The definitive Bob Dylan playlist

The opening number and title cut from Dylan's eighth studio album, released in 1967. Dylan reportedly had a thing for outlaw history, the Old West, and those characters who were part of the lore. John Wesley Hardin earned infamous acclaim during the late 19th century, and according to Down the Highway: The Life of Bob Dylan, the artist accidentally added the "g" onto the outlaw's last name. As we'll see, the album also features one of rock's biggest hits, but this track holds its own within Dylan's expansive catalog.

Initially recorded in 1967 by Dylan in collaboration with the Band. The Band put out its take of the tune a year later on Music from Big Pink. Boz Burrell also did, best known for his work with King Crimson and Bad Company. A re-recorded Dylan version was released in 1971 on Bob Dylan's Greatest Hits Vol. II. The track might best be remembered for its inclusion in the Band's The Last Waltz farewell concert, which featured Dylan, Ronnie Wood, Ringo Starr, and Joni Mitchell.

From Dylan's 1974 album Planet Waves, "Forever Young" appears twice on the record. There is one faster, tighter version and a slower, longer take. Regardless of which is preferred, "Forever Young" has been one Dylan song that's spanned generations. Its lyrics became a children's book, and the tune served as the theme of the popular television show Parenthood. 

Three decades after the release of John Wesley Harding, Dylan was still delivering the goods on 1997's Time Out of Mind. "Love Sick" is the opening track and one of Dylan's more unique recordings from a production standpoint. It almost sounds like a rough demo, with its grainy, hollow vibe that proved Dylan was willing to spice things up and think outside the box through the years. He performed the song at the 1998 Grammy Awards.

One of the special moments from Dylan's 1963 breakout second album, The Freewheelin' Bob Dylan. The album version alone was worth the price of the vinyl record back in the day, but the song earned even more acclaim six years later when he re-recorded it as a duet with fellow legend Johnny Cash. The latter version was featured on Dylan's ninth studio album, Nashville Skyline. While Dylan fans have their preferred take, one can't go wrong.

More greatness from The Freewheelin' Bob Dylan. It's prime proof that Dylan is a poet by heart. The piece began as a poem, turned into a ballad, then blossomed into one of the great acoustic tracks of the 1960s. All through the eyes of Dylan, who subtly broaches topics like war, collective suffering, and even a little self-reflection. Perhaps not the most cheery tunes of the time, but a classic nonetheless. 

We'll stick with Time Out of Mind, proving once again that age meant nothing to Dylan when releasing quality music. "Not Dark Yet" is more polished than "Love Stick" and offers a contemporary feel while not losing the signature Dylan sound that sometimes went missing over the years when he wanted to veer and try something different. Since its release, "Not Dark Yet" was regularly played during Dylan's live shows and has been covered by the likes of Tom Jones, Lucinda Williams, and Robyn Hitchcock.

Found on the John Wesley Harding album, Dylan released the original version of "All Along the Watchtower" six months before Jimi Hendrix's more well-known cover, which became a top 20 single and eventually won the guitar hero a posthumous Grammy Award in 2001. Still, there is something special, raw, and primitive about Dylan's stripped-down original about the joker and the thief. Let's not forget that stellar harmonica work.

Dylan wrote this heartbreaking, agonizing song in 1975, reportedly while breaking up with his first wife, Sara Lownds. However, it was not released until 1985, when included in the box-set compilation Biograph. To the novice ear, without knowing any of the backstories of Dylan's break-up, it's obvious this is a man in emotional pain. Of course, Dylan has always been one of if not the best at channeling his emotions into memorable musical art. 

It's a safe bet that plenty of teens and college-aged music fans during the 1990s thought Guns N' Roses wrote this song. A little more than 20 years before it became a hit cover for Axl, Slash, and Co., Dylan enjoyed success after writing the popular track for the 1973 Western film Pat Garrett and Billy the Kid. Dylan's slower, original version peaked at No. 12 on Billboard's Hot 100. By comparison, the amped-up G N' R version stalled at 18 on Billboard's Mainstream Rock chart.

The first of several tracks from Dylan's mega-classic Blonde on Blonde double album from 1966. "I Want You" kicked off Side Two of the vinyl offering and has been played at a few different speeds during Dylan's live sets. Though, the peppy, spirited studio version still seems to stand out above the rest. A rather prompt song (barely over three minutes), "I Want You" is just one of many Dylan songs that inspired Bruce Springsteen, who no doubt tried to emulate Dylan in his early days. The Boss's cover of this tune is worth a listen.

When Bob Dylan channels his anger into his music, the result is pretty powerful. On 1965's Bringing It All Back Home, "It's Alright, Ma (I'm Only Bleeding)" is Dylan channeling his disdain for socio-political issues like commercialism and consumerism. Delivered in almost spoken-word form, the track has stood the test of time well, notably for lyrics such as, "He not busy being born is busy dying," which Jimmy Carter included in his presidential nomination speech at the 1976 Democratic National Convention.

Another Blonde on Blonde gem and another song that was a bigger hit for an artist not named Dylan. Manfred Mann had a top-10 hit with its version of "Just Like a Woman" in the United Kingdom. Meanwhile, Dylan's original reached No. 33 on Billboard's Hot 100 in the United States. Either way, the track is one of Dylan's most talked about. Notably, this deeply personal tune has long been criticized as being sexist and misogynistic toward an ex-love of Dylan's.  

