The Most Influential Pop Songs, Ranked By Iconic Songwriter Bob Dylan

Dylan's new book, The Philosophy of Modern Song, is a meditation on 66 songs that changed the social landscapes in music.

Sixty years ago, one of the greatest songwriters of all time released his self-titled debut album, Bob Dylan. Since then, the 81-year-old has amassed Pulitzer and Nobel Prizes, a Presidential Medal of Freedom, 125 million records sold and hits (like “Blowin' in the Wind,” “The Times They Are a-Changin,’” “Like a Rolling Stone” and “Girl From the North Country”) whose influence on music cannot be overstated. This week, he’ll publish his first book since 2004, The Philosophy of Modern Song (Nov. 1, Simon & Schuster), a meditation on 66 songs from a range of artists and styles that changed social landscapes in music. (He’s also enlisted Hollywood stars, including Jeff Bridges, John Goodman, Helen Mirren and Renée Zellweger to narrate the audiobook version.)

“In the same way that Velcro was invented after the Swiss engineer George de Mestral was made curious by the thousands of burrs that were attached to his woolen coat and dogs’ fur, music naggingly adheres itself in countless pinpoints of memory and emotion,” Dylan writes. “People can keep trying to turn music into a science, but in science, one and one will always be two. Music, like all art, tells us time and again that one plus one, in the best circumstances, equals three.”

Here are Dylan’s musings on some of the most important songs of our time.

Related: A Look at Bob Dylan's Lyrics Through the Years

The Most Influential Pop Songs, According to Bob Dylan

“Jesse James” (1928), Harry McClintock

A 19th century folk song about the outlaw leader of the James–Younger Gang, which reveres him as an American Robin Hood, it was McClintock, a railroad worker, actor, singer and spellbinder for the Industrial Workers of the World, who recorded the most recognized rendition. It was first put to wax by Bentley Ball in 1919 and is most often performed instrumentally.

Dylan’s thoughts: “Criminals can wear badges, army uniforms or even sit in the House of Representatives. But an outlaw has no protection from any group. Rap stars, country outlaws, hedge fund scammers and mafiosos live in the lap of luxury while real gangsters like Jesse James hide in the shadows and fear death around every corner.”

“Whiffenpoof Song” (1947), Bing Crosby

“Baa! Baa! Baa!” The traditional closing number of the Yale a capella group the Whiffenpoofs is derived from the Rudyard Kipling poem “Gentlemen-Rankers.” The poem was first set to music in 1885, then transcribed to sheet music in 1909. Crosby recorded his take with Fred Waring & the Glee Club and performed it with Bob Hope in the 1952 film Road to Bali. (It was also featured heavily in the 1949 war flick 12 O'Clock High.)

Dylan’s thoughts: “A lot of bones and skeletons in this song. Even the word Whiffenpoof is a word to dispel spirits, and the melody is ancient. This is a song sung by dues-paying members of the inner circle. Bing sings this so straight, not a wink or a bit of irony, that you think it must have deeper meaning. Sing it and it becomes entirely yours.”

“Come on-a My House” (1951), Rosemary Clooney

Based on an Armenian folk song and with lyrics about traditional Armenian food and hospitality customs, Clooney first performed this track for an off-Broadway production of The Son before releasing it herself and singing it in the 1953 film The Stars Are Singing. (And remember when Boot Miller sang it into a faux-microphone ladle in M*A*S*H, thinking he himself was actually Clooney?)

Dylan’s thoughts: “This song is gesturing at you to discover yourself. It’s coaxing you, enticing you to come out of retirement and jump in. Are you tempted? You bet. But you’re not thinking about what will happen if you’re lured in there, you’re thinking about what could happen.”

“Your Cheatin’ Heart” (1953), Hank Williams With His Drifting Cowboys

Williams had just ended his turbulent marriage with Audrey Sheppard when he was retelling their story to new girlfriend and soon-to-be wife Billie Jean Jones on a drive to Shreveport, Louisiana. He instructed her to grab a notebook and dictate the lyrics he thought up right then. The track was recorded at Williams’ last session in Nashville’s Castle Studio before dying of a drug- and alcohol-induced heart attack soon after. “Your Cheatin’ Heart” was released posthumously.

Dylan’s thoughts: “The song seems slower than it is because Hank doesn't let the band lead him. The tension between the chug of the near-polka rhythm and the sadness in Hank’s voice drives it home. Hank is one of those rare artists that can sing anything and make the song his own.”

“I Got a Woman” (1954), Ray Charles

Existing in many iterations is Charles’ gospel, jazz and blues–influenced soul classic about a woman “way over town that’s good to me.” It’s built on the Southern Tones’ “It Must Be Jesus” and Big Bill Broonzy's “Living on Easy Street;” was covered by Elvis Presley and the Beatles; and is sampled, with Jamie Foxx singing, in Kanye West’s “Gold Digger.”

Dylan’s thoughts: “Traffic was already stop-and-go even without the traffic signals’ being against him. Was gonna take three hours at this rate. Probably could’ve stopped and had dinner after leaving work and gotten there at the same time. But she was waiting for him.”

“Tutti Frutti” (1955), Little Richard

Written by Richard alongside Dorothy LaBostrie, it’s Mojo magazine's No. 1 record on its ranking of 100 records that changed the world. With Richard’s iconic upbeat blues-boogie style, it arguably created rock ‘n’ roll as we know it today.

