1.) Bob Dylan (1962). Dylan's debut album consists mostly of cover songs of artists like Bukka White, Dave Van Ronk, and Blind Lemon Jefferson. The two original songs are "Talkin New York" and "Song to Woody," written to one of Dylan's major early influences, Woody Guthrie.
2.) The Freewheelin' Bob Dylan (1963). This album, composed mainly of original songs, became a much bigger hit than his debut, and propelled Dylan to the forefront of 1960s youth culture. It has many iconic 60s Dylan songs like "Blowin' in the Wind," "Masters of War," and "A Hard Rain's a-Gonna Fall." Mixed in with these political/social songs are some very beautiful love songs like "Girl from the North Country." This may be my favorite Dylan album.
3.) The Times They Are 'A Changin' (1964). The title track became a sort of anthem of 1960s social protest and change. Continuing the themes of political and social consciousness, this album deals with issues of racism ("The Lonesome Death of Hattie Carroll"), American Imperialism ("With God on Our Side"), and overall social change ("When the Ship Comes In"). The song "Boots of Spanish Leather" is one of the most heartbreaking and beautiful relationship songs ever, in my opinion.
4.) Another Side of Bob Dylan (1964). This album marked a departure from the socially-conscious music of his previous albums, and focused on more personal themes in songs like "It Ain't Me Babe" and "All I Really Want to Do." The Byrds covered four songs from this album, including "Chimes of Freedom."
5.) Bringing it all Back Home (1965). This album marked Dylan's entrance into "rock music" with a full electric band. Notable songs are "Subterranean Homesick Blues" and "Maggie's Farm." The second side of this album contains more traditional folk songs, including "Mr. Tamborine Man."
6.) Highway 61 Revisited (1965). This album moved Dylan further into "electric music." Every song features a full backing band, with the exception of the closing track "Desolation Row." Probably the most famous song off this album is "Like a Rolling Stone." This album is named after the US highway that connects Dylan's hometown of Duluth, Minnesota to southern cities known for their music heritage, like Memphis, St. Louis, New Orleans, and the Mississippi Delta. Two "blues" songs are "Tombstone Blues" and "Just Like Tom Thumb's Blues."
7.) Blonde on Blonde (1966). This is an epic double-album which contains one of my favorite Dylan songs, "Visions of Johanna." Dylan recorded this album with the band that would become The Band, with important musicians Robbie Robertson and Levon Helm. Dylan and The Band would continue to collaborate well into the 1970s. Other notable tracks off Blonde on Blonde are "One of Us Must Know (Sooner or Later)," "Stuck Inside of Mobile With the Memphis Blues Again," and "Just Like a Woman." Pretty much every song on this record is a gem.
8.) John Wesley Harding (1967). Between the release of Blonde on Blonde and this album, Dylan had a motorcycle accident which caused him to stop touring for nearly 8 years. Instead, he focused on writing and recording. John Wesley Harding was recorded in Nashville, and contains the hit song "All Along the Watchtower," which was famously covered by Jimi Hendrix.
9.) Nashville Skyline (1969). Throughout his long and storied career, Bob Dylan has often re-invented his sound. This is definitely true of Nashville Skyline, which is pretty much a straight-ahead country album, and features a new, more melodic style of singing. This album features a great duet with Johnny Cash ("Girl from the North Country"). Nashville Skyline also contains the hit single "Lay Lady Lay."
10.) Self Portrait (1970). This album was harshly criticized by critics. It contains a lot of cover songs, and is generally regarded as his weakest album thus far. There are some goods tracks on it, however, like "Copper Kettle," and "The Mighty Quinn (Quinn the Eskimo)." The song "Wigwam" is featured in Wes Anderson's film The Royal Tennenbaums.
12.) Pat Garrett and Billy The Kid (1973). This was a soundtrack album for director Sam Peckinpah's film Pat Garrett and Billy the Kid, starring James Coburn, Kris Kristofferson, and Bob Dylan himself! The most famous song off this album is "Knockin' On Heaven's Door."
13.) Dylan (1973). This album was compiled of cover songs, outtakes from Self Portrait and New Morning, with no input from Dylan himself. Columbia put this record out after Dylan announced that he was leaving the label for Asylum Records. Though it was not well-received critically, I like the first three tracks: "Lily of the West," "Can't Help Falling in Love," and "Sarah Jane."
