Start to Finish: Bob Dylan

This is the second installment of my “Start to Finish” series (the first being the Beastie Boys). Over the course of about 2 months, I listened to Bob Dylan’s entire discography in order (excluding the bootleg series) to get a better understanding of his progression as a songwriter and artist. This consists of 41 albums (35 from the studio, 6 from live performances), spanning 50 years (from his 1962 self titled debut to his latest 2012 album, Tempest). I rated each album and gave some commentary. Each day this week, I’m posting an article dedicated to each decade of Dylan’s career. There has been so much written about Dylan and his discography that I kept it brief. This is just the impressions of a casual fan diving deeper into his discography. If you want a more thorough analysis of Dylan, I recommend checking out these articles in AllmusicWikipedia, or checking out one of the many films or biographies about his life. I put together all the “essential” tracks in my Bob Dylan Essentials Mix on Spotify (or you can go to Spotify to listen to his entire catalog yourself). I also welcome any comments or insights people are willing to share.

The 1960s

Bob Dylan (1962) – Dylan’s debut is heavily inspired by his hero, Woody Guthrie. The songs are rooted in tradition harmonica heavy folk and delta blues. It’s a solid album but one that only hints at his greatness to come. Essential: In My Time of Dyin, Baby, Just Let Me Follow You Down. 6.7/10

Freewheelin’ Bob Dylan (1963) – It’s impressive to think that by his second album and being merely the age of 20, Dylan had already crafted several songs that have gone on to become pop standards. This is the iconic sound comes to mind when people think of Bob Dylan. You can still hear the Woody Guthrie influence but his songs are starting to take the shape of his own voice and style. The whole album is a great representation of his original iconic sound and the era.  Essentials: Blowin In The Wind, Masters of War, A Hard Rain’s A-Gonna Fall, Don’t Think Twice Cause It’s Alright. 8.2/10

The Times They Are A-Changin’ (1964) – Dylan continues the his traditional folk sound but with more emphasis with storytelling and war protest songs. He also starts to incorporate 3/4 time into the mix. A very good and relaxing listen. Essentials: The Times They Are A-Changin, With God On Our Side, Boots of Spanish Leather. 7.6/10

Another Side of Bob Dylan (1964) – As the title of the album indicates, we are starting to see a new approach. This is Dylan’s serious entry into surrealist imagery. A good example of his poet approach is “My Back Pages.” His occasional lisp and off kilter quirkiness on “All I Really Want to Do” reminds me of Modest Mouse’s Isaac Brock. On “I Shall be Free No. 10” Dylan states “You’re probably wondering now what this song is all about,” which may sum up the sentiment of some listeners, who view his songs as puzzles (or even prophecies). Essentials: My Back Pages, It Ain’t Me Babe. 8.4/10

Bringing It All Back Home (1965) – This is the album where Dylan famously turns his back on traditional folk and goes electric. One thing that’s interesting between the LP days versus now is that albums were viewed in two acts. In the case of this album, side one focued on the electric, side two on the folk. This albums combines the stream of consciousness/surrealest style with his story telling/humor style. This is Bob Dylan ultra hip and on the top of his game. One of my all time favorites. Essentials: Maggie’s Farm, Subterranean Homseick Blues, Mr. Tamborine Man, It’s Alright Ma (I’m Only Bleeding). 9.3/10

Highway 61 Revisited (1965) – With this album, Dylan goes further in developing his folk rock style, collimating in arguably his best and most beloved song, “Like a Rolling Stone.” In addition to including electric guitar and drums in his sound, he is also incorporating organ, mandolin, honky tonk piano and others sounds, including roadhouse blues. The result is another classic. My only complaint is I feel he could have used a little more variety in the melodies instead the “talk singing” approach but at this point, Dylan is more concerned with creating a distinct mood with the lyrics and sounds than making the songs catchy. Essentials: Like A Rolling Stone, Tombstone Blues, Ballad of a Thin Man. 8.5/10

Blonde on Blonde (1966) – By this album, Dylan has started to let loose. There are some great grooves  and distinct relaxed feel. The new-orleans-meets-stoner march of “Rainy Day Woman #12 & 35” doesn’t really do it for me but the rest of the album is absolutely amazing. Another masterpiece.  Essentials: Visions on Johanna, Stuck Inside of Mobile with the Memphis Blues Again, One of us Must Know (Sooner or Later). 9.5/10