One of Dylan's most personal songs. A tune of redemption is almost haunting and gospel-like. From 1981's Shot of Love, "Every Grain of Sand," to the casual fan of the legend, is an underrated Dylan song that tends to be lost in the massive shuffle of his other iconic works. That said, it's not forgotten. Emmylou Harris performed the tune at the celebration of Dylan's 75th birthday in 2016.

The rollicking "Subterranean Homesick Blues" was Dylan's first top-40 hit single in the United States. The lead track from Bringing It All Back Home reached No. 39 on Billboard's Hot 100 and was a top-10 hit in the United Kingdom. Plenty of Dylan's musical influences (folk, blues, rock) are all incorporated into one of his best-known tracks, which is also notable for the associated video (or promotional film clip) of him standing outside, flipping cards with selected lyrics from the song. INXS indirectly paid homage to the clip initially used in the Dylan tour documentary Don't Look Back for its "Mediate" video from the 1987 Kick album.

It's interesting to note that one of folk rock's most popular and recognizable songs was never released as a single in the United States. However, it was a top-10 hit in the U.K. From the 1964 album by the same name, it's been reported that Dylan was trying to write an anthem for the time with the hope of inspiring change. His lyrics inspired Dylan's young folk and rock fans and some of the most important musical artists of all time, such as Nina Simone, Bruce Springsteen, and Billy Joel.

Plenty of classic rock fans, or novice Dylan fans, tend to believe this Blonde on Blonde opener is titled "Everybody Must Get Stoned." Of course, that's not the case, but the line in this whimsical and even controversial (for that particular phrase) track is among Dylan's most recognizable. The song has enjoyed legendary status amid Dylan's massive musical arsenal and even peaked at No. 2 on Billboard's Hot 100. 

One of the most recognizable and celebrated folk songs of all time. It can be found in its original form on Dylan's Bringing It All Back Home. However, the tune is likely best known for a much shorter, poppier version by The Byrds, which went to No. 1 on Billboard's Hot 100 and the U.K. Singles chart. Regardless of which version is to one's liking, "Mr. Tambourine" falls under the "iconic" category where plenty of Dylan's work resides.

While known for his emotional ballads and innate poetic ability, Dylan is a masterful storyteller. Of course, he liked to draw from historical moments or even controversial news of the day. The latter describes "Hurricane," from Dylan's 1967 Desire LP. This protest piece chronicles the arrest and conviction of successful Black boxer Rubin "Hurricane" Carter and his friend, John Artis, who were falsely imprisoned for a 1966 triple murder in New Jersey. The song called out the police and courts for racial profiling. Dylan got involved with trying to get Carter out of prison, which eventually happened in 1985. 

'"The answer, my friend, is blowin' in the wind" is one of the most famous lines in music history — the undisputed highlight of The Freewheelin' Bob Dylan and among the greatest protest songs of all time. Dylan offers questions about freedom and peace and how both can be threatened by war. Was "Blowin' in the Wind" ahead of its time? Perhaps, but the song long transcended Dylan's legacy and remains an anthem for a generation.

When it comes to pure songwriting, "Visions of Johanna" has long been praised as perhaps Dylan's shining moment from Blonde on Blonde. Another Dylan poem put to music, though the debate about what the song's meaning lives on, the words flow beautifully amid the complexity of the composition. While there's room to argue, it would be hard to argue Dylan isn't the greatest to write a ballad. The Grateful Dead often covered the song live while touring during the 1980s and '90s. 

We've mentioned the emotion that Dylan can exude through his music. Dylan meshes love and pain together when it comes to "Shelter from the Storm" off 1975's classic Blood on the Tracks. It's been described as a song about salvation and the grueling process that comes along with the achievement. Not to mention the complex nature of a piece that essentially features just three chords but is executed brilliantly. 

Professional music critics and historians have long contended this was the song that elevated Dylan from a folk star to a rock star. Included on his 1965 Highway 61 Revisited, "Like a Rolling Stone," which happens to be one of Dylan's most confrontational tunes, generated more than ample mass appeal and is arguably his most accessible track. In 2021, Rolling Stone ranked this No. 4 on its "500 Greatest Songs of All Time," and legend has it that this was the song that sparked Bruce Springsteen's dreams of becoming a rock star.

The closing number to Highway 61 Revisited, "Desolation Row" clocks in at a lengthy 11 minutes, 21 seconds. The song's composition is highly complex, involving several characters and some surreal lyrical imagery that touches on disturbing topics. Perhaps the length of the track kept it from enjoying consistent commercial success, but the song's impact has left a lasting impression on various artists, such as emo rockers My Chemical Romance, which released its unique version in 2009.

Choosing the best Bob Dylan is essentially impossible and based on personal preference and taste. However, "Tangled Up in Blue," the undisputed highlight of Blood on the Tracks, seems to encapsulate everything Dylan is about musically — creative and detailed lyrical imagery, enthralling characters, and sound instrumental accompaniment. It has an unmistakable folk vibe but plenty of rock sensibilities, allowing Dylan to become perhaps the greatest musician of all time.