on 4th Street (SE) in Minneapolis quite a bit during my college years, well, that just made this song more real.
13. It Takes A Lot to Laugh, It Takes A Train to Cry, from Highway 61 Revisited. 1st, what a great title for a song, especially 1 in which those specific words never actually appear. Just a straightforward folk-rock song, almost a defining song for the genre. I mean, what would Gram Parsons have done if this song hadn't existed?
14. Simple Twist of Fate, from Blood on the Tracks. Originally from Blood on the Tracks, of course, but Dylan and his band really nailed this one on Bob Dylan at Budokan (1979), and I vastly prefer that version. But either way, has there ever been a more concise but powerful expression of regret than "She shoulda caught me in my prime/She woulda stayed with me."
15. The Times They Are A-Changin,' from The Times They Are A-Changin' (1964). One of Bob's most famous and oft-quoted political songs, and why not? A great distillation of what people were saying or at least hoping.
16. Most Likely You'll Go Your Way and I'll Go Mine, from Blonde on Blonde. If Bob was unhappy about this particular breakup, he didn't quite capture that in this rollicking rocker.
17. When the Ship Comes In, from The Times They Are A-Changin.' Apparently this is about Bob's ship but again it sure feels bigger, like the ship is comin' in for everybody, for the counter-culture, for the young, for the new age. The times they are a-changin' and when the ship comes in they'll really change. That's what I heard.
18. I'll Keep It With Mine, written in 1964, not released until Biograph (1985). The Biograph version was recorded in the Blonde on Blonde sessions. Another version, more stripped-down, almost demo quality but also from the Blonde on Blonde sessions, was released on The Bootleg Series Vols. 1-3 (1991). In fact, there were a total of 12 versions recorded, some of them incomplete. Only the 2 versions mentioned here have been released. "If I can save you any time/C'mon, give it to me/I'll keep it with mine."
19. Chimes of Freedom, from Another Side of Bob Dylan (1964). A litany of injustice--e.g. "For each unharmful, gentle soul misplaced inside a jail"--followed by the refrain, "We gazed upon the chimes of freedom flashing." A lot like "Blowin' in the Wind" in its construction, but performed with a little more anger, a little less certitude that, well, the times are truly a-changin.'
20. It's All Over Now, Baby Blue, from Bringin' It All Back Home. This is often described as yet another breakup song. I don't know. The sense of loss seems to me to be bigger than that. It's not just a relationship that is over. It's everything. It's life as you've known it. And while the overall emotion is sadness, the ending provides a glimpse of hope. "Strike another match, go start anew."
21. Stuck Inside of Mobile with the Memphis Blues Again, from Blonde on Blonde. Trapped! "Now the Senator came down here showing everyone his gun/And handing out free tickets to the wedding of his son/And me, I nearly got busted and wouldn't it be my luck/To get caught without a ticket and be discovered beneath a truck." And "Here I sit so patiently/Waiting to find out what price/You have to pay to get out of/Going through all of these things twice." Then, "Oh mama can this really be the end/To be stuck inside of Mobile with the Memphis blues again." All with that brilliant guitar/organ sound typical of Dylan's best rock 'n roll from 1965 and 1966, a sound that he would actually never again rediscover or recreate.
22. My Back Pages, from Another Side of Bob Dylan. Here Dylan questions political idealism. "Half-cracked prejudice leaped forth/'Rip down all hate,' I screamed/Lies that life is black and white/Spoke from my skull, I dreamed/Romantic facts of musketeers/Foundation deep, somehow.... My guard stood hard when abstract threats/Too noble to neglect/Deceived me into thinking/I had something to protect/Good and bad, I define these words/Quite clear, no doubt, somehow...." And then the famous refrain, "Ah but I was so much older then/I'm younger than that now."
23. Absolutely Sweet Marie, from Blonde on Blonde. Another light rock love song with the famous line, "I'm sitting here beating on my trumpet... And where are you tonight, sweet Marie."
24. Gates of Eden, from Bringin' It All Back Home. This was also the B-side of the single "Like A Rolling Stone" and, so, it was very widely heard. It was probably less widely understood. It is one of the more inscrutable song from a very inscrutable artist/catalog. It is "a nightmarish vision of...corruption and decay," according to 1 source. The imagery was/is tantalizing.
25. Dirt Road Blues, from Time Out of Mind (1997). This is a very unusual Dylan song in that I just like the music, the little country riff that is repeated over and over again. It just sucks you in.
26. Unbelievable, from Under the Red Sky (1990). This was a really fallow period--after Infidels and before Time Out of Mind. But "Unbelievable" actually made it to #21 on the Billboard rock chart. It's a light rocker with lyrics more resigned than critical even of some trends in the contemporary world that Dylan found "unbelievable."
27. I Want You, from Blonde on Blonde.
28. All Along the Watchtower, from John Wesley Harding. The Hendrix version would rate higher.
29. Maggie's Farm, from Bringin' It All Back Home.
30. Tears of Rage, from The Basement Tapes. The Band's version rates higher.
31. It's All Right Ma, I'm Only Bleeding, from Bringin' It All Back Home.
32. Sad-Eyed Lady of the Lowlands, from Blonde on Blonde.
33. Tangled Up in Blue, from Blood on the Tracks.
34. Let Me Die in My Footsteps, from The Bootleg Series, Volumes 1-3 (1991).
35. Just Like A Woman, from Blonde on Blonde. Seriously, this is 1 of Bob's greatest songs. It rates this low just because it is so over-exposed, I guess. I mean, I don't really ever need to hear this song ever again. But, my goodness, at the time it seemed like the greatest thing since sliced bread.