The Basement Tapes (Recorded 1967, Released 1975) – The story with the album is that Dylan began jamming and putting together demos with the Band (who were his backing band the last few tours) in Woodstock, New York while he was recuperating from a motorcycle accident. The songs were intended as demos to be recorded by other artists and not as an official release. As these demos began circulating, they turned into a much sought after bootleg. It wasn’t until 1975 the they songs were given a proper release. The result is a handful of gems among a loose, raged, and sometimes sloppy jam session. It doesn’t sound like fully conceived album because that’s not what it was. But you can hear the collaborative spirit in the air (The Band sings and writes on a handful of the songs) and fun they must have had arranging these tunes. Essentials: Million Dollar Bash, Katie Been Gone, Bessie Smith, Apple Suckling Tree, Tears of Rage, Ain’t No More Cane, You Ain’t Going Nowhere, This Wheel’s On Fire. 8.1/10

John Wesley Harding (1967) – This is Dylan’s quiet return from exile. Curiously, he set aside the experimenting and variety he has developed the last 4 albums and went with a more stripped down approach, with just acoustic guitar, harmonica, bass and drums. The songs are more storytelling based but lack interesting production and melodies. Essentials: Down Along the Cove, All Along the Watchtower 6.7/10

Nashville Skyline (1969) – After another break, Dylan returned with a country influenced album (appropriately recorded in Nashville). His voice takes on a noticeable different and distinct tone, which isn’t really better or worse, just different and surprising. The songwriting this time around has improved. The songs are upbeat, melodic and concise. The Johnny Cash collaboration on the opening track is great. The peddle steel and lap steel guitars add some interesting and welcome flourishes to the production. This album is fun, refreshing, and sounds like the begging of a new era for Dylan. Essentials: Girl From the North Country, Lay Lady Lay, Tell Me That It Isn’t True 9.1/10


In the 1960s, Dylan established a legacy through releasing a string of critically acclaimed albums; a difficult mark to live up to. The 1970s found Dylan in a state of transition. He released several live albums, a film soundtrack, a few albums considered outtakes, his 70s masterpiece (Blood on the Tracks), became a born again Christian and started a string of gospel albums. He incorporated new instruments into his sound, which tended to change from album to album. Still, It’s obvious there is still a genius at work.

Self Portrait (1970) – While listening to this album, I read review after review which panned the album, describing as a low point or slump in Dylan’s career; his attempt to shed his audience. In my opinion, this is one of his most underrated albums. This is Dylan gone eclectic; his own white album, if you will. The songs have renewed energy, compared to the flat dullness of John Wesley Harding. He tried new production ideas like adding strings, horns, and soulful female backup singers (see opener “All the Tired Horses”, which doesn’t sound out of place in today’s context of the retro Feist/Arcade Fire sound). He mixed things up by including live reinterpretations of some older material and some great new originals. By keeping the songs in the 2-3 minute range, the album keeps an enjoyable pace for a double album. Perhaps if doesn’t have the cohesiveness of some of his earlier albums but it makes up for it in being an enjoyable listen; an album that sounds like he had fun making. Essentials: Let It Be Me, Alberta #1, The Boxer, Take Me As I Am (or Let Me Go), Take a Message to Mary, All the Tired Horses. 8.7/10

New Morning (1970) – After the commercial disappointment of Self Portrait, Dylan quickly recorded and released New Morning. This time around, he blends folk, country, honky tonk, blues, soul, and jazz with mixed results. It’s loose and sometimes a little sloppy at moments. It sounds as if Dylan is searching for his sound. Essentials: If Not For You, New Morning, One More Weekend. 6.9/10

Pat Garrett & Billy the Kid (1973) – This soundtrack to the film of the same name features a more spanish influenced. He occasionally adds banjo and fiddle. Since it was intended for a film soundtrack, it features mostly instrumental but is notable for the inclusion of “Knocking on Heaven’s Door”. Essentials: Billy 4, Knockin’ On Heaven’s Door. 6.5/10.

Dylan (1973) – These are essentially leftovers from the Self Portrait sessions, which Dylan reportedly did not want released. Several of the songs are covers. For some reason, this is considered his worst album and only listenable for hardcore fans. I’m not sure why. I really enjoyed listening to it. It has a pleasent sound and a good variety, an extention of Self Portrait. Essentials: Lily of the West, Mr Bojangles, Spanish Is the Loving Tongue. 7.8/10.

