220px-Bob_Dylan_-_The_Freewheelin'_Bob_Dylan#12 – Bob Dylan – “Blowin’ in the Wind” – (1963)

If you think of it in terms of career longevity, this might be the “newest” song on this 1963 list. While most of the top songs of 1963 are the sort of the end of their era, this was a beginning. This is from his second studio album and wasn’t necessarily a big hit in its day, but has quite a legacy, being named #14 on Rolling Stone‘s “500 Greatest Songs of All Time” list.

bob_dylan_-_the_times_they_are_a-changin#21 – Bob Dylan – “The Times They Are a-Changin'” – (1964)

In 1964 the times certainly were a-changin’. Socially, politically – and musically. If you look at the lists we’ve done from 1965 through 1969, the songs were heavier, more politically charged. But this song was sort of the turning point. Everything from here back is just… simpler. Compare #1-20 in 1964 to 1966 and you’ll likely notice a big difference in tone.

bob_dylan_-_highway_61_revisited#1 – Bob Dylan – “Like a Rolling Stone” – (1965)

Well if Rolling Stone magazine rates a song as the greatest song of all time, it’s hard to argue that it shouldn’t at least be the top song from the year in which it was released. But part of me thinks they just did that because it has the title of their magazine in the song title. I will say, when I came up with the rankings for 1965, I did not know that Rolling Stone had ranked this #1. This is Dylan’s signature song – and probably the best thing he ever recorded himself (let’s be honest, sometimes his songs are best covered). This song sort of encapsulated an era – it was the beginning of the unrest that was channeled through America’s radio and record players. Music before this was much… happier, and simple. This was the start of the turbulence – and you can hear it in his voice (even though the song isn’t about Vietnam or any of the social upheaval of the era, but a woman).

Bob_Dylan_-_Blood_on_the_Tracks#6 – Bob Dylan – “Tangled Up In Blue” – (1975)

This is one of Bob Dylan’s best songs and one of his biggest hits, peaking at #31 on the Hot 100. You can actually understand him too, which is nice. It’s a song that shows just how good Bob Dylan was in his prime. The lyrics – which tell a story in an interesting fashion – are delivered almost non-stop, which is impressive for an almost six minute song. There’s barely even a chorus. It’s just a story – that rhymes brilliantly – and moves around from perspective to perspective. You’ll find a new respect for this track if you really try and follow the lyrics.


USA for Africa – “We are the World” – (1985)

Charity singles. The U.K. goes crazy for them and has them all the time. It doesn’t work so well here in the U.S. Perhaps it’s because this track. I’m not sure. It’s definitely cheesy and a part of 1980s culture. This was a group of singers who came together to perform a song written by Michael Jackson and Lionel Richie and sell it to raise money for famine relief in Ethiopia. The whole thing was inspired by Band Aid (from the U.K.). It ended up raising $100 million and selling over 20 million copies (impressive). Annoyingly, USA for Africa stands for “United Support of Artists for Africa” and that’s because a few of the artists weren’t American. Here’s everyone other than Jackson and Richie who were involved: Dan Aykroyd, Harry Belafonte, Lindsey Buckingham, Kim Carnes, Ray Charles, Bob Dylan, Sheila E., Bob Geldof (who was responsible for Band Aid), both Hall and Oates, James Ingram, Jackie Jackson, La Toya Jackson, Marlon Jackson, Randy Jackson (the one from the Jackson 5… not the one from American Idol), Tito Jackson, Al Jarreau, Waylon Jennings, Billy Joel, Cyndi Lauper, Huey Lewis and the News (the whole band), Kenny Loggins, Bette Midler, Willie Nelson, Jeffrey Osborne, Steve Perry, all three Pointer Sisters, Smokey Robinson, Kenny Rogers, Diana Ross, Paul Simon, Bruce Springsteen, Tina Turner, Dionne Warwick, and Stevie Wonder. Yeah, pretty impressive. Look at how many of those people are respectable and/or legendary (many of them) and think about how that would play out today. Do we really need Bieber and Kesha and company coming together for charity? That’s the exact reason charity singles don’t work in the U.S. anymore. The current crop of North American are trash. Also: not how hilariously out of place Bruce Springsteen and Bob Dylan sound here.