My Top 25 Songs of All Time: An IPWatchdog Fourth of July Tradition

By Eileen McDermott
July 4, 2019

Happy 4th!


IPWatchdog has been publishing readers’ and staff picks for the Top 25 songs of all time for the past four years on the Fourth of July. See previous posts here, here, here, and here. Not one to snub tradition, this year it’s my turn.

I was raised chiefly in the 1980s and 90s, but my heart has always been with 60s/70s folk music and classic rock (while my tween friends were fawning over NKOTB I was renting Yellow Submarine and Help! at Blockbuster). At nine years old, my father took me to Tower Records to purchase all of his favorite Beatles albums on cassette—loving the Beatles is passé now, but it’s sentimental in my case. The first song I fell in love with was Maxwell’s Silver Hammer, because it’s silly, and I was nine. That one didn’t make the list, but the Beatles—and Lennon specifically—set the standard for my musical tastes going forward, lyrics being key.

This exercise was much harder than I expected, and my final list looks nothing like I thought it would off the top of my head. There are so many great songs across so many genres and eras from a musical and lyrical perspective that it would be impossible to choose—so in the end I just went with the songs that have had personal meaning to me throughout my life. Some of them may not be so technically “top”, but this list is all about the memories.

  1. “Because” through “The End”, The Beatles, Abbey Road – I know this is more than one song, but each track flows into the next, and at nine I was fascinated by the abrupt shifts in music and the elusive lyrics; the jacket didn’t include the words, and in 1985 or so, that meant you just had to figure it out. I tried, but “Polythene Pam,” “Mean Mr. Mustard,” and “She Came in Through the Bathroom Window,” were tough ones for an American nine-year old from Queens. I considered it a project and would continuously rewind and write down what I heard until I thought I had it right. I remember one line I guessed: “Get a dose of Eddie Jack to Be Built/ She’s still a dilly when she dances the jilt.” (Actual lyric: “Get a dose of her in jackboots and kilt/She’s killer-diller when she’s dressed to the hilt”). I was plagued until adulthood by the line, “Keeps a ten-bob note up his nose.”
  2. A Day in the Life, The Beatles – I was fascinated by this song and better able to discern the lyrics, which I thoroughly enjoyed singing along to. I had no idea it was iconic and considered myself profoundly unique for knowing about it.
  3. While My Guitar Gently Weeps, The Beatles –Even as a young kid, the guitar solo and lyrics in this song made me cry. Sorry, this is the last Beatles song for now!
  4. Fast Car, Tracy Chapman – I became obsessed with her eponymous album around the year it came out, 1988. She writes such haunting and powerful songs that the listener feels transported to the scenes she describes.
  5. Untouchable Face, Ani DiFranco – I followed Ani around the East Coast for a while in my early 20s. In shows from Florida to Boston she played the guitar like a beast; she’s funny and bold and a great storyteller. She’s a poet first and foremost, so her songs are always lyrically genius. I’m picking this song because I have to choose one, and because it makes good use of a bad word (better I think than Erik Brunetti at least).
  6. And I Am Telling You, Jennifer Holliday – go watch Holliday’s performance in the original Dreamgirls from 1985 right now and then remember she did that every night and twice on Sunday for two years. This is one that just fills me with awe every time I hear it because of the sheer talent required to perform it.
  7. Breathe Me, Sia – if you’ve never heard this song before, the only acceptable way to listen to it for the first time is to watch the entire series Six Feet Under right now and then listen to it during the final episode as you cry uncontrollably while contemplating your own mortality.
  8. Cat’s in the Cradle, Harry Chapin – this one always made me cry as a kid too. I thought the son was so mean and felt really bad for the father.
  9. Like a Rolling Stone, Bob Dylan – at some point, I called a 900 number and ordered one of those “Best of the 60s” compilations they used to sell on TV, and it included the lyrics to this song; I immediately fell in love with its Beat Generation vibe and promptly committed it to memory.
  10. Leader of the Band, Dan Fogelberg – I think this was played during my grandfather’s funeral when I was four, so it has always had a strong effect on me when I hear it. I remember listening to it in my room at around age 11 and for the first time understanding what it was really all about.
  11. Across the Lines, Tracy Chapman – same as above. This song has particularly great lyrics.
  12. Bobby McGee, Janis Joplin – somewhere in the midst of teenage angst I was in my car wishing I could run away like Janis and Bobby McGee.
  13. Gloria, Laura Brannigan – I just remember belting this song out with my father in the car as he drove me to kindergarten. I had no idea what the lyrics were beyond “Gloria!”
  14. Dance with Somebody, Whitney Houston – lyrics be damned, Whitney doesn’t need them. Everyone should watch the documentary Whitney to learn more about her heartbreaking but incredible story.
  15. Close Your Eyes, Michael Bublé –this would NOT normally be on my list, but on July 28, 2014, I danced with my wife to this song at our wedding. Turns out wedding planning, like marriage, requires compromise. 🙂

The rest are self-explanatory based either on explanations already provided above or their obvious greatness:

  1. Hey Jude, The Beatles
  2. Big Yellow Taxi, Joni Mitchell
  3. 32 Flavors, Ani DiFranco
  4. Both Hands, Ani DiFranco
  5. Walk On the Wild Side, Lou Reed
  6. Both Sides Now, Joni Mitchell
  7. Because the Night, Patti Smith/Bruce Springsteen
  8. Gloria, Patti Smith
  9. The Sound of Silence, Paul Simon
  10. Smells Like Teen Spirit, Nirvana

The following honorable mentions are all over the map and in no particular order, but all songs I think are great for various reasons:

