20. “Purple Haze” (Jimi Hendrix)

What It’s About: Who knows what any of Jimi Hendrix’s songs are about? There is always the old standby that it’s about drugs and getting high, as attested by the fact that Purple Haze is both a form of marijuana and LSD, drugs that the guitar auteur was no doubt familiar with. The lyric “Excuse me while I kiss the sky,” is also an expression for getting high. Do the math.

Why It’s Great: “Purple Haze” is a marvel of modern rock. It doesn’t have the most inventive lyrics in the world, but then, Hendrix became a legend not because of his poetic prowess, but because no one before or after him could match his skills on the guitar. The song peaked in the U.S. at #65 and in the U.K. at #3, spending 22 weeks in the charts between the two countries. It probably would have reached higher had it not been so far ahead of its time. Rolling Stone Magazine recognizes it as #17 on its 500 Greatest Songs of All Time.

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19. “American Pie” (Don McLean)

What It’s About: When once asked what the lyrics to “American Pie” meant, singer-songwriter Don McLean stated simply, “It means I never have to work again.” After four weeks at the top of the charts, the song eased in to music history with its complex symbolism and heartfelt sorrow. While Buddy Holly, Ritchie Valens, and The Big Bopper are never mentioned by name, most feel that the song is about their 1959 plane crash, in part because McLean dedicated his 1971 album of the same name to Buddy Holly.

Why It’s Great: Very rarely does a work transcend its roots and become something else—something greater. McLean refuses to help out in determining his song’s meaning, and the music world has been enriched for it. In addition to the overwhelming commercial success, this song remains one of the most debated pieces of literature in music history.

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18. “For What It’s Worth” (Buffalo Springfield)

What It’s About: Exploding popular myths starting now—“For What It’s Worth,” was neither a Vietnam War protest song, nor a tune that commemorated the Kent State shootings as it predated the latter event by four years. Stills claims the song is about conflicts between young partiers and police intrusion with the closing of West Hollywood’s Pandora’s Box the catalyst that inspired him to write it.

Why It’s Great: Often covered and used in film, this distinctive hit which single-handedly got Buffalo Springfield inducted into the Rock and Roll Hall of Fame, may not have topped the charts upon release—in fact, it only reached #7 on the Billboard Hot 100—but it later escalated to #63 on Rolling Stone’s 500 Greatest Songs of All Time.

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17. “House of the Rising Sun” (The Animals)

What It’s About: Anyone who thinks they can give you an answer to the plot of this song only half knows what he’s talking about. For starters, the song has been altered and changed for a number of years, some even say centuries. The Animals’ version is often referred to as a song about prostitution, but there is nothing lyrically to indicate this is the case. The only definite is, as South Park’s Mr. Mackey would say, is that gambling and alcohol are bad, m’kay?

Why It’s Great: The first ever folk-rock hit, this one topped charts in the U.S., U.K., Canada, and Sweden. Despite the fact that the song had been recorded and played in live shows by a variety of artists since the early 20th Century, including by artists such as Bob Dylan, it was The Animals’ arrangement that stood out from the pack.

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16. “Walk This Way” (Run DMC)

What It’s About: Ah, the sexual tension of high school! No song illustrates the joys of “losing it” like “Walk This Way.” Originally a semi-successful song of the late 70’s, it didn’t rise to the next level until the rap group Run DMC covered it in 1986.

Why It’s Great: What could Run DMC have done differently to set their version apart? Well, for starters, they brought in Steven Tyler and Joe Perry, the songwriters and original performers from the band Aerosmith. The pairing of rap and rock was at the time largely unheard of, but the results were nothing short of spectacular. Not only did the song break through to the mainstream, peaking at #4 on the Billboard Hot 100 and out-performing the original, but it re-launched the career of Aerosmith, who had pretty much vanished since the end of the Jimmy Carter Era. Its influence continues to be heard on Top 40 radio today.

