My 25 Greatest Songs

Coming up with a list of great songs is pretty easy. But the greatest songs? Of all time? That’s not so easy.

I completed my first draft in about a day and it had 27 songs on it. There were a few question marks and either/or selections. I chose not to include any classical or instrumental songs, and the date range is 1956-2004. I feel like the last 15 years is too recent to really contend with songs that are 50 years old; I don’t think we can accurately judge or rate recent songs with those that have stood the test of time. That said, I included some more contemporary artists because to my ears, their songs are truly great enough to be on my list. And that’s all it is: my list.

Another caveat is cover versions. As we heard on the XPN countdown, Jeff Buckley’s version of Hallelujah wasn’t quite as great as Leonard Cohen’s original, but the last time they did a countdown in 2014 it ranked higher. I considered several cover songs, and listened to both the cover and original before I decided.

Here’s a link to a Spotify playlist that lists the songs in chronological order. I opted not to rank the songs #1-25 because it was just too hard. And for the most part, each song segues very nicely into the next. Turn up the volume and read on to find out why I chose certain songs.

First up is Elvis Presley’s version of Blue Suede Shoes. I initially wanted to choose Carl Perkins’ original, but couldn’t deny that Elvis’s version is the greater one (even though he didn’t think so!). I thought of other favorite songs and artists from the 1950s, like Jerry Lee Lewis, and for whatever reason they didn’t make the cut. Chuck Berry did though, in part because of how the song Johnny B. Goode is used in the movie Back to the Future. This song also ranked #7 in Rolling Stone’s 500 Greatest Songs of All Time list, which I only looked at after coming up with my draft.

For Blowing in the Wind, I chose Peter Paul and Mary’s version over Bob Dylan’s original, in part because it was released first and I think it’s the defining version of this song. Besides, Dylan appears a few spots later with Like a Rolling Stone (which Rolling Stone magazine declared to be the #1 greatest song in 2004 and again in 2010). Ring of Fire wasn’t an immediate choice, but it made the list in part because of the story behind the song.

(I Can’t Get No) Satisfaction, by the Rolling Stones, is perhaps my favorite Stones song, and that’s ultimately why I chose it over any other song by the band (it’s #2 on the top 500 list). The rest of the 1960s are summed up with two songs from 1967: Somebody to Love, by Jefferson Airplane, and A Day In The Life, by the Beatles. The former was overlooked by XPN fans and didn’t make the top 100 in Rolling Stone, but I think it’s the defining song of the Summer of Love and that’s why it made my list. For the Beatles pick, I went with what came to mind first rather than stressing over all the great Beatles songs. It’s not my favorite Beatles song, but I love how it features both John and Paul and then the seemingly never ending last chord.

If I was ranking the songs, I think Imagine would be my #1 pick. I remember writing the lyrics in red marker on the brown paper bag covering my history textbook in high school, and it feels like a song that transcends every other song on this list if not other lists.

Next up is a bit of a wild card: Harry Nilsson’s Without You. But it was Mariah Carey’s 1993 version that came to mind first, because that was what I first heard as a teenager and I immediately ordered the album from Columbia House. However, when I compared it to the original, the choice was clear.

Lou Reed is near and dear to my heart, and while I was leaning towards choosing a Velvet Underground song, I think Walk On the Wild Side is a stronger candidate for the overall list. The next two songs, Bohemian Rhapsody and Hotel California, are songs that I will always listen to when I hear them on the radio. For a while I considered Hotel California to be a guilty pleasure, but there’s no reason to hide the fact that I like this song.

Ah, Boston. A true staple of classic rock, More Than a Feeling is one of my favorite songs, and my early memory of the song involves one of those TV commercials for a compilation of AM hits or some such package. I really wish I could find this commercial to relive the memory! If you need any convincing as to Boston’s greatness, let me direct you to this essay by Bob Lefsetz.

Billy Joel and the Bee Gees are two spots that I could easily replace with different songs, whether by different artists or not. Just as with the Beatles, there were too many great Billy Joel songs to consider, so I went with my first thought. Stayin’ Alive is another radio favorite that I listen to with glee whenever it comes on.

Since I couldn’t feature every great artist on this list, I picked Because the Night as a way to include Bruce Springsteen while also paying tribute to one of punk rock’s great artists, Patti Smith. After completing the list I realized I didn’t include any other punk songs, and I wonder why that is.

This brings us to the fact that there are technically 26 songs on my playlist. The reason is that Another Brick in the Wall, pt. 2, is simply not as great without the preceding song on the album. My favorite radio stations play them as if it was one track, and indeed, I didn’t realize that they were two distinct tracks until building this playlist.

It was so hard to narrow down the 1980s to just a few great songs, so I went with Eye of the Tiger as my anthem of choice. The Beastie Boys are a group that I’m continuing to discover how much I like them, and I feel like Fight For Your Right perfectly captures the bratty attitude of teenagers in the 80s (if not of all generations). My Madonna selection was a touch choice, so I opted for a personal connection to this song, which I first heard on the playground when I was in 5th grade.

Smells Like Teen Spirit was an easy choice, as was Losing My Religion. I then jumped 10 years to 2001 for Ryan Adams, which was the second song I wrote down on my draft. New York, New York is a song that may not truly rank against the others on my list, but maybe it will with time. It’s a song that reminds me of everything that is great about New York City, so therein lies its greatness.

The final song on my list is the real outlier though. Yeah! by Usher was undeniably the biggest song of the summer of 2004, and I love everything about it. I don’t know enough about hip hop to offer more of a reason, but I think it still holds up today as a really good song, if not great.