I was at my local Hoboken, NJ bar the other night and someone asked me if I were ever to be stranded on a desert island and could only bring 5 Bob Dylan albums, which ones would I bring?

I couldn’t answer him right away, and not because I had already had a good buzz after drinking four bottles of Miller Lite (note: I’m a lightweight), I had to think about that for a while because I love Bob Dylan. Wait, let me rephrase that, I REALLY LOVE BOB DYLAN!

For anyone even remotely aware of American pop culture over the past 40 years, it would be tough to miss the direct impact and lasting influence of Dylan’s songs. I needed time to get back in touch with ALL things B-O-B!

After spending a WHOLE week revisiting all my Dylan CDs I compiled these 5 as the very ones I’d like to have with me if I were stranded on a desert island. And with this list I hope I can introduce the genius of Dylan to people walking around now who’ve never heard of the guy, or have no awareness of him beyond simple name recognition.

So if I, Adam Wade, was stranded on a desert island and could only have 5 Bob Dylan albums, which ones would I bring? Here’s my list:


05) The Freewheelin’ Bob Dylan

Dylan’s second studio album, released in 1963 by Columbia Records.

This is first Bob Dylan CD I bought (besides the Greatest Hits 1, 2 and 3 – which my parents already owned). I feel like a tool saying this but when I bought this CD at the mall when I was in high school, and I did it simply because I liked the photo on the cover. It was of Dylan with his then-girlfriend Suze Rotolo. The photo was taken at the corner of Jones Street and West 4th Street in Greenwich Village, New York City – just a few yards away from the apartment where they lived at the time.

In Cameron Crowe’s film Vanilla Sky, the main character, David (played by Tom Cruise), walks with Sofia (Penélope Cruz)  recreating this classic album cover.  I’m from the mean streets of rural New Hampshire, so this album cover had me dreaming of New York City and the Folk Music Revival of the 1960s. The songs on this album blend both the innocence of a young man and the knowledge of an elderly educated man who’d seen it all. Incredible stuff!

  1. “Blowin’ in the Wind” – 2:48
  2. “Girl from the North Country” – 3:22
  3. “Masters of War” – 4:34
  4. “Down the Highway” – 3:27
  5. “Bob Dylan’s Blues” – 2:23
  6. “A Hard Rain’s a-Gonna Fall” – 6:55
  7. “Don’t Think Twice, It’s All Right” – 3:40
  8. “Bob Dylan’s Dream” – 5:03
  9. “Oxford Town” – 1:50
  10. “Talkin’ World War III Blues” – 6:28
  11. “Corrina, Corrina” (Traditional) – 2:44
  12. “Honey, Just Allow Me One More Chance” (Dylan, Henry Thomas) – 2:01
  13. “I Shall Be Free” – 4:49

Moods to listen to this album: reflective, mellow, jovial.

Key songs of the album: (three of the greatest protest songs of the 60s)

  • A Hard Rain’s a-Gonna Fall
  • Masters of War
  • Blowin’ in the Wind

Dark Horse songs of the album:

  • Don’t think Twice (great breakup song)
  • Talkin’ World War III Blues (one of the funniest Dylan songs)

NERD NOTE: A dark horse candidate is one who is nominated unexpectedly, without previously having been discussed or considered as a likely choice. Often a dark horse is selected as a compromise when other, more prominent candidates’ factions cannot come to an agreement. This metaphoric expression originally alluded to an unknown horse winning a race and was so used in a novel by Benjamin Disraeli (The Young Duke, 1831).

04) Bringing It All Back Home

Bringing It All Back Home is Bob Dylan’s fifth studio album, and was released in 1965 by Columbia Records.

The album, Bringing It All Back Home, is divided into 2 sides – an electric and an acoustic. On side one of the original LP, Dylan is backed up by an electric rock’n’roll band – a move that further separated him from some of his former peers in the folk community. Also, on the acoustic side of the album, he dissociated himself from the protest songs with which he had become closely identified with, as his lyrics continued drifting toward the abstract and personal. Bringing It All Back Home is often cited by rock historians as the birth of the folk-rock movement, and one of the pinnacle of Dylan’s career. The album reached #6 on Billboard’s Pop Albums chart, the first of Dylan’s LPs to break into the US top 10.

  1. “Subterranean Homesick Blues” – 2:21
  2. “She Belongs to Me” – 2:47
  3. “Maggie’s Farm” – 3:54
  4. “Love Minus Zero/No Limit” – 2:51
  5. “Outlaw Blues” – 3:05
  6. “On the Road Again” – 2:35
  7. “Bob Dylan’s 115th Dream” – 6:30
  8. “Mr. Tambourine Man” – 5:30
  9. “Gates of Eden” – 5:40
  10. “It’s Alright, Ma (I’m Only Bleeding)” – 7:29
  11. “It’s All Over Now, Baby Blue” – 4:12

Moods to listen to this album: mellow, groovy, trippy, slightly rocking

Key songs of the album:

  • It’s All Over Now
  • Baby Blue (incredible lyrics)
  • It’s Alright, Ma
  • I’m Only Bleeding (another terrific protest song)

Dark Horse songs of the album:

  • Bob Dylan’s 115th Dream (funny, funny show)
  • Love Minus Zero/No Limit (great folk-rock song to play right when you fall in love)

03) Blonde on Blonde

Blonde on Blonde is Dylan’s 7th studio album, released in 1966 by Columbia Records..