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15. “Lose Yourself” (Eminem)

What It’s About: Delivered with Eminem’s signature style, “Lose Yourself” is one of the greatest rap songs ever recorded in part because it is so surprisingly accessible while remaining true to its roots. A Rocky-esque anthem, if the Italian Stallion had listened to rap, it was used for the film 8 Mile, which also starred Eminem. The positive message is also surprising considering this is the guy who raps about murdering his girlfriend and anyone he doesn’t like on a regular basis.

Why It’s Great: Infusing a little rock-and-roll with originality for a change, this is not a song of samples and anger, as much of rap is, but one with a catchy beat and a determined story that literally makes you feel one with the underdog. It earned its 12 weeks atop the Billboard Hot 100, and its #1 slot on 24 charts worldwide. It also won Best Song at the 2003 Academy Awards and racked up two Grammy wins in 2004.

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14. “Shape of My Heart” (Sting)

What It’s About: Returning to the Ten Summoner’s Tales album, Sting’s 1993 release, is this song, which has appeared in films such as Leon: The Professional and Lethal Weapon 3. Perhaps one of the most cinematic of Sting’s melodies, the tune could be a feature film itself. The only way I can describe it is as the ultimate loner ballad. And we brooding males dig those!

Why It’s Great: If imitation is the sincerest form of flattery, then consider the R&B and hip-hop communities very flattering as they have sampled this song over ten times following Nas’ “The Message” in 1996. The song was never released as a single, so it didn’t get a chance to prove what it could do on the charts, but of the eleven songs on Sting’s 1994 three-Grammy-winning album, this and “Fields of Gold” are the two with the most staying power.

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13. “Fields of Gold” (Sting)

What It’s About: Each song on the album Ten Summoner’s Tales tells a story. “Fields of Gold” is a tale of carefully chosen lyrics and imagery that takes us into the fields of barley with two young lovers as the years pass. It’s the sort of song that takes you to your own special place every time you hear it; but it also leaves you reflective, and that can be either happy or sad depending on what you have to look back on.

Why It’s Great: With simple piano and guitar musical arrangements, Sting proves with this beautiful and melancholic song just how much can be accomplished with very little. While it would only hit #23 on Billboard’s Hot 100, the song was one of the major releases off Sting’s album, which itself was a darling at the 1994 Grammy Awards. “Fields of Gold” is perhaps one of the most touching love songs ever written.

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12. “Invisible Sun” (The Police)

What It’s About: “I don’t want to spend the rest of my life / Looking at the barrel of an Armalite. / I don’t want to spend the rest of my days / Keeping out of trouble like the soldiers say…” Tensions in Northern Ireland hit very close to home for The Police and on the Ghost in the Machine album circa 1981, they took a departure from lighter fare to sing about it.

Why It’s Great: If music could pierce you like a bayonet, this would be the song that could do it. The haunting aura of the synthesizer along with Sting’s purposely drone-like voice gives one the feeling of oppression. This was also the song that proved the new wave of 80’s bands could be just as viable as the protest artists of the Vietnam Era. The #2 peak in the U.K. didn’t hurt it either, especially considering that the BBC issued a ban for sensitive subject matter.

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11. “Every Breath You Take” (The Police)

What It’s About: “Every breath you take and every move you make / Every bond you break / Every step you take / I’ll be watching you.” By now, it’s no big mystery what this, perhaps The Police’s greatest hit, is speaking about. The narrator of this song is a seriously disturbed individual, who can’t seem to let go. Of course, the haunting and beautiful musical undercurrent makes you think of something different, but there is no getting around the lyrics.

Why It’s Great: Aside from sticking in your head and becoming permanently lodged there, the song elevated what was already a great rock band in The Police and it set Sting aside as a tour de force in the music world. But if that’s not enough for you, how about eight weeks at the top of the U.S. charts, four at the top of the U.K.’s, a Song of the Year win for 1983, a Grammy Award at the 1984 ceremonies, and a deserving #84 slot on Rolling Stone’s 500 Greatest Songs of All Time list!