14.) Planet Waves (1974). This album was a collaboration with The Band, it was was well-received. It contains the song "Forever Young." My favorite tracks are "On a Night Like This" and "Tough Mama."
16.) The Basement Tapes (1975). This is a series of recordings made by Bob Dylan and The Band in 1967, when they were all living in Woodstock, NY, when Dylan was convalescing and recovering after his motorcycle accident. The album has a rootsy, Americana feel. My favorite songs off the Basement Tapes are "Bessie Smith," "You Ain't Goin' Nowhere," and "Tears of Rage."
18.) Street Legal (1978). This album was not well-received in the US, but it fared better in the UK. My favorite track is "Changing of the Guards."
19.) Slow Train Coming (1979). In 1979, Bob Dylan became a "born again" Christian, and this conversion prompted him to make three albums that were heavily influenced by his Christian faith. This alienated many of his fans, but also gained him a following among some Christians. Despite their somewhat negative reputation, I think there are some real musical gems on these next three albums. My favorite songs on Slow Train Coming are "Gotta Serve Somebody," "Man Gave Names to All the Animals," and "When He Returns."
20.) Saved (1980). As you can tell by the title and cover of this album, it is the most overtly Christian of Dylan's records, and represents the most intense music of his "born again" phase. The 1970s were a strange decade in America. The "Jesus Movement" was a big deal, with lots of hippies converting to "born-again" Christianity, and I think Dylan's records reflect this strange cultural moment in the US. I don't love this album, but it has a couple decent tracks: "A Satisfied Mind" and "Saved," the title track.
21.) Shot of Love (1981). The third album on his unofficial "Christian trilogy, Shot of Love shows signs of Dylan leaving his days of sermonizing and returning to "secular" topics, as shown in the song "Lenny Bruce," a sort of musical eulogy to the radical comedian. This most overtly Christian song on this album is "Property of Jesus," which is actually a pretty moving song. I think my favorite song on this record is "Heart of Mine."
22.) Infidels (1983). It's appropriate that the album that broke Dylan's "Christian series" is called "Infidels." My friend Paul, who has been a Dylan fan since probably the 60s, once made the observation that, even after Dylan's gospel albums, there remains a lingering interest in religion and spirituality in his music, and I totally agree. Musically speaking, the religious albums gave Dylan another stylistic influence to work with--gospel--a super important and rich American musical tradition. The opening track on Infidels, "Jokerman," has biblical overtones, but could also be about America. Also, on Infidels, we find Dylan returning to "protest/topical music" with the song "Union Sundown," which is about the decline of manufacturing unions due to an increasingly globalized economy, which was certainly happening in 1983, when Infidels was recorded.
23.) Empire Burlesque (1985). This is generally regarded as one of Dylan's worst albums, and I tend to agree. The 1980s were a difficult decade for Bob Dylan (and a lot of musicians who came of age in the 1960s--like Paul McCartney, Brian Wilson, and The Kinks). It was the decade of transition from analog to digital/electronic recording, and slick studio sound just doesn't suit Bob Dylan. Having said that, I do think "Clean Cut Kid" is a good song, both musically and content-wise--it's about a Vietnam Veteran having trouble adjusting to civilian life.
24.) Knocked Out Loaded (1986). While this album still suffers from some 1980s-itis, the hi-light is definitely the eleven-minute epic "Brownsville Girl," which hearkens back to the highly poetic/complex 60s Dylan tracks like "Visions of Johanna." Another good track is "They Killed Him," which is about the deaths of important human rights leaders like Gandhi and MLK.
25.) Down in the Groove (1988). My favorite track on this album is actually a cover of a traditional folk song called "Shenandoah." I also like "Death is Not the End," which has a gospel feel to it. Throughout the 1980s, Bob Dylan made extensive use of black female backing singers, which give the songs a definite gospel/blues feel.
26.) Oh Mercy (1989). After what many critics considered to be a creative slump, Dylan made yet another "comeback" album with Oh Mercy. This album contains the hit single "Most of the Time," a very honest confessional-type song. This introspective feel is also present on "What Good Am I?" There's also a pretty gospel-y song called "Ring Them Bells," which was covered by the great indie singer-songwriter Sufjan Stevens for the soundtrack of the Bob Dylan bio-pic "I'm Not There."
