Bob Dylan Popular Song Rankings [2026]

Maggie’s FarmBob Dylan43rank/position

Maggie’s Farm – Bob Dylan

A shocking song released in 1965 by American artist Bob Dylan.

Featured on the album “Bringing It All Back Home,” it was later issued as a single.

Symbolizing the transition from folk to rock, this work carries a searing critique of an oppressive society and a soul’s cry for individual freedom.

His performance at the Newport Folk Festival in July 1965 split the audience, who were stunned by the electric sound.

With lyrics that incisively capture the spirit of the times and a powerful melody in perfect harmony, this masterpiece is still covered by many artists and used in films and television dramas.

Make You Feel My LoveBob Dylan44rank/position

Make You Feel My Love – Bob Dylan | Voice: Peter Head | Video Charlie Chaplin – City Light

The organ on this track is played by Augie Meyers, a Texas-born musician known as the keyboard player for the August Douglas Quintet and the Texas Tornados.

This song has been covered by many artists.

MississippiBob Dylan45rank/position

Bob Dylan-Mississippi-Live-Central Point, OR 10-09-2001

The American legendary singer-songwriter Bob Dylan’s 2001 song drew attention as a track on the album “Love and Theft.” Centered on themes of lost love and wandering, it’s a captivating piece that blends Dylan’s characteristically poetic lyrics with a country rock sound.

Rolling Stone praised it as one of the best songs of the 2000s, and it ranked 260th on the list of the 500 Greatest Songs.

Dylan’s powerful vocals and emotive phrasing resonate deeply with listeners.

Closely tied to American values and history, this work is an ideal entry point to Dylan’s musical world.

Mixed-Up ConfusionBob Dylan46rank/position

Bob Dylan – Mixed Up Confusion 76982-5

It’s a track that was released in Japan under the title “A Mix-Up of Confusion.” It’s very up-tempo and features a lot of Dylan-esque phrasing.

At the time, it reportedly wasn’t included on the album in the United States because it didn’t fit Bob Dylan’s image.

Most Likely You’ll Go Your WayBob Dylan47rank/position

Gerry van der Laan, “Most Likely You Go Your Way, (I’ll Go Mine”), Bob Dylan Cover

In Japan, it was released under the title “I Walk My Own Path.” It has a very gentle, bluesy feel, and its tender melody can almost bring you to tears.

The remix released by DJ Mark Daniel Ronson became a hot topic.

Most of the TimeBob Dylan48rank/position

Bob Dylan – Most of the Time (Long Version) (Official Video)

This is a song released in 1989 by the legendary American singer-songwriter Bob Dylan.

Its lyrics, which portray the complex emotions after a heartbreak, have resonated with many and earned high praise from critics.

Featured on the album Oh Mercy, it was also used in the ending of the film High Fidelity.

The calm acoustic guitar tones and Dylan’s distinctive vocals are a perfect match.

Evoking a deep sense of introspection, this piece is a song that can heal the hearts of those who have been hurt.

Mother you’ve been on my mindBob Dylan49rank/position

Bob Dylan – Mama, You Been on My Mind (Live at Harvard Square Theatre)

It’s sung about the girlfriend he was dating at the time.

However, in the lyrics he refers to her as “Mama.” He may have been overlapping the image of his mother and his girlfriend.

The line “Mama is always in my heart” suggests that she is no longer around, which allows us to read the song as a breakup song.

Because it hasn’t been included on many albums, it remains a hidden gem that’s still popular today.

I chose it as an unusual pick—a song about his mother.