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10. “Baker’s Street” (Gerry Rafferty)

What It’s About: “He’s got this dream about buyin’ some land / He’s gonna give up the booze and the one night stands / And then he’ll settle down, there’s a quiet little town / And forget about everything.” The song seems to be about how life turns us into zombies, and how we always put off improvements for tomorrow—that “Someday I will” line of thought that causes us to waste time and delay confronting the ugly side of ourselves.

Why It’s Great: This song from former Stealers Wheel front man Gerry Rafferty charted in the U.S. and the U.K., peaking at #2 and #3, respectively. Artists such as Slash from Guns ‘N Roses and the Foo Fighters (whose cover charted in the U.S. at #34) have been influenced by it. It has appeared in the movie soundtracks A Guide to Recognizing Your Saints and Good Will Hunting. The song’s sax portion from Raphael Ravenscroft also single-handedly upped sales and use of the instrument in the years following its release.

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9. “What’s Going On” (Marvin Gaye)

What It’s About: There was great soul music before “What’s Going On,” but nothing dealt with the Vietnam Era like this one. Part of a nine-song concept album of the same name, Gaye’s moody delivery about a vet returning from the war to a society he doesn’t recognize opened doors of personal freedom for the artist’s career and became one of the most covered songs of all time by high-profile artists such as Quincy Jones, Coldplay, and U2.

Why It’s Great: In 2003, Rolling Stone magazine voted the What’s Going On album as number six among the 500 greatest albums of all time. The title cut is where most of the heart, soul, and guts come from. Dealing with drug abuse, poverty, and the Vietnam War, “What’s Going On,” elevated the themes of soul music from personal guy-girl relationships to that of a man trying to find his way back into the changing world. The song also spent five weeks at the top of the U.S. R&B charts, and peaked at #2 on Billboard’s Hot 100.

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8. “The Seeker” (The Who)

What It’s About: “Focusing on nowhere / Investigating miles / I’m a seeker, I’m a really desperate man”—the song seems to be about going through life like a directionless arrow. There is always the need to find your target, but you just don’t know what to pierce. “I ask Bobby Dylan; I ask the Beatles; I ask Timothy Leary / But he couldn’t help me either.” Life isn’t easy, and no one, no matter how great they are, can make your decisions for you.

Why It’s Great: The guitar riffs in this song are unbelievable. It doesn’t matter that songwriter Pete Townshend dislikes it, and it doesn’t matter that The Who have had bigger hits. Play this song 40 years after its 1970 release, and it sounds like it belongs on the same airwaves as the bands it influenced—acts such as Green Day, Judas Priest, Led Zeppelin, AC/DC, Nirvana, The Clash, U2, Van Halen, Aerosmith, Deep Purple, Lynyrd Skynyrd, and Pearl Jam. This song is great because it’s heavy-duty. It is bad-ass and in another 40 years, it will still be.

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7. “City of New Orleans” (Willie Nelson)

What It’s About: The death of the railroad as a primary form of transportation brings with it far greater implications. Not only is it the end of an era, but it is the end for a way of life that many people swore by. The future is coming, and the rest is history. It’s a sentiment that, at some point, we all must face.

Why It’s Great: Never has a song so completely captured the feeling of time moving on without you. Lyrically, it uses the railroad to depict the sense of loss we feel with getting older. Vocally, Nelson’s powerful delivery is one of unmistakable sadness and dignity that isn’t quite as present in Arlo Guthrie’s version. Written by the late Steve Goodman (“You Don’t Have to Call Me Darlin’”), this is a classic of folk-country music.

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6. “Bring It on Home to Me” (Sam Cooke)

What It’s About: With lyrics such as, “You know I tried to treat you right, but you stayed out, stayed out late at night. But I’ll forgive you if you bring it to me. Bring your sweet lovin’. Bring it on home to me,” Cooke was able to give audiences a look at the gritty, authentic, agonizing infidelity, while skirting the uptight codes of morality circa 1962.

