Ask A Music Critic: Which Artist’s ‘Biggest’ Song Is Also Their Best?

Welcome to another installment of Ask A Music Critic! And thanks to everyone who has sent me questions. Please keep them coming at

When debating bands and artists, we often consider the totality of their catalogues and careers to form our opinions and arguments. But what would happen if we would judge a band or artist solely based on their biggest hit? Excluding one-hit wonders, which bands and artists’ reputations would be hit the hardest? Conversely, who would benefit the most? For example, The Beatles are the consensus “Greatest Band of All Time,” but what if we could only evaluate them based on “Yesterday”? Led Zeppelin with “Stairway to Heaven”? Prince with “When Doves Cry”? Whitney Houston with “I Will Always Love You”? Radiohead with “Creep”? Pearl Jam with “Last Kiss”? While this isn’t a fair system for judging great artists, I do think it’s interesting to consider whose reputation would take the biggest hit and whose reputation would be over-inflated. — Matthew from Montclair, N.J.

As you admit, this is a highly questionable method for assessing artistic greatness. However, I happen to be a fan of questionable methods for assessing artistic greatness, so let’s get into this!

It should go without saying that the biggest song by a particular artist is rarely the best song. But it’s amazing how wide that gap between biggest and best is for some artists. For instance, Frank Ocean was possibly the most acclaimed artist of the 2010s. He is properly celebrated for landmark albums like Channel Orange and Blonde, but the highest-charting track that Frank Ocean appeared on is “Slide,” a hit for Calvin Harris. Kendrick Lamar is a similar case — in this paradigm, the man who made classics like To Pimp A Butterfly and Good Kid, M.A.A.D. City would be judged by his cameo in Taylor Swift’s “Bad Blood,” just as Bon Iver would be assessed on the strength of Swift’s recent hit, “Exile.”

As for acts that would benefit from this, the group that comes immediately to mind is The New Radicals. (I know you said no one-hit wonders but it’s next to impossible to find over-inflated examples if you don’t look at one-and-done acts.) If you were to judge this band solely on the basis of their only hit, 1998’s “You Get What You Give,” they would be, perhaps, the greatest indie-pop group of the ’90s.

And then there are artists who are considered iconic based on their catalogues … and would still be considered iconic if you only judged them on their biggest hit. If you only looked at “Like A Rolling Stone” when assessing Bob Dylan’s career, he comes out very well. Same with Queen and “Bohemian Rhapsody” — that song brilliantly summarizes everything that was unique and glorious about that band. As for Prince, did he ever make a better song than “When Doves Cry”? People will surely disagree — I’m a “Kiss” man myself — but being judged solely by that song is hardly an insult to the Purple One’s great legacy. I’d say the same thing about Whitney Houston and “I Will Always Love You” — she’s surely not diminished by having that as a signature song.

The point is, there are some artists who are so great that even when you judge them by an extremely flawed standard, they still come out looking like geniuses.

Why do people always scream joyously when artists curse on stage at shows? What makes hearing someone say “fuck” on stage feel more satisfying in a crowd setting? — James from Des Moines

Great question! I can’t believe you’ve actually made me nostalgic for having a performing artist scream obscenities in my face for the benefit of cheap applause. Just another thing to add to the “only in 2020” pile!

Upon reflection, I think there are three reasons why audiences respond so favorably to a well-placed “F-bomb” or “S-bomb” or “C-bomb” — there are multiple C-bombs! — at a show. Let’s explore each one of them.

1) Swearing is awesome

I could stop right here. Swearing is one of the best activities that an individual can pursue. It makes a person seem cool, confident, and admirable. Swearing not only makes everybody love you, but it also earns their respect. Fuck yeah.

2) Our Puritan roots

This country was built by severely repressed and deeply religious people, and while we have drifted far from those roots in the subsequent centuries, the belief that swearing is “naughty” remains deeply ingrained in our national psyche. At the same time, as we’ve already established, swearing is inarguably awesome. So, when we see a person swear in public, we feel a double shot of exhilaration because that person is doing something that is awesome AND defying social conventions, which is also awesome.

3) Swearing is a way to simulate spontaneity in an otherwise highly planned environment

Most concerts are performed by rote — the setlists don’t change, the lighting and staging are fixed, even the better-song patter is often scripted. It’s all part of the facade of a professional show-biz presentation. Swearing, however, is a way to break through that facade, if only for a moment — even when the swearing is part of the script. It’s the same reason why “hip” college professors swear in class. It’s a “shock” move meant to shake the audience of its stupor with a gesture that appears spontaneous and even — here’s that Puritan thing again — outside of what’s normally considered acceptable.

Does that make sense? I’m sorry, I mean: does that make fucking sense? Please, hold your applause, you’re embarrassing me!

Is there any important claim or argument that you have made in one of your books that you would go back and revise? And, as a corollary, as a writer how much to think about how your commentary will age as you’re writing it? — Kyler from Kansas City

This is a hard question, because my books — including my latest, This Isn’t Happening: Radiohead’s Kid A and The Beginning Of The 21st Century, due out next month and available now for pre-order! — are perfectly realized works that are utterly lacking in flaws.

I kid! The truth is that I never revisit my books because I’m afraid of what I’ll find there. It can be scary to put your thoughts down, lock them in, and then be forced to live with them for the rest of your life. I’m sure there are lots of things I’ve written that I would love to revise. But two things come immediately to mind: First, in Your Favorite Band Is Killing Me, I wrote about the rivalry between Michael Jackson and Prince. About a month before the book published, Prince died, which obviously changed the context for his life and career. I would’ve liked to revisit that chapter in light of Prince’s passing. I don’t think it would have dramatically changed my take on that rivalry, but I probably would’ve been more respectful of his output post-Diamonds And Pearls.

Second, in Twilight Of The Gods, I wrote some snarky things about John Mayer in the context of his tenure in Dead & Company. Since that time, I’ve gained a deeper appreciation for both Dead & Co. and Mayer’s solo catalogue. At some point, I’d like to do a deep dive into Mayer’s career, because I think he’s more interesting than he gets credit for. (I realize this might seem like a strange choice — why would I want to be nicer to John Mayer? But it’s honestly one of my main regrets about that book.)

For now, we’ll leave it at those two revisable opinions.

Jewel case or cardboard sleeve for CDs? — Brianna from Alexandria, Va.

Jewel case 4 life.

Some artists covered here are Warner Music artists. .