28.) Good as I Been to You (1992). This album marked yet another transition in Dylan's career. He got rid of his band and recorded an entire album of songs that include only acoustic guitar and Dylan's voice. It's as if he was shedding his skin, cleansing himself of all the bullshit of the 1980s, getting back in touch with the folk, blues, and ballads that first inspired him so many years ago. But this album isn't about nostalgia--Dylan's voice now bears the scars and authority of experience. He has become one of the "old masters" that he so admired in his youth in Greenwich village in New York of the 1960s. This is a great album, especially in light of what came before it. My favorite song on this album is a cover of Mississippi John Hurt's "Frankie and Albert."
29.) World Gone Wrong (1993). This is another album of guitar and voice tracks of traditional folk songs. World Gone Wrong actually won the Grammy for Best Traditional Folk Album. My favorite song on this one is Dylan's cover of Blind Willie McTell's song "Broke Down Engine." I feel like, on these two acoustic albums, Dylan discovered that his aging voice and style was well-suited to old school blues music, a style that would dominate the next phase of his career.
30.) Time Out of Mind (1997). This record won three Grammys, including Album of the Year, marking yet another creative re-invention for Dylan. After the previous folk records, this album marks the return of Dylan with a full band. However, with this record, Dylan shed the slick 1980s sound, and returned to a more authentic roots/blues/folk sound. This album is really good. The two singles off it were "Not Dark Yet" and "Love Sick." "Tryin' to Get to Heaven" is another great track.
31.) Love and Theft (2001). This album was released on September 11th, 2001. Music critic Greg Kot describes the album in this way: "This is a tour of American music--jump blues, slow blues, rockabilly, Tin Pan Alley ballads, Country swing--that evokes the sprawl, fatalism and subversive humor of Dylan's sacred text, Harry Smith's Anthology of American Folk Music, the pre-rock voicings of Hank Williams, Charley Patton and Johnnie Ray, among others, and the ultra dry humor of Groucho Marx." Without a doubt, the best song on "Love and Theft" is "Mississippi," one of Dylan's best songs ever.
32.) Modern Times (2006). Upon the heels of his success with Time Out of Mind and "Love and Theft," Dylan made yet another critically and commercially successful record with "Modern Times." These recent Dylan albums show a master at work who is well steeped in American music, has encyclopedic knowledge of singers, songwriters, and poets, and manages to mix all these elements together into an album that feels really deep and expansive. Here are some of the diverse musical and literary references in Modern Times: Henry Timrod (19th century poet), Memphis Minnie (blues singer), Chuck Berry (rock and roll pioneer), Hambone Willie Newbern (country blues singer), Lightnin' Hopkins (Texas bluesman), Sleepy John Estes (blues legend), Muddy Waters (Chicago bluesman), June Christy (cool jazz singer), Willie Dixon (blues musician), Howlin' Wolf (bluesman), Big Joe Williams (Delta blues singer), James Lord Pierpont (19th century composer), Kansas Joe McCoy (Delta bluesman), Led Zeppelin (British rockers), The Stanley Brothers (bluegrass duo), and Ovid (ancient Roman poet). The single off Modern Times was "Someday Baby."
33.) Together Through Life (2009). From 2006-2009, Bob Dylan hosted a weekly radio show called "Theme Time Radio Hour" for satellite radio. Each episode centered on a theme (Weather, Money, Flowers, etc.) and featured an eclectic mix of music that Dylan liked. With the release of Together Through Life, Dylan also included an episode of his radio show called "Friends and Neighbors." It features a collection of songs that gives great insight into the diverse musical influences of this record. Featured artists include Porter Wagoner and the Wagonmasters, Sister Rosetta Tharpe, T-Bone Burnett, Moon Mullican, George Jones, Melba Montgomery, Howlin' Wolf, Little Walter, Carole King, The Rolling Stones, Hank Williams, and War. My favorite tracks on Together Through Life are "Shake Shake Mama" and "I Feel a Change Comin' On."
This year, Bob Dylan released an album of Frank Sinatra covers called Shadows in the Night, which I haven't listened to yet, and decided not to include on this list. Anyway, the point is that Bob Dylan is a super important American musician whose catalogue is vast and deep. Listening to these albums has been both educational and inspiring for me.