Planet Waves (1974) – Reunited with the Band, Dylan recorded this album in three days. It’s a very natural and comfortable sound for Dylan, which complements his songwriting style well. The arrangements are cohesive and unifed by the band’s folk rock touch.Essentials: Something There is About You, Forver Young, Never Say Goodbye 8.6/10.

Before The Flood (1974) – Live double album with the Band. Most of the songs are given an more upbeat interpertation than the studio recordings. It includes some of the classics from the Band’s catalog. Dylan’s fresh take on “Don’t Think Twice, It’s All Right”, “Just Like A Woman” and “It’s Alright, Ma (I’m Only Bleeding)” sound more along the lines of the folk/punk anthems of Billy Bragg than his original version. Essentials: Lay Lady Lay, The Night They Drive Old Dixie Down, It’s Alright, Ma (I’m Only Bleeding). 8.1/10.

Blood On The Tracks (1975) – This is often cited as Dylan’s comeback album. While the acoustic guitar sounds a little more in the forefront than his past few albums, his singing style does continue in the “belt it out” singing style he showcased in Before the Flood. The songs are catchy and upbeat with the straight forward, concise arrangements, which straighten the songs in the this case. With Dylan’s divorce happening at the time, many of the songs are more introspective and personal than his other work. A solid album of great material and an enjoyable listen. Essentials: Tangles Up In Blue, Meet Me In The Morning, Buckets of Rain. 8.7/10.

Desire (1976) – Most of the tracks are more laid back and slower then the predecessor. Every song features the violin, which is a nice and welcome change. There is also some accordian and a little bit of spanish guitar influence. It’s a good album but lacks some of the variety of Blood on the Tracks. Essentials: Hurricane, Oh Sister, Joey. 7.3/10

Hard Rain (1976) – Dylan decided to release another live album only 2 years after Before the Flood. This album showcases Dylan tendency to re-interpret his own songs live, with mix results. Some of the version are nice, but as a whole this album doesn’t seem to add too much to the catalog. Essentials: One Too Many Mornings, Lay Lady Lay, I Threw It All Away. 5.4/10.

Street Legal (1978) – Dylan sounds refreshed and relaxed. This time around, many of the songs feature saxophone, gospel singers and gospel organ, which works very well with this group of songs. His singing is also a little more understated than some of his recent albums to this point (especially compared to the live albums), which help ground the album and strengthen it. A solid record. Essentials: Changing of the Guards, No Time To Think, True Love Tends to Forget. 8.3/10.

Slow Train Coming (1979) – Dylan’s first album after becoming a born again christian. Lyrically, there are obviously more references to his faith, quotes of biblical phrases (Do Unto Others….), and current events. It’s not too radically different from some of his earlier material (see “Masters of War”).  A big part of the sound of this album is the electric piano and a clean electric blues guitar. Overall, the result is sort of a hybrid of smooth jazz/lounge, blues, and even reggae. The solo piano closer, “When He Returns”, is one of the most moving and heartfelt songs Dylan has ever written; a strong testiment of his faith. Essentials: Precious Angel, When You Gonna Wake Up, When He Returns. 7.8/10.

At Budokan (1979) – His 3rd live album in 5 years. It’s interesting hearing re-interpretations of his own songs, including reggae takes of “Don’t Think Twice It’s Alright” and “Knockin’ On Heavens Door”. Sometimes the combination of violin and saxophone sounds a bit like Dave Matthews Band. I can’t say I always love the new versions but the arrangements this time around (and his singing) are restrained and more pleasant to listen to than they are on Hard Rain. On a production note, I wished they would have mixed the transitions between the songs to flow better so that it doesn’t sound like it’s jumping from song to song. Seems kind of critical for a live album. Essentials: Like A Rolling Stone, Blowin’ In The Wind, Simple Twist of Fate, All Along the Watchtower. 7.3/10.


The 1980s was a not the best decade for Dylan. His songwriting had gone downhill and the production of his recordings molded to fit the times (the embarrassingly over reverbed, synthy sound of the 80s). Luckily, he ended the decade with the Daniel Lanois produced Oh Mercy, an album that showed he still had it in him, as well as signaling the coming of his latter day renaissance era of the 90s and 00s.

