Top 5 Bob Dylan Songs By Decade

One of my favorite bloggers – professor, media critic and television star Dan Kennedy – has thrown down the gauntlet with his list of the Top 5 Bob Dylan songs. Naturally, this is an impossible task. My initial short list – where I tried to cull Dylan’s immense catalog down to the best of the best from each official (quality) release – hovered at 32 songs. Like Dan says, a Dylan fan can make a new top 5 list every day, but just for fun I’ll organize mine by decade.

But first, a quick story: About 5 years ago my parents were visiting. My dad was perusing the CD library. Spotting the shelf o’ Dylan he innocently asked: “Who this Bob Die-lon?” My Mom, who hasn’t followed music since American Bandstand in the 50s, snapped back: “You idiot! That’s Bob Dylan. Even I know that!” It was a priceless family moment. Obviously my parents weren’t frequenting coffeehouses in the Village back in the day.

Top 5 Dylan Songs by Decade


The 1960s represent Dylan’s most prolific and successful era. He released 9 albums – all of them good to great – spanning acoustic folk, electric rock and country and became the unwilling spokesman for his generation along the way.

“Bob Dylan’s Dream” from The Freewheelin’ Bob Dylan

Representing folkie Bob, I love this early acoustic number. The melody is nothing special but the vocal delivery is skilled and highly emotional. It paints a very human picture and listening to it I can picture a young Dylan leaving Minnesota to take his chances in NYC. Wistful of the past, while reluctantly embracing the impermanence of life, there’s nothing here to protest.


The 70s started and ended rough for Bob with several bad albums released as a result of record company politics and his dreaded (dreadful?) born-again phase. But in the middle of the decade he put together a legendary three album run: Blood on the Tracks-The Basement Tapes-Desire.

“You’re a Big Girl Now” from Blood on the Tracks

I never get tired of hearing this one. The melody is great. The guitar work is subtle. His vocals are full of pain and the phrasing is excellent. Even his harp is crying at the end. It’s a great song from an exceptional album. This time Dylan is angry, defeated and mourning the end of a relationship.


Dylan is unfairly maligned for his 80s output. Yes, the decade kicked off with more gospel crap. And his “return to rock” albums are marred by the cheesy productions that ruin all great 80s rock. But from a songwriting perspective, there are some gems: Infidels, Empire Burlesque and Oh Mercy are all solid albums.

“Shooting Star” from Oh Mercy

It’s hard to listen to Oh Mercy these days without thinking about Bob’s book Chronicles, Vol. 1 (aka “How I Got My Mojo Back”). Oh Mercy is certainly not one of Dylan’s best albums, but he must view it as the project that gave him his voice back. Shooting Star is a delicate tune (again mourning a failed relationship) that foreshadows the craftsmanship evident in the later-period Dylan albums. Or maybe that’s just the Lanois-effect?


There’s not much to choose from in the 90s. Bob only released 4 albums. One was junk and two were folk-cover albums. Thank God for “Time Out of Mind” which, hype aside, is truly an excellent piece of work.

“Standing in the Doorway” from Time out of Mind

The tone and atmosphere of this album is perfect. This is an entirely new Dylan. His voice is ragged and yet he inhabits it better than perhaps any other singing voice employed in his career. It’s sparse and dense at the same time. The song (I’m sensing a theme here) is about Dylan thinking back to one of those failed relationships, his heart never fully recovered.


We’ve gotten two albums out of Bob this decade and we probably won’t be seeing any more. That’s okay, because they’re both quite good – even if Bob seems to have pinched much of the music and lyrics for Modern Times.

“Po’ Boy” from “Love & Theft”

“Po’ Boy” is a slight tune off of “Love & Theft” that I absolutely adore. It’s either the story of a hobo or the story of a man who’s rootless in love – an emotional hobo. Either way, it’s got a heaping serving of that whimsical troubadour Dylan that was so evident on his early albums.

Okay, I can’t possibly be saying (but I guess I am) that the Top 5 Dylan Songs by decade are:

“Bob Dylan’s Dream” from The Freewheelin’ Bob Dylan
“You’re a Big Girl Now” from Blood on the Tracks
“Shooting Star” from Oh Mercy
“Standing in the Doorway” from Time out of Mind
“Po’ Boy” from “Love & Theft”

Here’s the rest of the short list, in case you were wondering:

The Freewheelin’ Bob Dylan (1963): “Girl from the North Country”, “Bob Dylan’s Dream”, “Corrina, Corrina”

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

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

Highway 61 Revisited (1965): “It Takes a Lot to Laugh, It Takes a Train to Cry”, “Ballad of a Thin Man”, “Just Like Tom Thumb’s Blues”

Blonde on Blonde (1966): “Visions of Johanna”, “4th Time Around”

John Wesley Harding (1967): “I’ll Be Your Baby Tonight”

Nashville Skyline (1969): “I Threw it All Away”, “Tonight I’ll Be Staying With You”

Planet Waves (1974): “Forever Young”

Blood on the Tracks (1975): “Simple Twist of Fate”, “You’re a Big Girl Now”

Desire (1976): “Oh, Sister”, “Sara”

Street Legal (1978): “Senor”

Empire Burlesque (1985): “I’ll Remember You”, “Dark Eyes”

Down in the Groove (1988): “Silvio”

Oh Mercy (1989): “Disease of Conceit”, “Shooting Star”

Time Out of Mind (1997): “Standing in the Doorway”, “Not Dark Yet”, “Make You Feel My Love”

Love & Theft (2001): “Mississippi”, “Po’ Boy”

Modern Times (2006): “Spirit on the Water”, “Workingman’s Blues #2”, “Nettie Moore”


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