Dylan’s thoughts: “He took speaking in tongues right out of the canvas tent and put it on the mainstream radio. He’s saying that something is happening. The world’s gonna fall apart. He’s a preacher. ‘Tutti Frutti’ is sounding the alarm.”

“Volare (Nel blu, dipinto di blu)” (1958), Domenico Modugno

Philly sound singer Bobby Rydell had a hit with this Italian tune, but it was Modugno’s original version that won the first ever Grammy for Record of the Year and Song of the Year at the 1959 inaugural ceremony. Co-writer Franco Migliacci drank too much wine and fell asleep; when he woke up, he saw two paintings by the modernist Marc Chagall and was inspired to write the lyrics.

Dylan’s thoughts: “Supposedly it’s about a man who wants to paint himself blue and then fly away. Volare, it means, Let’s fly away into the cielo infinito. Obviously, the endless sky. The entire world can disappear but I’m in my own head.”

“Beyond the Sea” (1959), Bobby Darin

Originally a 1946 French chanson (“La Mer”) by Charles Trenet, this English-language rendition flips the subject from the beauty of looking out over the water to a faraway love. It also reflects on Darin’s troubled childhood, when he learned his sister was actually his mother. You can spot it in the films Every Girl Should Be Married, Goodfellas, Finding Nemo and A Quiet Place Part II.

Dylan’s thoughts: “Darin could sound like anybody and sing any style. Some people create new lives to hide their past. Bobby knew that sometimes, the past was nothing more than an illusion and you might just as well keep making stuff up.”

“Blue Bayou” (1963), Roy Orbison

Who knew this international hit about yearning for home, written by Orbison and Joe Melson and further popularized by Linda Ronstadt’s 1977 cover, would enter the baseball lexicon? It’s why a fastball (blew-by-you) is known as a “Linda Ronstadt” and why former Minnesota Twins broadcaster Herb Carneal would say “Thank you, Roy Orbison” after a last-pitch-heater strikeout.

Dylan’s thoughts: “You want to get back to Blue Bayou. Back to happier times. Where you can put both oars in the water and balance yourself. Back to where you can bait your hook, cast your net, sail around on your skiff and be a seadog.”

“Don’t Let Me Be Misunderstood” (1964), Nina Simone

“Don’t Let Me Be Understood” has seen a variety of versions, from blues-rock (the Animals) to disco (Santa Esmeralda), but Simone carried this tune with her signature voice, a slow tempo, a harp-and-orchestra arrangement and a subtext for the ongoing civil rights movement.

Dylan’s thoughts: “This is a song of crossed wires and false ideas. Being misquoted and things being taken out of context—things lost in translation, people getting a wrong impression of what you’re about. You don’t want to be taken for granted, above all by someone you love. The thing about being misunderstood is that it diminishes your enjoyment of life.”

“My Generation” (1965), The Who

About finding your place in the world and hoping to die before you “get old,” this song of youthful rebellion, written by guitarist Pete Townshend, helped inspire the anti-establishment counterculture of the 1960s.

Dylan’s thoughts: “[Townshend] hopes he dies before he is replaced like he is replacing them. That fear is perhaps the most honest thing about the song. We all rail at the previous generation but somehow know it’s only a matter of time until we will become them ourselves.”

“Truckin’” (1970), Grateful Dead

The United States Library of Congress recognized “Truckin’” as a national treasure of the U.S.; with references to “long, strange” trips, marijuana raids and finding love, it was written by four of the band’s members: Jerry Garcia, Bob Weir, Phil Lesh and Robert Hunter.

Dylan’s thoughts: “The lyrics just pile up on top of each other. But the meaning is understandable and clear. ‘Truckin’—it conjures up something different from traveling. It’s arduous. But the Dead are a swinging dance band, so it doesn’t seem like hard work to go with them.”

“Gypsies, Tramps and Thieves” (1971), Cher

In this title track containing a slew of epithets hurled at a traveling-show family, a 25-year-old Cher speaks from the perspective of a 16-year-old pregnant Romani girl, tackling themes of racism, prostitution and financial instability. It was Cher's first solo number-one single on U.S. and Canadian charts and, at release date, MCA Records’ highest selling song in history.

Dylan’s thoughts: “This is a song about being born on the move. There’s never been a day when you haven’t woken up and said that this wasn’t going to be a good day. This song takes place on the dividing line between the old culture and the new. Probably one of the last traveling medicine shows.”

“London Calling” (1979), The Clash

Amidst World War II, “London calling” would mean the BBC was about to update you with the latest report via radio. (It’s still the BBC World Service's station identification.) But in the beginning of the post-punk era, The Clash used the phrase to call out police brutality, global warming, the Cold War and “phony Beatlemania.”

Dylan’s thoughts: “Punk rock is the music of frustration and anger, but the Clash are different. Theirs is the music of desperation. A lot of their songs are overblown, overwritten, well-intentioned. But not this one. All hell is breaking loose, but the guy is still living by the river, which gives him some type of hope.”

“On the Road Again” (1980), Willie Nelson

Harkening the spirit of Jack Kerouac’s cross-country-hippie-traveling 1957 novel On the Road, this Grammy-winning song was written on a plane’s barf bag and handed to the executive producer of the Nelson-starring film Honeysuckle Rose.

Dylan’s thoughts: “The thing about being on the road is that you’re not bogged down by anything. Not even bad news. You give pleasure to other people, and you keep your grief to yourself.”

Related: How Bob Dylan Shocked His Fans by Plugging In