Why It’s Great: Not every great song has to be a chart-topper. Ask most R&B singers and songwriters, and they will point you to this 1962 track from Cooke as the greatest soul song ever written. The wailing vocals of Cooke, along with the haunting backgrounds of an un-credited Lou Rawls, make “Bring It On Home to Me,” a song that has gotten better with age. Charting at #13 on the pop charts and going all the way to #2 on the Black Singles Chart, this song’s greatness shows up more in the work of the people it influenced than any success it experienced at the time. It is also considered one of the 500 songs that shaped rock and roll by the Rock and Roll Hall of Fame.

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5. “Billie Jean” (Michael Jackson)

What It’s About: Though Jackson would never speak about the incident, it was linked by biographer J. Randy Taraborrelli to a crazed fan who stalked Jackson and claimed that he was the father of one of her twins. The behaviors escalated to a level that unsettled the King of Pop further when he received a parcel that contained a letter, a gun, and a photo of the crazed fan. In the note, she asked that Jackson kill himself at a certain day and time. She would do the same to their baby and herself, so that they could be together in the next life. Nothing ever became of it, though Taraborrelli claims that the young fan was later admitted to a psychiatric hospital.

Why It’s Great: No matter how you see the man’s character, you can’t deny the appeal of this, his greatest work. With a bass line that is out of this world, “Billie Jean” is a song with staying power. In 1983, when it was originally released, it charted in 14 different countries, making it to #1 in seven. Upon Jackson’s death, the song once again charted in 2009, this time in 15 countries. The first time France only pushed it to #45. Twenty six years later it was that country’s #1 hit.

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4. “Heart-Shaped Box” (Nirvana)

What It’s About: “Locked inside your heart-shaped box”? This sounds like he is a prisoner to obsessive love. “Meat-eating orchids”; “Cut myself on angel hair and baby’s breath”; “Throw down your umbilical noose, so I can climb right back”? Note the contrast between those things that are supposed to be delicate and beautiful (Courtney Love perhaps), and their destructive natures (some think if Love was not directly responsible for Cobain’s death, she must have driven him to it). Her crazy-ass antics before and after Cobain’s death lend credibility to this theory.

Why It’s Great: It may not have been number one everywhere it went, but this song charted 12 different times in 11 countries. That along with the disturbed concrete imagery makes this more than a song. It’s a piece of literature.

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3. “It’s Now or Never” (Elvis Presley)

What It’s About: The desperate urgency of being with the one you love.

Why It’s Great: When you think “Elvis,” crap like “Hound Dog” too often comes to mind. Chances are this isn’t the first song that jumps into your brain; nevertheless, it’s the most successful single the man ever released. It sold over 25 million at the time of its release and topped charts in the U.S. and the U.K. (where it spent nine weeks at #1). It also inspired Barry White to stop stealing tires and start singing songs about love-making, so in turn, Presley was responsible for a whole lot of us guys getting action.

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2. “Here Comes the Sun” (The Beatles)

What It’s About: The lyrics are simple. The melody is infectious. The meaning is uplifting. Dark days will pass, and brighter ones will come again.

Why It’s Great: One of many standout hits from Abbey Road, this song demonstrates the emerging talents of George Harrison, who until that point was not given much creative credit by fans or even his own band mates when it came to songwriting. Over 30 covers later from bands such as U2, Bon Jovi, Coldplay, Yo-Yo Ma, and even Nick Cave and the Bad Seeds, this remains perhaps the greatest band’s greatest effort. And it did all of this without ever being released as a single.

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1. “Paint It, Black” (Rolling Stones)

What It’s About: The lyrics have been open to interpretation for many years. Some see it as a Vietnam War protest song. Others believe drugs are hidden in the underlying meaning. These two themes, whether accurate or not, were blamed on a lot of 60’s music. At its most basic level, the song is about a man mourning the loss of his dead girlfriend.

Why It’s Great: Covered by U2, The Black Dahlia Murder, W.A.S.P., and myriad other bands since its 1966 release, “Paint It, Black” reached number one on Canadian, Dutch, U.K., and U.S. charts. If that’s not great, then what is?

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