  • Bohemian Rhapsody, Queen;
  • Ring of Fire, Johnny Cash;
  • Friday I’m in Love, The Cure;
  • Jumpers, Sleater-Kinney;
  • Chop Suey, System of a Down;
  • So Far Away, Carol King;
  • Bridge Over Troubled Water, Simon & Garfunkel;
  • Rhiannon, Fleetwood Mac;
  • Simply the Best, Tina Turner;
  • Space Oddity, David Bowie;
  • Scenes from an Italian Restaurant, Billy Joel;
  • Cream, Prince;
  • This Woman’s Work, Kate Bush;
  • My Sweet Lord, George Harrison;
  • Jeremy, Pearl Jam;
  • A Whiter Shade of Pale, Annie Lennox;
  • Rapper’s Delight, Sugar Hill Gang;
  • Wildflowers, Tom Petty;
  • The Boxer, Simon and Garfunkel;
  • In My Life, The Beatles;
  • Teach Your Children, Crosby Stills & Nash;
  • If Not for You, Bob Dylan;
  • At Last, Etta James;
  • Seasons of Love, Rent.

Images Source: Deposit Photos

Vector ID: 3638456
Copyright: vikhr15

Image ID: 13962832
Copyright: ginosphotos1 


The Author

Eileen McDermott

Eileen McDermott is the Editor-in-Chief of Eileen is a veteran IP and legal journalist, and no stranger to the intellectual property world, having held editorial and managerial positions at several publications and industry organizations. She has acted as editorial consultant for the International Trademark Association (INTA), chiefly overseeing the editorial process for the Association’s twice-monthly newsletter, the INTA Bulletin. Eileen has also served as a freelance editor for the World Intellectual Property Organization (WIPO); as senior consulting editor for the Intellectual Property Owners Association (IPO) from 2015 to 2017; as Managing Editor and Editor-in-Chief at INTA from 2013 to 2016; and was Americas Editor for Managing Intellectual Property magazine from 2007 to 2013.

Warning & Disclaimer: The pages, articles and comments on do not constitute legal advice, nor do they create any attorney-client relationship. The articles published express the personal opinion and views of the author and should not be attributed to the author’s employer, clients or the sponsors of Read more.

Discuss this

There are currently 14 Comments comments.

  1. Kevin Noonan July 4, 2019 5:29 pm

    Respectfully, “Walk on the Wild Side” was Lou Reed, not Bob Dylan

  2. Pro Say July 4, 2019 6:12 pm

    In A Gadda Da Vida

    Full version of course.

    Will never be another one like it.

    ’nuff said. 🙂

  3. Stephen Potter July 5, 2019 5:06 am

    Disappointed not to see anything from the Good Captain – Troutmask Replica is obviously not your cup of tea!!

  4. Concerned July 5, 2019 5:59 am

    Sorry Pro Say….

    Routine, conventional and well understood. Rejected under Alice, EPG, etc.

    SCOTUS (although all 9 of us have it on our iPods)

  5. Sujit Kumar July 5, 2019 6:08 am

    Great List.
    Being an Indian, it was difficult for us to get the lyrics back then by just listening to songs. Did not know it was a global issue that time.
    How things have changed over time!

  6. Benny July 5, 2019 7:53 am

    Great playlist. Every time I hear “cats in the cradle” it pulls at my concious telling me I should be a better Dad and spend more time with my boys.

  7. Pro Say July 5, 2019 10:11 am

    Concerned @ 2: Hilarious!

    Benny @ 3: I’m with you. A great reminder for all men (and women) to give most of our attention to that which is immeasurably more important then even that confounding and unconstitutional Alice lady … our families.

  8. Brad Olson July 5, 2019 11:39 am

    Eileen; excellent choices and I agree with many of them. Pro Say is right about Iron Butterfly …you need a Top 100 next year. Glaring omissions IMHO include some “back in the day” driving classics like BTO’s, “Roll On Down The Highway”; Golden Earring’s “Radar Love” and anything early with Dave Mustaine as guitarist.

  9. Old Examiner July 7, 2019 10:30 am

    A top 25 list isn’t one w/o The Who, Led Zeppelin, The Eagles, The Doors, The Stones, Tom Petty, CSN&Y & some others. In fact, most, if not all, of the top 25 could be made up of just their music.

  10. Eileen McDermott July 7, 2019 7:59 pm

    Woops. Thanks Kevin. 🙂

  11. Anon July 8, 2019 8:36 am

    It also seems to be an annual tradition that some think that one person’s personal (and necessarily subjective) list is somehow “wrong” in an objective manner because it does not match their own subjective views.

    A most odd “admission” of a lack of understanding of the topic

  12. concerned July 8, 2019 9:51 am

    Try to name the top 50 bands of all time and inevitably a person leaves out a glaring “hall of fame” band such as Journey for example.

    These types of list are fun even with all the great songs that makes an inclusive list impossible. Thank you sharing your list Mrs. McDermont.

    Pro Say: I wonder what a top 25 list of inventions would look like on inventions deemed non-patentable under today’s Alice? Whereas, the 9 SCOTUS justices would use post haste. For example, I place a generic computer on a shoebox and it somehow curses some horrible disease.

  13. Christopher Wight July 8, 2019 11:47 am

    How about adding all these to a Spotify playlist, so we can all listen to your list with the press of a single button?

  14. afp August 4, 2019 6:39 am

    A bit late but I have to say, your list leads me to suspect that, first, we must be the exact same age and, second, we would be fast friends. Great taste, imho. 🙂