Saved (1980) – This album sounds more of what you would expect as a gospel-influenced album from Dylan than what was on Slow Train Coming. The sound doesn’t seem to fit him particularly well and overall, the songwriting isn’t quite up to bar. Essentials: Covenant Woman, Solid Rock 5.7/10

Shot of Love (1981) – With Dylan’s third album since becoming a born again Christian, he’s toned down the more overt spiritual lyrics, striking a balance in expressing his faith and writing music more accessible to a secular audience. The music is an improvement over Saved, following a more traditional bluesy sound with some pleasant soft songs.Essentials: Heart Of Mine, In the Summertime, Every Grain of Sand. 6.9/10

Infidels (1983) – This is cited as Dylan’s return to secular music, although he still throws in some gospel/biblical references from time to time. The songs and production are solid but not especially great. Essentials: Jokerman, I and I, Don’t Fall Apart On Me Tonight 6.5/10

Real Live (1984) – As with Dylan’s other live albums, his current versions of his past songs come with results. The highlights are the solo section of his set and the blues lead guitar parts. All and all, a solid listen but nothing extraordinary. Essentials: It Ain’t Me Babe, Tangled Up In Blue, Masters of War. 6.7/10

Empire Burlesque (1985) – This effort is heavily influenced by the 80s production at the time (massive reverb on the drums, cheesy synthesizers, etc), which makes it sound dated. Even when I try to look past the production, the songs are just okay. We do get some relief at the end with Dark Eyes, a pretty, simple tune which makes a return to the sparse acoustic guitar/harmonica sound that initially made Dylan famous. Besides that, it sounds like Dylan is losing his touch. Essentials: Dark Eyes, When the Night Comes Falling From The Sky. 4.9/10

Knocked Out Loaded (1986) – While still using the now dated 80s production sounds, this album is an improvement over Empire Burlesque thanks to some help with the songwriting (including Tom Petty). There is a little more variety and the album is kept short, which makes for a more interesting listen. Essentials: Got My Mind Made Up, Under Your Spell, Precious Memories. 6.5/10

Down In The Groove (1988) – This is essentially an odds and ends records full of covers and recorded at various times. The production approach is still very 80s and a little campy. There are a few gems in this batch of songs (usually the softer ones) but for the most part, pretty mediocre. Essentials: Death Is Not The Death, Rank Strangers To Me. 4.6/10

Dylan & The Dead (1989) – This sounds like a great idea on paper but the result of this live collaboration with the Grateful Dead is bland, uninspired interpretations of some of Dylan’s standards. The guitar and keyboard parts do not blend well. It sounds like too many chefs in the kitchen. Essentials: Knockin’ On Heaven’s Door 3.4/10

Oh Mercy (1989) – Dylan sounds very fresh here. He put aside the cheesy 80s production in favor of more direct sound. The record has a great atmosphere with flourishes of tremolo guitar and restrained blues. He’s also written a great batch of solid and direct songs and his voice has never sounded better. The result is his best album in years.Essentials: Ring Them Bells, Man In The Long Black Coat, Disease of Conceit 8.3/10


The 90s found Dylan constantly touring, continuing his work with the Traveling Wilburys, and recording folk covers. He went about 7 years without releasing new material. “Time Out of Mind” became his comeback album, which brought him back in the spotlight and ushered in his critically and commercial successful 2000s material.

Under The Red Sky (1990) – It sounds like Dylan used his best material for Oh Mercy and put the leftovers on this album. The songs sound uninspired and the production is boring. Perhaps he was trying to make a light, “fun” record but in my mind, Dylan sounds best when he is going for depth. Essentials: Under The Red Sky, God Knows 6.2/10

Good As I Been To You (1992) – Dylan’s traditional folk record. This is a refreshing sound, getting back to his sparse roots of just him and a guitar. Although Dylan didn’t write any of these tunes, he makes them his own. There is quite a bit of finger picking, which is great but it occasionally sounds like Dylan has a hard time keeping up with himself. Still it’s a relaxing and charming listen. Essentials: Blackjack Davey, Hard Times, Froggie Went A-Courtin’ 7.4/10

World Gone Wrong (1993) – Continuing in the vein of his last album, Dylan put out another record of traditional folk tunes with just himself and a guitar. There are a some real gems in here and the songs take on a little more serious of a tone. I just wish he had included some orginals this time around. Still a solid record. Essentials: Two Soldiers, Jack-A-Roe, Love Henry, Lone Pilgram 7.1/10

MTV Unplugged (1995) – This is a very solid, refreshing performance for Dylan. He focuses more of the attention his classics from the 60s. The arrangements are very well done and include organ, mandolin, pedal steel, and acoustic guitar. The sound is very reminiscent of the alt-country sound that Wilco was first known for at the time. A very enjoyable listen. Essentials: Shooting Star, The Times They Are A-Changin’, Dignity, With God On Our Side 8.5/10