36. Tombstone Blues, from Highway 61 Revisited.
37. This Wheel's on Fire, from The Basement Tapes.
38. Every Grain of Sand, from Shot of Love (1981).
39. Can You Please Crawl Out Your Window, single (1965).
40. A Hard Rain's A-Gonna Fall, from The Freewheelin' Bob Dylan (1963).
41. You're Gonna Make Me Lonesome When You Go, from Blood on the Tracks.
42. Neighborhood Bully, from Infidels.
43. Everything Is Broken, from Oh Mercy! (1989).
44. Mississippi, from Love & Theft (2001).
45. You Ain't Goin' Nowhere, from The Basement Tapes.
46. Lay Down Your Weary Tune, from Biograph (1985). Written and recorded in 1963.
47. Mr. Tambourine Man, from Bringin' It All Back Home. Also over-exposed.
48. From a Buick 6, from Highway 61 Revisited.
49. I Shall Be Free, from The Freewheelin' Bob Dylan.
50. Blowin' in the Wind, from The Freewheelin' Bob Dylan. Over-exposed.
Bob's Best LPs
I'm not gonna review what songs are on each LP so much--I mean, some--but you can look up above for that.
1. Highway 61 Revisited (1965). What else? I mean, his best 2 songs ever, "Desolation Row" and "Like A Rolling Stone" are both here, and almost everything else is a classic. I've always thought this was the greatest rock 'n roll record ever. Rolling Stone magazine even has Sgt. Pepper's rated as the #1 LP of all-time. Like I've said many times, I'm a Beatles guy. But Highway 61 beats Sgt. Pepper's all to shit.
2. Bringin' It All Back Home (1965). And yet I sometimes think this is the better Dylan album. I guess I'd say, though, this Highway 61 is a rock 'n roll record and this is more of a folk record, and I'm a rock 'n roll guy. But what a year, 1965, 2 of the greatest records of the rock era. Wow.
3. Blonde on Blonde (1966). And then Bob followed Highway 61 with Blonde on Blonde. I do think that some of the love ballads here are a bit maudlin, but "Sad-Eyed Lady" works for me and the rockers are terrific.
4. Blood on the Tracks (1975). Probably only Highway 61 is as essential to Bob's legacy. Highway 61 puts him near the top of the all-time lists but this even more than that kept him there when he could have fallen--was falling, for that matter.
5. Infidels (1983). I don't think anybody would dispute that Bob is a bit casual about arranging and producing. His best work has always been when he empowered somebody to exert some control over those aspects of the music. Here it was Mark Knopfler.
6. The Bootleg Series, Vol. 1-3 (1991). Outtakes, alternative and live versions, etc., from 1961 through 1989. And where there are some interesting tunes from the '70s and '80s ("Angelina," "Series of Dreams"), Disc 1 covering 1961 through 1963 is by far the most significant: "He Was a Friend of Mine," "Let Me Die in My Footsteps," "Walkin' Down the Line," "Only a Hobo" and many more had never previously been released.
7. Bob Dylan at Budokan (1979). His best live record ever.
8. The Times They Are A-Changin' (1964).
9. The Freewheelin' Bob Dylan (1963).
10. Another Side of Bob Dylan (1964). These all kinda run together. "A Hard Rain," "The Times They Are A-Changin,'" "My Back Pages," "The Chimes of Freedom," "When the Ship Comes In" stand out, and I'd be hard pressed to tell you which LP any of them were on.
11. Desire (1976).
12. Street Legal (1977). I loved their sound and "Romance in Durango" and "Changing of the Guards" are way underrated among Dylan's output.
13. Live at Carnegie Hall 1963 (released in 2005). There are now several live concert releases from Bob's early days. This seems to be the best and most historically significant (though, see #16).
14. Love & Theft (2001). Can this record really be a dozen years ago? My god. I just liked its sound.
15. The Basement Tapes (1975). Lots of great good humor here.
16. The Bootleg Series Vol. 4: Bob Dylan Live 1966, The "Royal Albert Hall Concert" (1998). Any early electric concert with the Band (the Hawks), and the audience was not pleased.
17. Biograph (1985). The best collection of oldies, outtakes, etc.
18. John Wesley Harding (1967). The 1st "return" to a folkie sound and the 1 that worked the best.
19. Time Out of Mind (1997). Another 1 that just sounds good. Who knew that his genius would end up being keeping a certain rock sound alive--you know, guitar-rock, basically.
20. Tempest (2012). Ditto.
21. Bob Dylan (1962). 50+ years ago. My god.
22. Planet Waves (1974). Not much admired but like JWH it had a nice folkie sound.
23. Slow Train Coming (1979). Not much admired but it had a couple of very nice tunes on it, e.g. "Gotta Serve Somebody."
24. New Morning (1970). Another of those folkie records after the motorcycle accident.
25. Modern Times (2006). Another nice light-rock record.
26. Self-Portrait (1970).
27. Nashville Skyline (1969). This is the "return" that is most widely admired but it left me a little bit cold. I mean, "Lay Lady Lay"? I don't think so.
28. Under the Red Sky (1990).
29. The Bootleg Series, Vol. 9: The Witmark Demos (2010). Recorded 1962-1964.
30. Before the Flood (1974). Live recording also from 1974.
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