Perhaps no other songwriter has had the level of career that legendary lyricist and musician Bob Dylan did.

Conventionally known as possibly the best at his craft in the history of the art form – at least in modern times – Dylan has inspired many.

And on top of all his hard work, today (May 24) marks Dylan’s 81st birthday. What a feat for the longtime musical hero.

Below, we’ll take a look at the 10 songs that define Dylan’s career as a music composer and singer of poetic and narrative word strings.

So, without further ado, here are the 10 songs that define his career – no small task for the man who has released twenty studio albums and countless bootlegs, but we’ll do our best!

1. “Song to Woody”

Essentially, this song was the only original track from Dylan’s 1962 self-titled debut album. You can still see some of the baby fat on his face in the photo used for the album cover. The song was a tribute to Dylan’s hero, Woody Guthrie (more on him below). And while Dylan’s debut featured a number of traditional songs and covers, this original helped put him on the map for more.

2. “Final Thoughts on Woody Guthrie”

Less a song and more a longer spoken-word poem, this work lives in infamy for its stellar wordplay, songwriting, and reverence for American folk songwriter Woody Guthrie (known for many songs, including his standard, “This Land Is Your Land”). Dylan soars in this writing and it shows why he’s so famous, so beloved, and so standard for other writers in his wake.

3. “Blow in the wind”

After Dylan’s debut album helped put him somewhat on the map — at least on the New York folk scene of the 1960s — this song helped solidify him as a future legend from 1963 onwards. How many roads does a man have to travel before you call him a man? Is there a more famous saying by Dylan? If there is one, there was none more useful for his early career.

4. “The Times They Change”

The next song to cement Dylan as someone to be reckoned with in the music scene, this track showed what a timeless performer he was. This song came out in 1964 and got a lot more notice. And look, Dylan lost all of his Minnesota baby fat from his face. He is now a hardened adult and is starting to become one of America’s most famous entertainers. This made him one of the world’s most famous acoustic “protest singers” in the tumultuous 1960s.

5. “It’s Not Me Baby” with Joan Baez

Another of Dylan’s greatest songs, this one makes the list not just for its stellar songwriting and catchy chorus, but for its association with the queen of folk music at the time, Joan Baez, with whom Dylan sings the breakup song onstage in 1964. It’s ironic, soon he and Baez would go their separate ways after their famous relationship. It’s cute to see them singing together here. Dylan’s romance with Baez further helped make him famous.

6. “It’s alright, mom (I’m just bleeding)”

Is this the very first rap song? Dylan plays as much rhythm on his guitar as he does a traditional song. On the floor, Dylan spits fire, as the kids would say now. It’s a robust track that might just be the first rap song of all time. For that alone, he makes the list. It was released on the 1965 album, bring it all home.

7. “Lay down, lady, lay down”

As Dylan (famous) broke away from the acoustic songwriting he had become known for, he tried many different sounds and genres. Here, many fans claim he was doing his best Johnny Cash impression, singing full-throated and softer than he had done so far. The song was a hit, one of the few in the middle of Dylan’s career as an artist.

8. “Isis”

One of the greatest breakup songs of all time, this song marks another hit for the writer in his final stages. The narrator of the melody is heartbroken, so he goes on a quest. Someone asks for his help. Whether the quest was worthwhile or not wasn’t the issue. Entertainment was, in fact, the goal. Anyone who’s had their heart broken knows that too. Dylan captures it impressively here and got some of us (ahem) to listen to it again and again when needed.

9. “Sick Love”

Dylan’s career took a turn in the 1980s and his star fell a little in the eyes of popular music fans. However, Dylan is unlikely to care about that. However, the artist made a small comeback with his album time out of mind, which dropped in 1997. With it, this song went wild around the world and was Dylan’s biggest hit in years. The dark, sometimes morbid singing, carried by an organ, is formidable, that’s for sure.

10. “Frudest Murder”

The first single from Dylan’s latest studio release, Rough and rowdy ways (2020), we had to include this song in the list here. And it lasts more than 16 minutes. It’s a long track to follow, more novel than hit single. But it also marks Dylan’s most recent milestone as a songwriter and artist, so it’s worth digging in and analyzing from here until his next release, whatever the date.

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