Time Out of Mind (1997) – From the opening notes, it’s apparent Dylan is going for something a little more ambitious this time around. This album has a unique vibe that is gritty and deep with the feel and themes but also nostalgic as he brings to life some of the roadhouse blues tendencies he has dabbled with in the past. My only concern is that, at 75 minutes, the record tends to drag on a little. He could have done with a little editing with the length to make his songs more concise and punchy. But all and all, it’s great to hear Dylan’s sound brought to life again. Essentials: Love Sick, Not Dark Yet, Make You Feel My Love, Can’t Wait 7.8/10

The 2000s to Present

From the 2000s to present, Dylan put out a string of high quality (and mostly self-produced) albums, showing he still had depth as a songwriter and could create a fresh, interesting blend of styles as a producer/arranger. It’s great to see someone at his age and long years of experience (50 years since his debut!) continuing to perfect his craft and create meaningful music.

Love and Theft (2001) – Building on the momentum of Time Out of Mind, Love and Theft continues to explores past genres like rockabilly, folk, jazz and blues but in ways that sound fresh and current. There is warmth and a sense of humor this time that give the record an upbeat and relaxing vibe. With his raspy voice and the maturity of his latter day sound, Dylan sounds somewhere between Tom Waits and Randy Newman, which fits where is at as an artist. A very enjoyable listen and one of his best albums in years.Essentials: Mississippi, Summer Days, Moonlight, Po’ Boy. 8.9/10

Modern Times (2006) – Dylan’s sound has now approached a maturity, going along with his age. The songs are nostalgic, recalling old timey jazz standards and Johnny Cash style country. It’s a very well done record and a pleasant listen. However, it is missing some of the edginess of his earlier work but can one really expect that out of Dylan at this point. Although the overall length of the album isn’t as long as Time Out of Mind, every song is at least past the 5 minute mark (expect one, which is just barely under). It would have helped to flow a bit to shorten things up. Still, it’s a great listening experience.Essentials: Rollin and Tumblin, Beyond the Horizon, Thunder Mountain. 8.2/10

Together Through Life (2009) – This time around, Dylan adds a little more variety into his latter-day formula. The trademark sound of this record is the accordion, which gives the album an outdoor party feel. He also includes upright bass, banjo, mandolin and some other instruments (in addition to the usual blues guitars) to round out the sound. His voice is sounding grittier with age, which puts him further in the direction of Tom Waits. He sounds like he’s got a little bit of his edge back. In addition to mixing up the styles, he also varies the song lengths; some as short 3 minutes, others past the 5 minute mark, which overcomes the biggest flaw in Modern Times and makes for a great listen, putting this album among his best works. Essentials: Beyond Here Lies Nothin’, Forgetful Heart, I Feel A Change Comin’ On. 9.1/10

Christmas In The Heart (2009) – Dylan took this opportunity to go deeper into the nostalgic and create his first Christmas album which, as it’s cover artwork suggests, sounds like it’s from the 1950s. The results are mixed. On the one hand, his raspy voice is comparable to Louis Armstrong and gives a certain authenticity to the approach. The twangy guitars and background singers sound great. Other songs just can’t seem to pull it off and come across as campy. There are some real gems in here but it’s hard to imagine your average household throwing this one on around Christmas time. It’s seems like something more for Dylan fans or fans of the vintage. Still, you have to admire the concept and ambition. Essentials: Hark The Herald Angels Sing, I’ll Be Home For Christmas, It Must Be Santa, The Christmas Song. 6.7/10

Tempest (2012) – It’s been 50 years since Dylan released his debut. Unfortunately, Dylan lost some of the artistic moment he built in the last decade and put out a mediocre album. The main flaw is that the songs are too long. It would be forgivable but he doesn’t have as nearly as interesting arrangements as on Together Through Life. He sounds raspy and tired. Lyrically, he returns to gospel themes, songs about murder and the 13-minute long title track talks about the sinking of the Titantic. The words are alright but don’t compare to best parts of on other albums. There are some good moments on this record but all and all a disappoint compared to his later day string of high quality albums.Essentials: Pay In Blood, Scarlet Town, Tin Angel. 6.3/10

125 song Spotify Playlist: Bob Dylan Essentials Mix 

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