This was believed to be the first double album in modern rock.  Widely regarded as one of Dylan’s greatest albums.  Blonde on Blonde marked the end of the electric/rocking period for Dylan, who would soon be involved in an almost deadly motorcycle accident, and disappeared from the scene to recuperate in rural Woodstock, NY.  When he’d return some time later, he considerably changed his musical approach.

  1. “Rainy Day Women #12 & 35” – 4:3
  2. “Pledging My Time” – 3:50
  3. “Visions of Johanna” – 7:33
  4. “One of Us Must Know (Sooner or Later)” – 4:54
  5. “I Want You” – 3:07
  6. “Stuck Inside of Mobile with the Memphis Blues Again” – 7:05
  7. “Leopard-Skin Pill-Box Hat” – 3:58
  8. “Just Like a Woman” – 4:53
  9. “Most Likely You Go Your Way (And I’ll Go Mine)” – 3:30
  10. “Temporary Like Achilles” – 5:02
  11. “Absolutely Sweet Marie” – 4:57
  12. “4th Time Around” – 4:35
  13. “Obviously 5 Believers” – 3:35
  14. “Sad Eyed Lady of the Lowlands” – 11:23

Moods to listen to this album: mellow, pre-party mood, post-party mood

Key songs of the album:

  • Visions of Johanna (Dylan’s finest rocking love song)
  • Just Like a Woman (mellow love song, feels like Dylan and a few bandmates are playing right in your living room)

Dark Horse songs of the album:

  • Sad Eyed Lady of the Lowlands (the most personal love song he’d done up to that time, for his wife Sara)
  • Leopard-Skin Pill-Box Hat (fun, fun, fun)

02) Blood on the Tracks

Blood on the Tracks is Dylan’s 15th studio album, released in 1975 by Columbia Records, which marked Dylan’s return to Columbia after a two-album detour with Asylum Records.

After a couple of years of lukewarm reviews for Dylan’s work, Blood on the Tracks was greeted favorably by both critics and fans. Throughout the years it is now seen as one of his finest albums. Most of the lyrics deal with heartache, anger, and loneliness.

  1. “Tangled Up in Blue” – 5:42
  2. “Simple Twist of Fate” – 4:19
  3. “You’re a Big Girl Now” – 4:36
  4. “Idiot Wind” – 7:48
  5. “You’re Gonna Make Me Lonesome When You Go” – 2:55
  6. “Meet Me in the Morning” – 4:22
  7. “Lily, Rosemary and the Jack of Hearts” – 8:51
  8. “If You See Her, Say Hello” – 4:49
  9. “Shelter from the Storm” – 5:02
  10. “Buckets of Rain” – 3:22

Moods to listen to this album: sad (great post breakup album), restless

Key songs of the album:

  • Tangled Up In Blue (one of his best songs, peaked at #31 on the Pop singles chart)
  • Shelter from the Storm

Dark Horse song of the album:

  • Lily, Rosemary and the Jack of Hearts – the fastest song on the album.  A fun bar room song, the most optimistic song of the bunch.

01) Slow Train Coming

Slow Train Coming was Dylan’s 19th studio album, released in 1979 by Columbia Records.

Even though it was his first album since becoming a born-again Christian, you need not be a Jesus-freak to enjoy it and appreciate what he’s trying to do. His passion for the lyrics and the music is off the charts.  Once again, he’s done the unexpected. The reviews for it were above average and the single “Gotta Serve Somebody” became his first hit in three years.  But to me the two songs that stick out are ‘Precious Angel’ and ‘I Believe in You,’ mainly because of the accompaniment of Dire Staits Mark Knopfler’s guitar.  It’s a perfect fit and you can get his gentle riffs out of you mind.  They are two songs you wish would never end. So yes, if you only listen to one Christian Rock record, do yourself and favor and listen to this one.

  1. “Gotta Serve Somebody” – 5:22
  2. “Precious Angel” – 6:27
  3. “I Believe In You” – 5:02
  4. “Slow Train” – 5:55
  5. “Gonna Change My Way Of Thinking” – 5:25
  6. “Do Right To Me Baby (Do Unto Others)” – 3:50
  7. “When You Gonna Wake Up” – 5:25
  8. “Man Gave Names To All The Animals” – 4:23
  9. “When He Returns” – 4:30

Moods to listen to this album: reflective, soul searching

Key songs of the album:

  • Precious Angel
  • Slow Train,
  • Gotta Serve Somebody

Dark Horse song of the album:

  • When He Returns (just the organ and Dylan’s voice)

NERD NOTE: October 18, 1979, was the night of Dylan’s first and only appearance on the American TV show Saturday Night Live. The songs he performed on the show were “Gotta Serve Somebody,” “I Believe In You,” and “When You Gonna Wake Up.”

So these are the 5 Bob Dylan albums I’d personally want with me if I were ever to be stranded on a desert island. I hope I was able to give you a glimpse of the greatness that is Dylan.

One last important note: All these albums differ from one another giving you, the listener an opportunity to see some of the MANY sides of the former Robert Zimmerman, the pride of Hibbing, Minnesota. I hope you’ll take the time to check them all out. Happy listening.